How to Spend 2 Weeks in Italy (Itinerary for 14 Perfect Days!)

Planning your first trip to Italy may feel overwhelming–but this (repeatedly) tried-and-tested itinerary for 2 weeks in Italy will have you relaxing into la dolce vita in no time!

For those who are new here, we are Kate and Jeremy Storm, travel bloggers and Italy travel addicts who have cumulatively spent more than a year each, over the course of many trips, exploring Italy in-depth.

After more trips (and plates of pasta) than we can count, our desire to return to Italy just keeps growing: there will always be more villages to explore, natural beauty to marvel at, and, of course, pasta and wine to enjoy.

Helping travelers plan their Italy itineraries is one of our passions, and we have repeatedly tested this guide to 14 days in Italy on friends, family, and ourselves many times over the course of several years!

So far, we have personally made our way to 14 of Italy’s 20 regions, from the imposing Dolomites of South Tyrol to the beaches of Sicily.

We’ve also “lived” for 2 months in Rome, and one month each in Florence and Bologna, enjoying a slower pace of Italy travel.

Suffice it to say that after all the time we’ve spent in Italy, we have some opinions about how to make your first trip to Italy truly unforgettable… and this Italy itinerary is what we suggest.

kate storm jeremy storm and ranger storm overlooking brisighella italy
Our dog, Ranger, travels to Italy with us too!
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For first-time visitors, 2 weeks in Italy is the perfect amount of time to hit the country’s most famous and classic spots, see which ones you love, and (if you’re anything like us) fall head-over-heels in love with the country to the point that you’ll leave planning your next trip back.

This is the 2 week Italy itinerary we recommend to first-time visitors, including our friends and family, and we won’t be straying off the beaten path much here.

These first 14 days in Italy will be all about the classics–follow this trip and you’ll be spending a lot of time watching postcards come to life!

(And yes, this is a fairly long Italy blog post–feel free to use the table of contents below this paragraph to jump around as needed.)

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After Planning Your 2 Week Italy Itinerary…

… we’d love to help continue to plan your trip to Italy in more detail here on Our Escape Clause!

We have been writing about Italy travel since 2016, and have amassed a collection of 100+ Italy blog posts available for free on this website, covering everything from the best hidden gems in Rome to what a coperto is (and why you should expect to pay one).

Cities like Rome and Venice are among our absolute favorites in the world, and we write about them extensively–but if you’re interested in getting off the beaten path in Italy, we have lots of options for that, too, from enjoying the mosaics of Ravenna to taking a road trip in Puglia.

kate storm standing on the edge of the island san giorgio maggiore
View of Piazza San Marco from the Venetian island of San Giorgio Maggiore.

One of my favorite things to write is detailed itineraries (like this one!), and we have suggestions for RomeFlorenceVeniceCinque Terre, the Amalfi CoastMilanNaples, and more (and in the cases of some cities, several versions depending on how long you have to explore!).

I’ll link relevant blog posts throughout this 2 week Italy itinerary, but of course, I could never hope to include links to them all!

21 Essential Tips for Eating in Italy (+ How to Decode Italian Menus)

Head to our Italy archives to view all of our Italy blog posts in order, or if you’re looking for details on a particular destination, the search bar at the top right of the page (or at the top of the pop-out menu on mobile) is a great tool to use.

You also may want to check out the comment section at the bottom of this post–over the years, dozens of travelers have refined their own Italy itineraries there!

kate storm in front of a church when traveling in rome italy

How We Structured This Itinerary for 14 Days in Italy

We structured this 2 week Italy itinerary as a point-to-point trip covering Rome, Florence, the Tuscan countryside, Cinque Terre, and Venice.

In this way, you’ll have a chance to experience many of the most popular places to visit in Italy over the course of 2 weeks, without doubling back or over-stuffing your schedule.

The Ultimate Italy Bucket List: 75 Best Things to Do in Italy

While some travelers like to include Milan, Lake Como, and/or the Amalfi Coast over the course of 2 weeks, we have found that with roughly 14 days (and often some jet lag) to work with, less is more.

We’ve opted for Venice over Milan and Lake Como due to personal preference, and opted for Cinque Terre over the Amalfi Coast due to geographic convenience and the ease with which it can be seen over a short period of time.

However, ultimately, the destinations that appeal to you most should be at the top of your Italy bucket list, and this itinerary for Italy in 2 weeks can be adjusted accordingly.

kate storm and ranger storm sitting on a bench overlooking lake como surrounded by flowering trees
Lake Como is certainly gorgeous!

The Perfect Itinerary for 2 Weeks in Italy

Days 1-4 in Italy: Rome

Rome’s highlights rank among the most famous sights in the world: who hasn’t dreamed of seeing the Colosseum in person, of walking across St. Peter’s Square, and of admiring the masterpiece that is the Sistine Chapel?

Three full days in Rome (excluding travel days) will give you plenty of time to see the best of what Rome has to offer, while also leaving plenty of time in your 2 weeks in Italy itinerary for all of the other destinations along the way.

2 Days in Rome: An Epic & Easy Rome Itinerary

If you happen to be lucky enough to have an extra couple of days in Italy, though–say 15 or 16 days, or perhaps less jetlag to contend with than some visitors–we highly recommend extending your time in Rome before adding time to any other destination on this 2 week Italy itinerary.

It’s simply impossible to run out of incredible things to do in Rome, which is why we have happily spent months there!

(It’s also worth pointing out that if you do have a bit of extra time in your schedule, booking an organized day trip to the Amalfi Coast is doable, if a long, day that is popular with ambitious travelers!).

4 Days in Rome Itinerary: Piazza del Popolo

Top Things to Do in Rome

Tour the Colosseum + Palatine Hill.

Strolling through the center of Ancient Rome for the first time is an unforgettable experience!

Definitely don’t miss it during your first trip to Italy: you can buy skip-the-line tickets here (highly recommend for people visiting during summer/high season), or book the tour we enjoyed here.

kate storm in a striped dress in front of colosseum rome italy
Visit Vatican City.

The magnificent Sistine Chapel, the iconic St. Peter’s Basilica, the lovely St. Peter’s Square: for being such a tiny country, visiting Vatican City has a lot to offer!

We recommend using skip-the-line passes here as well, you can purchase them here.

We wrote a full guide to visiting Vatican City, so won’t repeat ourselves too much here, but in short, plan ahead, cover your shoulders, and touring the Vatican Museums on Friday night is worth it if you have the chance.

Map room in the Vatican Museums shot at night, with open window on the left. Visiting the Vatican Museums during special hours is one of our favorite travel tips for Rome Italy!
Stroll through Centro Storico.

The Trevi Fountain, the Pantheon, the Spanish Steps, Campo de Fiori: what do all of these famous things to do in Italy have in common with each other?

30+ Important Rome Travel Tips You Need to Know

They’re all within walking distance of each other in Rome’s Centro Storico!

We also recommend seeking out a few of Rome’s hidden gems as you explore, including easy-to-access spots like Galleria Sciarra and Galleria Spada.

One of the best things about visiting Rome is just how much beauty is hidden in plain sight.

2 Day Rome Itinerary: Street Corner in Centro Storico

Things to Consider When Visiting Rome

Rome has two major downsides for a tourist: crowds and heat.

You can beat the bulk of both by traveling in the shoulder season (we personally think that October is the perfect month to visit Italy, and Rome is remarkably uncrowded in winter), and/or waking up extra early to enjoy the city before everyone else gets out of bed.

19 Best Day Trips from Rome, Italy (+ How to Get There!)

For example, some of the best photos of the Trevi Fountain, Colosseum, and Spanish Steps that we’ve taken were snapped around dawn!

That being said–there are a million ways to get off the beaten path in Rome no matter when you visit!

While touristic hotspots like the Colosseum and Spanish Steps are nearly always crowded, fascinating places like the Capuchin Crypt, the Palazzo Doria Pamphilj, the Basilica of St. Paul Outside the Walls, plus the neighborhoods of Testaccio, Ostiense, and Monti in general, are just a few of the many great places to enjoy Rome without dense crowds.

2 Days in Rome: Trevi Fountain

Where to Stay in Rome


La Cornice Guesthouse — We loved this little guesthouse! It was extremely clean and comfortable, and VERY affordable for Rome.

La Cornice is set slightly outside the main tourist areas, but an easy 5-minute walk to the metro and a 20-minute ride got us to the Colosseum and other major sights.

Our favorite part of La Cornice? Eating a nearby Joseph Ristorante for lunch, which we not only enjoyed during this trip but have returned to repeatedly in the years after.

Check rates & book your stay at La Cornice Guesthouse!
4 Day Rome Itinerary: Campo de'Fiori

Hotel Condotti — Located just around the corner from the Spanish Steps (and consequently the Piazza di Spagna metro station), you couldn’t ask for a better location in Rome!

Well-reviewed and boasting exceptionally clean rooms, Hotel Condotti is the perfect choice for a traveler with a midrange budget (or even a luxury traveler–this hotel also holds some impressive-looking suites!) who would like to be within walking distance of the best that Centro Storico has to offer.

Check rates & book your stay at Hotel Condotti!
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Pantheon Inn — If you’re looking for a building with classic Italian charm in the heart of Rome, this is it.

Located right behind the Pantheon and within reach, the Pantheon Inn offers a quiet, peaceful escape in the middle of bustling Rome.

You will need to walk a bit to the metro stop–but since the walk will take you through the heart of the beautiful Centro Storico, we doubt you’ll mind.

Check rates & book your stay at the Pantheon Inn!
2 Days in Rome: Vatican Museums Spiral Staircase

Days 5-7 in Italy: Cinque Terre

No first trip to Italy would be complete without a visit to this beautiful coastline!

After leaving Rome, head north to Cinque Terre for coastal views, hiking, adorable fishing villages, and plenty of fresh seafood.

The Perfect One Day in Cinque Terre Itinerary

We recommend traveling from Rome to Cinque Terre (specifically Monterosso al Mare) via train, which should take about 4-6 hours depending on the route.

Since all 5 of the Cinque Terre villages are easily connected by train (or ferry during the summer!), feel free to stay in whichever one appeals the most, or even in nearby Levanto or La Spezia to save a tiny bit of cash.

View of Spiaggia di Fegina in Monterosso al Mare with colorful umbrellas in the foreground, one of the best photography locations in Cinque Terre Italy

Top Things to Do in Cinque Terre

Hike between the villages.

Sadly, many of the hikes at Cinque Terre have been closed for landslides–but the magnificent Blue Path trail between Monterosso al Mare and Vernazza (which is highly recommended!) and between Vernazza and Corniglia are open and ready for visitors!

We recommend stopping by one of the visitor centers for the latest information on available hikes.

View of Vernazza Harbor from Above: One Day in Cinque Terre Itinerary
This view of Vernazza, as seen when approaching on the hike from Monterosso al Mare, is unforgettable!
Watch the sunset from Manarola.

Arguably the most famous of Cinque Terre’s villages due to its postcard-worthy view, Manarola is the perfect place to watch the sun sink behind the sea (preferably with a glass of local wine in hand).

17 Quick Cinque Terre Tips You Need to Hear
Eat all the pesto and seafood.

Pesto is local to the Ligurian coast, and that makes Cinque Terre one of the best places to indulge in it in all of Italy!

Pesto happens to be one of my favorite foods, so I may be slightly biased, but in my opinion, it’s an unforgettable part of visiting Cinque Terre.

As the villages of Cinque Terre are fishing villages at their heart, the seafood here is also absolutely delicious.

Woman facing away from camera on Manarola Promenade, One Day in Cinque Terre Itinerary

Things to Consider When Visiting Cinque Terre

While it would be tempting to bring a car to Cinque Terre to have access to your own transportation and a more direct way to get to Cinque Terre from Rome and to Florence after your visit, the roads do not make for an easy drive.

Parking can also be a challenge around the villages–if possible, we’d recommend relying on the train, ferry, or the famous trail to get around Cinque Terre.

15+ Common Travel Mistakes in Italy (What NOT to Do!)

Keep an eye on closures to both the trains and the trails between the villages, however.

Strikes can happen that will shut down the train (which happened to us way back in May 2016!), and the trails can sometimes be washed out and therefore closed.

The trails also often close during the offseason, so if you’re planning a winter trip to Italy, don’t count on being able to hike between all the villages.

2 Weeks in Italy Itinerary: Beach at Monterosso al Mare, Cinque Terre

Why Cinque Terre instead of the Amalfi Coast?

I addressed this above, but it’s understandably a popular question when planning a trip to Italy for 2 weeks, and I wanted to expand on it here!

Italy’s Amalfi Coast is truly a marvel, but it makes less geographic sense for this itinerary than Cinque Terre.

Visiting the Amalfi Coast would require traveling south from Rome when the bulk of this 2 weeks in Italy itinerary focuses on the northern half of the country.

Amalfi Coast or Cinque Terre: Which Sublime Italian Coastline is Best?

If you have your heart set on visiting the Amalfi Coast, you can certainly swap it out for Cinque Terre, but bear in mind that the travel times involved would be cumbersome, especially if you don’t want to cut days from the rest of the destinations on your Italy itinerary.

Cinque Terre also has the benefit of being smaller than the Amalfi Coast, making it easy to explore most or all of the villages over a short amount of time.

If you absolutely don’t want to cut any destinations and are determined to visit both Cinque Terre and the Amalfi Coast, handing the reins to the experts and booking and organized day trip to the Amalfi Coast from here is your best bet (this one gets rave reviews).

View of Riomaggiore at Sunset, Cinque Terre in One Day

Where to Stay in Cinque Terre

Of the 5 villages of Cinque Terre, the only one we would recommend not staying in is Corniglia, as it’s the most difficult to get in and out of.

Other than that, all the villages have their perks–Monterosso al Mare has the biggest beach, Manarola has the most Instagram-famous viewpoint, and Vernazza and Riomaggiore are simply drop-dead gorgeous.

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Bear in mind that many properties in Cinque Terre can involve a climb to reach them, so if mobility is a concern, be sure to double-check the location.

Most properties will offer porters to carry your luggage for you for a small fee, so if clamoring through town with your luggage doesn’t sound like fun, be sure to ask your hotel about their services!

Here are a few very well-reviewed properties to consider during your time in Cinque Terre:

Photo of Vernazza from above, the perfect stop on a 2 week Italy itinerary

Luciano Guesthouse (Riomaggiore) — This is where we stayed during our most recent visit to Cinque Terre, and we can’t recommend it enough!

The property was clean and lovely, and the customer service offered by Francesco and his wife during our stay was absolutely top-notch. We would be thrilled to stay again!

Check rates & book your stay at Luciano Guesthouse!
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Scorci di Mare (Riomaggiore) — Want to stay a 3-minute walk from the beach and see the sea from your window?

If so, the popular Scorci di Mare is the perfect spot for you!

Check rates & book your stay at Scorci di Mare!

Da Baranin (Manarola) — Cinque Terre is expensive, there’s no getting around it.

For a budget option, consider Da Baranin–you’ll need to climb up and down a steep hill as a trade-off, but you’ll get to stay in Manarola for a very affordable price tag!

Check rates & book your stay at Da Baranin!
2 Weeks in Italy Itinerary: Monterosso al Mare, Cinque Terre

Days 8-11 in Italy: Florence + the Tuscan Countryside

Tuscany is one of our favorite regions in Italy–and not just because we could spend a lifetime eating and drinking there (though we could).

The Perfect Tuscany Road Trip Itinerary (+ Important Driving Tips!)

The towns are beautiful and distinct, Florence is a dream of a city, the history is interesting, and the golden tinge to the light that you see in pictures of Tuscany isn’t photoshop–it just really looks like that.

While there’s no such thing as too much time in Tuscany, 3 days in Tuscany will give you a chance to explore the best of Florence in about 1.5-2 days, and also give you time to visit at least one other Tuscan city or small town, and/or head out wine tasting.

kate storm standing in front of florence duomo front doors

Pisa is a popular choice that is close to Florence, but unless you’re truly dying to see the leaning tower, we’d recommend Siena, Lucca, or Montepulciano instead.

How to Enjoy 3 Days in Tuscany: Itinerary Ideas With or Without a Car!

If you’re looking for small-town day trips from Florence, San Gimignano, Volterra, Arezzo, and Montefioralle (near Greve in Chianti) are all stunning, and though it is in Umbria rather than Tuscany, we adored our visit to the village of Orvieto as well.

If you’re hoping to enjoy some wine tasting and town-hopping, this is an excellent opportunity to get a lot of value out of a guided tour: this wildly popular day trip from Florence is a fantastic way to taste a variety of what Tuscany has to offer (literally and figuratively).

2 Weeks in Italy Itinerary: Arezzo, Tuscany

Top Things to Do in Florence

Visit some of the best Renaissance art on the planet.

The Uffizi Gallery (home of the Birth of Venus) and the Galleria dell’Accademia (home of Michelangelo’s David) are both home to undisputed world treasures that deserve to be admired during your 2 weeks in Italy.

The Ultimate 2 Days in Florence Itinerary

We definitely recommend booking skip-the-line tickets to both galleries to avoid waiting in their very long lines (we once showed up to the Uffizi without pre-booked tickets and ended up giving up on visiting after nearly an hour of waiting).

You can purchase skip-the-line tickets to the Galleria dell’ Accademia here and to the Uffizi here.

opulent interior of the uffizi gallery, one of the best things to see in itinerary for italy in 2 weeks
Try your hand at a cooking class.

We may be a bit biased, given how much we adore Tuscan food, but if you want to take a cooking class during your 14 days in Italy, we recommend doing it here.

We adored our day taking this cooking class and years later, we still talk about it being one of our favorite days spent in Tuscany!

From the views of the countryside to the beautiful farmhouse the class is hosted in, to the sublime food, it is truly an experience to remember.

One Day in Florence: Cooking Class in Tuscany
Seek out the best views of the city.

From the ever-popular viewpoints of Piazzale Michelangelo and the cupola of the Duomo to lesser-known spots like the Rose Garden and Palazzo Vecchio, there’s no doubt that Florence is a city that deserves to be admired from all angles.

We’ve rounded up the best views of Florence here–personally, we have a soft spot for the view from the top of Palazzo Vecchio.

What to Do in Florence at Night: 13 Fun Ideas
Take a day trip to the Tuscan countryside.

Wine, plus incredible Tuscan food, plus rolling countryside, plus stunning villages–a day trip to some of Tuscany’s remarkable villages and wineries is bound to be a day that you’ll never forget.

This incredibly popular day trip is a fabulous option!

Honeymoon in Tuscany: rooftops of Siena

Things to Consider When Visiting Florence and Tuscany’s Countryside

Three days in Tuscany gives you a couple of options as far as lodging: you can either stay in Florence the whole time and take day trips out, you can stay in a smaller city the whole time and simply take a day trip to Florence, or you can split it up–two nights in one city, and one in another.

Personally, we’d recommend sticking with one place to stay–this Italy itinerary is already fast-paced, so there’s no reason to take up extra time moving hotels in Tuscany.

We’ve visited Tuscany many times with both structures, and love both for different reasons.

You truly can’t go wrong with either option–I’d stay in Florence if you’re more of a city person, and in a surrounding Tuscan town if you’re more interested in the countryside.

If you stay in the countryside, you will definitely want to rent a car for this portion of your Italy itinerary.

2 Weeks in Italy Itinerary: View of Florence Duomo

Where to Stay in Florence


B&B Le Stanze del Duomo — Though Florence hotels can be a bit pricey and stretch the definition of “budget”, B&B Le Stanze’s beautiful rooms and impeccable location in Florence will be sure to have you swooning!

Check rates & book your stay at B&B Le Stanze del Duomo!
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Hotel Silla — Located just a hop, skip, and jump from the Arno River, we loved our stay at Hotel Silla!

The hotel itself is lovely and quiet, the included breakfast a nice touch, and the location perfect: you have easy access on foot to all that Florence has to offer, without having to worry about crowds or noise.

We’d be happy to check in again!

Check rates & book your stay at Hotel Silla!
kate storm and jeremy storm sitting on the edge of the arno with the ponte vecchio in the background

Hotel Lungarno — Nestled right against the Arno River and home to one of the best views of the Ponte Vecchio in Florence (not to mention some of the best views of the rest of Florence from their top deck), Hotel Lungarno is our personal “if we ever really want to splurge” hotel in Florence.

You can’t go wrong using Hotel Lungarno as your base during your Italy vacation!

Check rates & book your stay at Hotel Lungarno!
Romantic Things to Do in Tuscany: Tuscan streets in rain

Days 12-14 in Italy: Venice

Canals, canals, and more canals: Venice is simply a ridiculously beautiful place, and despite its somewhat controversial reputation, we absolutely adore it (yes, even during the summer!).

Definitely make sure that you climb St. Mark’s Campanile for an amazing view of the city, check out Libreria Acqua Alta (one of our favorite bookstores in the world!), walk across the Rialto Bridge, and spend ridiculous amounts of time wandering aimlessly around the small streets and lesser-known canals–that is truly Venice at its best.

7 Cool Things to Do in Venice’s St. Mark’s Square (Piazza San Marco)

If you have good weather while in Venice, also consider a day trip out to Murano or Burano for another view of Venetian life!

We’ve written extensively about Venice, in large part because we adore the city and know that unfortunately, not everyone walks away with the same impression.

We recommend taking a look at our suggested 2 day Venice itinerary and guide to the best hidden gems in Venice as you plan your trip here!

Small canal in Venice on a sunny day, lined by windows with flowerboxes

Top Things to Do in Venice

Tour the Doge’s Palace + St. Mark’s Basilica.

Venice has a truly fascinating history–for a city that is now known mostly for its beauty, flooding, and risks of sinking, it can be hard to recall that once upon a time, there was a true and powerful Venetian Empire.

Learning about the history of Venice’s government (it included many councils) and how it acquired its wealth is a fabulous way to get to know the city on a deeper level–and the buildings themselves are incredibly impressive, too.

We recommend taking a tour here if at all possible–it truly adds so much context.

This tour of the Doge’s Palace + St. Mark’s Basilica is very popular and a great option!

Piazza San Marco in Venice
Stroll through Venice’s beautiful sestieri.

Venice is divided into six districts, or sestieri, and each sestiere has its own distinct flavor and beauty.

San Marco and San Polo are the most popular (read: crowded), and while they are absolutely gorgeous, we recommend making time for a walk through some of the others as well.

Castello, Cannaregio, Dorsoduro, and San Croce all have a lot of beauty, canals, and quiet streets to offer.

kate storm and ranger storm on a quiet street in venice july
Hit the water and enjoy Venice’s canals.

While the gondolas are (deservedly) famous, there are indeed ways to experience Venice’s canals on any budget.

Whether you want to splurge on a private gondola ride, opt for the mid-range shared gondola option, or stick to a budget and tour the Grand Canal via Vaporetto, there’s a canal option open to you!

Our guide to gondola rides in Venice will help you know what to expect, or, if you want to find a way to enjoy a gondola ride for just 2 Euro (not a typo!), here’s how to find a traghetto.

Venice Grand Canal with gondola paddling across it--a must-see item for your 2 week Italy itinerary!

Things to Consider When Visiting Venice

Especially if you’re visiting during the summer, Venice will be both crowded and expensive.

It’s still absolutely worth it to go, but like in Rome, consider early wake-up calls to get the most out of your experience.

What to Do in Venice at Night: 9 Fun Ideas

Some of our best memories of Venice are of walking through the city before the shops even start opening–and we’ve often found that we get our best photos of Venice then, too.

Keep in mind that if you want to take an iconic gondola ride, you’ll be paying a pretty penny–80 Euro/gondola worth.

After enjoying more than one gondola ride in Venice, we can confirm that they are worth it to the right traveler–but you can absolutely have a fabulous trip to Venice without one, too.

kate storm and ranger storm in a traghetto gondola during summer in venice italy

Where to Stay in Venice


Hotel Casa Boccassini — This cute hotel easily met our needs during our first trip to Venice!

The room was simple but clean, and the shared bathroom was a fair trade in exchange for their competitive prices in a great location in Cannaregio.

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The bathroom was clean and we had a sink in our room, both of which always make shared bathroom situations much easier.

The courtyard of the hotel was beautiful!

The hotel was a simple and beautiful 10-minute walk from the Rialto Bridge and just a 5-minute walk from the Vaporetto to the airport.

Check rates & book your stay at Hotel Casa Boccassini!
Couple in front of Bridge of Sighs in Venice

Hotel Lisbona — We decided to check into Hotel Lisbona for one reason: we wanted to stay on a canal!

If you’re looking to stay right on a canal in Venice without paying luxury prices, we can heartily recommend Hotel Lisbona.

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The building is beautiful and definitely has that oh-wow-I’m-in-Venice effect (especially when you look out the windows), the customer service is great, and the included breakfast is tasty.

The central location (it’s around a 5-minute walk to Piazza San Marco) couldn’t be better.

The downside? The room we stayed in was tiny–but to be staying right on a Venetian canal in such an amazing location, we definitely considered the trade-off worth it.

Check rates & book your stay at Hotel Lisbona!
kate storm looking out the window of Hotel Lisbona, recommended hotel for 2 days in Venice
The view from our room at Hotel Lisbona–not a bad place to wake up in the morning!

Hotel Danieli — If you’re looking for a true luxury experience for your 2 days in Venice–the kind of hotel stay that you’ll remember for the rest of your life–look no further than the iconic Hotel Danieli, located inside 3 former palazzos along the Riva degli Schiavoni.

Every detail has been looked after here, and everything from the furniture to the breakfast to the location (mere steps from the Bridge of Sighs) to the truly stunning lobby will ensure you have an absolutely unforgettable trip to Venice.

Even if you don’t check in, consider dropping by the bar to see the beautiful lobby for yourself!

Check rates & book your stay at Hotel Danieli!
Lobby and staircase of Hotel Danieli in Venice--the perfect luxury hotel when deciding where to stay in Venice!
Isn’t the lobby of Hotel Danieli just gorgeous? No wonder it starred in a Bond movie!

More (Or Less) Than 2 Weeks in Italy?

Italy has an endless amount of places to see, and no 2 weeks in Italy itinerary could dream of covering the whole country.

If you’re visiting over the summer (or over the winter and you like to ski) and find yourself with more time in Italy, consider heading to the South Tyrol region to experience the Dolomites (also known as the Italian Alps).

101 Important Travel Tips for Italy

You could also head to Lake Como and stop off at Milan along the way, or stay further east after leaving Venice and hit up the stunning Verona.

Bologna, which is known as one of Italy’s great foodie cities, is another wonderful choice, and also includes the option of a day trip to the microstate of San Marino.

And, while Bologna is the most famous place to visit in Emilia-Romagna, we’d be remiss not to point out Ravenna (home to absolutely incredible UNESCO-recognized mosaics) and Parma (the origin of parmigiano-reggiano and a delightful city) as well.

kate storm visiting parma italy with baptistery in the background and red vespa in the foreground

South of Rome, you could head to the incredible Amalfi Coast or the stunning island of Capri, and stop off for a day along the way to eat pizza in Naples.

Further south, the stunning beaches and towns of Puglia make for a memorable summer trip to Italy.

17 of the Best Coastal + Beach Towns in Italy

Even with all that, you’re still barely scratching the surface of Italy (and of course, every single one of the destinations included in this 2 week Italy itinerary could easily take up more time as well)–but that’s ultimately a good thing.

If there’s one thing that we’re certain of after more than a year of exploring, it’s that there is always a reason to plan another vacation in Italy.

2 Weeks in Italy Itinerary: San Gimignano, Tuscany

With One Week in Italy

If you only have roughly one week to spend in Italy, we–heartbreaking though it is–recommend cutting at least one of the destinations suggested on this 2 week Italy itinerary. 

Personally, we’d first cut Cinque Terre (especially if you’re visiting outside the summer season), leaving the trifecta of Rome-Florence-Venice intact.

We go into this further in our guide to spending a week in Italy, as well as provide other suggestions on how to make the most of a short Italy itinerary.

Northern Italy vs Southern Italy: Which Should You Visit?

If you need to cut a second destination, let geography be your guide, and trim off whichever destination will take the most time to reach based on your travel plans.

I know it’s incredibly hard to cut destinations, but rushing to a new place almost every day will eat up way too much time that should be spent experiencing Italy.

And ultimately, any given two, or even one, of the destinations covered in this Italy itinerary, could make for a magnificent trip.

Couple in Soprabolzano

With 3 Weeks in Italy

If you have an extra week to tack onto this 2 week Italy itinerary, lucky you!

You’re in for a real treat with a whole 3 weeks in Italy.

Our personal recommendation would be to use that extra week to add on Naples, Pompeii, and the Amalfi Coast.

Kate Storm and Jeremy Storm on a balcony overlooking Positano

If you’re a fast-paced traveler, you could cover those destinations in 4-5 days and spend the remaining time sampling Milan and Lake Como (the town of Bellagio is just as picturesque as the pictures imply).

With that, you’ll cover the vast majority of the country’s best-known sights on your trip to Italy!

How to Order Coffee in Italy: Essential Guide for Caffeine Lovers

Alternatively, if you’re more of a slow, immersive traveler, use the extra week to really dig into one of the regions already included on this Italy itinerary.

Tuscany or Rome would be our pick (and you can technically take a very long day trip to Pompeii or Naples from Rome if you want to try to get the best of both worlds).

Photo of the cliffs of Capri

Getting Around Italy

Within each of the destinations outlined in this 2 weeks in Italy itinerary, walking will likely be your most common method of getting around, and also half the fun of traveling Italy!

You’ll probably want to mix in some public transportation as well, particularly in Rome, but strolling through destinations like Venice and Florence is by far the best way to explore them.

Getting between destinations, however, is a different story–here’s a quick outline of transportation within Italy.

Frecciarosa Train in Italy: Florence to Bologna Train


Trains rule on-the-ground travel in Italy: if you’re not going to rent a car, it’s likely you’ll be getting around Italy by train.

Every train we have taken in Italy has been comfortable and pleasant, but keep in mind that strikes can occasionally interfere with travel.

We definitely recommend booking your train tickets in advance if you’re traveling on Italy’s high-speed trains, as these tickets can increase in price as the dates get closer.

If you’re traveling on the regional train, you don’t need to worry about booking ahead, as the prices are fixed. 

We typically travel Italy by train with Trenitalia, Italy’s national company, but Italo (a private company) is also excellent for some routes.

trentitalia high speed train in milano centrale station, as seen when traveling italy by train

In Lombardy (where Milan and Lake Como are located), you’ll also see Trenord-branded trains.

You can check prices and compare rates, schedules, and more on Omio to ensure you’re getting the best deal on train (or bus) travel in Italy.

We use Omio regularly throughout Europe and have always had good experiences with it.

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If you do happen to buy a train ticket at the station (for a day trip, perhaps), keep in mind that paper train tickets must be validated before boarding the train in Italy, and failing to do so could result in a hefty fine, being thrown off the train at the next stop, and an enormous headache.

As far as we’re concerned, that’s another reason to book online, as showing the tickets on your phone to the conductor is just fine.

Shop train tickets for your 2 week Italy trip today!

Honeymoon in Tuscany: Views of Tuscan Countryside


Renting a car to drive through Italy is a popular option, especially in places like Tuscany, but there are a few things you’ll want to consider before you do.

Keep in mind that cars are restricted from driving into the historical centers of most cities, including Florence and Venice, and failure to adhere to these rules (even accidentally) can result in strict fines that you sometimes find out about through the mail months after the fact (my dad and a good friend have both been fined for driving in Italy via a summons after returning home).

7 Phenomenal Italy Road Trip Ideas (+ Driving Tips!)

For that reason, as well as issues with extremely limited parking in cities, we recommend limiting car rental when possible to time spent in smaller villages and towns.

While we love taking road trips in Italy, this itinerary for 14 days in Italy doesn’t require one, with the possible exception of renting a car for a couple of days to explore smaller villages in Tuscany.

If you do want to rent a car in Tuscany, know that an international driver’s permit is required for renting a car in Italy and must be obtained in your home country before arriving.

Siena Day Trip: Jeremy with Classic Cars

Sometimes car rental companies ask for it, sometimes they don’t (same with the police), but in our opinion, it’s not worth taking the risk–add this to your list of things to take care of being starting your 2 week Italy trip if you plan on renting a car.

Also, keep insurance in mind!

Thanks to Italy’s (somewhat deserved) reputation for less-than-cautious drivers, some travel insurance companies will not cover you while driving in Italy, or charge an extra fee to do so. Be sure to double-check before you book.

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If renting a car is the right choice for you, we recommend browsing Discover Cars, and aggregate for finding rental cars in Europe (and beyond, though they’re most popular in Europe).

Discover Cars will search both local and international brands that have available cars for your dates, and allow you to compare prices, reviews, and inclusions side-by-side.

Shop rental cars for your Italy vacation today!

Quiet street in Venice, to be visited on this 2 week Italy itinerary


Bus travel in Italy is much less common than in some other European countries, mostly because of their well-developed train system.

44 Villages + Small Towns in Italy That Are Worth a Detour

You can find some buses available, however, especially among smaller cities and villages (we’ve used local buses in South Tyrol several times), as well as throughout certain parts of southern Italy.

If you’re having trouble deciding how to get around a certain destination.

In addition to trains, you can also browse some long-distance buses via Omio.

kate storm and ranger storm in front of the pantheon when visiting rome italy


If you’re hoping to be careful of your budget during your 2 week Italy trip, we recommend looking into flights for the Rome to Venice (or vice versa) leg of this itinerary.

Trains are a comfortable, romantic, and easy way to travel, and they also often cost more than budget flights do!

2 Weeks in Italy Itinerary

When to Visit Italy for 2 Weeks

There’s no such thing as a bad time to spend 2 weeks in Italy, but some seasons are definitely more convenient to travel in than others.

Summer is the most popular season and will bring warm weather, lots of sunshine, and lots of tourists.

Prices will be at their highest, but the beaches will be at their best–if you’re hoping to swim at Cinque Terre, you’ll want to plan a summer trip.

What to Buy in Italy: 35+ Best Italy Souvenirs

Winter is the offseason and will bring colder temperatures, rain, and gray skies.

Prices will be at their lowest, and crowds will be as small as they ever get.

The Christmas season can bring increased crowds, but also the benefit of experiencing Christmas decor and markets (though fair warning–these have nothing on the Christmas markets in Austria and Germany! Check out Bolzano for something close.).

jeremy storm and ranger storm in front of milan christmas tree galleria vittorio emanuele
Christmas in Milan!

Personally, our favorite times to travel to Italy are the spring and especially the fall.

The crowds are less than in the summer, spring brings beautiful blooms, and fall brings the olive harvest (after tasting fresh olive oil in Tuscany, I don’t know how we ever lived without it).

17 Wildly Romantic Places in Italy

The weather is a bit riskier during the spring and fall than during the summer, but we have never had much of an issue with it.

The occasional rainy or cool day is worth it to us for the tradeoff of not being hot and crowded, and October is our personal favorite month to visit Italy.

Ultimately, though, whenever you have a chance to plan a 14 day Italy trip, take advantage of it: every month of the year brings distinct upsides and challenges, but each and every one of them is worth the trade-off.

2 Weeks in Italy Itinerary: View of Siena

What to Pack for Italy

Planning a packing list for 2 weeks in Italy can be a challenge of its own!

We have a full Italy packing list here, but to get you started here are a few things to be sure to bring on your trip to Italy.

Travel Adaptors for Italy — If you’re coming from outside of Europe, you’ll definitely need adaptors for your electronics.

33 Best Books About Italy: A Literary Guide

Pacsafe — We can’t recommend our Pacsafe enough: this travel safe is affordable, sturdy, easy to pack, and will help keep your valuables safe in your hotel room (not that you should need to worry much about theft in Italy, but it’s better to be safe than sorry!).

Money Belt — This is up to you: we no longer use a money belt, but if you’re more comfortable having your passports on your person in Italy, you can consider bringing one. We used to use this one and had no complaints.

These days, we prefer just to leave valuables in our Pacsafe during the day.

2 aperol spritzes being held up in lucca, a fun stop during a 14 days in italy itinerary

Umbrella — Option A: Plan on buying an umbrella when it starts pouring down rain. Option B: Plan ahead and buy a (probably much sturdier) umbrella before leaving.

Option C: Hope you get lucky with the weather (but fair warning, we’ve never been avoided rain entirely during a trip to Italy!).

Small Pack of Tissues — Most bathrooms in Italy will have toilet paper, but not all of them (especially in smaller train stations).

Bring a small pack of tissues, toss them in your day bag, and you won’t have to worry about it.

Purell Hand Sanitizer — We’ve never been sorry to have this floating around in our day bag.

kate storm and ranger storm on a cobblestone street in castell arquato italy

Travel Journal — If you want to keep a travel journal, but can’t commit to a huge amount of writing each night, I recommend the One Line a Day Journal.

I’ve been using it for more than 5 years now and am now working on my second volume, and I absolutely adore it!

Italian Breakfast Guide: How to Enjoy Breakfast in Italy

Sea Bands & Non-Drowsy Dramamine — If you’re prone to motion sickness like me, I strongly recommend adding Sea Bands to your Italy packing list.

I use them on all boats and the occasional bus, and if things get really bad, take some Non-Drowsy Dramamine as well.

Before heading off for your 2 weeks in Italy, be sure to read through our complete Italy packing list!

Your 2 Week Italy Itinerary Map

Take This Map With You! Click each highlight to pull up the name of the destination. To save this map to “Your Places” on Google Maps, click the star to the right of the title. You’ll then be able to find it under the Maps tab of your Google Maps account! To open the map in a new window, click the button on the top right of the map.

2 Weeks in Italy Itinerary: #rome #florence #tuscany #cinqueterre #venice #italy #travel

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About Kate Storm
Image of the author, Kate Storm

In May 2016, I left my suburban life in the USA and became a full-time traveler. Since then, I have visited 50+ countries on 5 continents and lived in Portugal, developing a special love of traveling in Europe (especially Italy) along the way. Today, along with my husband Jeremy and dog Ranger, I’m working toward my eventual goal of splitting my life between Europe and the USA.

148 thoughts on “How to Spend 2 Weeks in Italy (Itinerary for 14 Perfect Days!)”

  1. I’m in Veneto, and so am biased about what I write about Italy. You covered some great places like CInque Terre and beautiful Toscana. I totally agree about heading to see the Alps, the Dolomiti is a must too. Beautiful photos to accompany the post too!

    • I went in October 1-14, 2021, we had one evening of rain in Venice but we went to a concerto and the rain was over when we came out of the concert!!! I had the best trip ever!!!!!! My daughter planned it and she did an excellent job, Naples to Rome to Florence to Tuscany to Venice to Cortina to Venice train to Naples to Mt. Vesuvius to Pompeii to Verti to Amalfi Coast. It was an amazing trip and I want to go back too.

  2. A great article for first timer to Italy. I have sent this to my partner and I hope he reads it, I have dreamed of coming to Italy since I was a young girl. My parents went to Italy and always spoke of Venice and Muranos Island and of course glassware. Your photos are spectacular.

  3. Italy is such a cool destination and this is the perfect guide to plan a trip in two weeks. I have been to Rome once and your pictures of Trivi Fountain is amazing as during my visit it was mainly crowded. Did you explore the islands near Venice too ?

    • No chance to go to the islands, sadly–the weather didn’t cooperate with us too well in Venice. Hopefully next time! We’d especially love to go to Burano.

  4. I was actually wondering where you were off next, after reading your Rome post 🙂 although not a big fan of Italy overall, I am a huge fan of Tuscany… I only got to spend 2 days in Florence a few years back, so it is definitely on my travel list! Love your pics!

  5. I visited Italy for the first time last year, travelling to Rome and it was magical. The amount of culture is unbelievable, I would love to travel to Florence or Naples next time!


  6. Your pictures are really enticing. A trip to Italy would be incomplete without taking up a culinary class or 2 in Tuscany. Cinque Terre looks particularly interesting too. Will get back to you for travel-planning. 🙂 Cheers!!

    • You’re totally right, Aditi–our cooking class in Tuscany was one of our highlights of our month there this year! Food in general is such a big part of traveling in Italy, it really adds something to the whole experience.

  7. I agree with you that one cant get enough of Italy…and this time I really mean it! So much cosy villages and site to explore…and not to mention the food! I have been to Italy many times before living in the country next to so I think you have chosen a great destinations for a two weeks itinerary for a first-timer! I hope to visit the northern and souther part of Italy this summer!

    • Oh, it must be so much fun to live in Italy! I’m sure it comes with its challenges as well, like any destination, but if we could pick somewhere to live for a year, Italy would be VERY high on the list!

  8. Eat, Pray, love put Italy on my map. And, I am so glad it did. I really enjoyed my time in Italy. And, without knowing I almost followed your first-time visitor itinerary. The country is so beautiful that one time is not enough. I am aching to go back. Maybe this year it will happen.

  9. A nice itinerary that you have suggested. Did all these except for cinque Terre. Wish someone had advised me then to do that. I hope to go back to Italy again to see this. Cheers

  10. Hi Kate,

    Curious, how did you decide the order of your destinations? We’re doing 15 days in Italy and flying into Rome. We’re trying to visit Venice, Florence, Cinque Terre, Tuscany then Amalfi Coast before returning to Rome for our flight home. Any advice on the best order?


    • Hi James!

      We actually put this itinerary together based on a couple of months worth of travel in Italy, so we didn’t follow these steps exactly in order (though we’ve visited all of these destinations, some more than once!).For your trip, assuming you’re flying out of Rome as well, I’d personally probably structure it as: Rome to Cinque Terre, Cinque Terre to Florence/Tuscany, Florence/Tuscany to Venice, and Venice to the Amalfi Coast (you’ll need to stop by Rome again) before returning home.

      No matter what way you do it, you’re going to have a lot of travel time in there–you’re covering quite a bit of the country.Honestly, I’m tempted to say you should skip either Cinque Terre or the Amalfi Coast (the Amalfi Coast would make more sense to cut geographically, hence why it didn’t make this itinerary) and slow the pace a bit, but I know that’s much easier said than done–when you have a limited number of days, you want to see it all!

      Not sure how you’re planning on getting around, but I’d consider saving some time and flying from Venice back to Rome–budget airlines (including Ryanair) fly in/out of both those cities, and if you plan in advance, you may be able to get very low fares. Also consider booking any train tickets you need in advance–fares go up dramatically the closer your dates get.

      Hope you guys have an amazing trip! Italy is absolutely incredible. ?

  11. Hi Jeremy and Kate,
    Warm greetings from India. I discovered your blogsite recently and this is really amazing 🙂
    I wanted a favor from you guys, I will be travelling to Italy soon, for some office work in mid march. I will stay at Siena for 14 days. Can you please please please recommend me a travel plan or at least help me with details of rail travel?
    I intend to see Rome on one weekend, Venice and Milan on other weekend. I intend to travel Florence and Pisa during weekdays, when we get time off.
    I wish to hear from you guys…
    Love from India <3

    • Hi, Akshay! That’s not a service that we offer, but I can say that we used Trenitalia for our train tickets and were very satisfied with them. I recommend booking as soon as you know your dates, because prices do get more expensive over time. I think seeing Venice and Milan in a single weekend will likely be too much–unless you’re dying to see Milan in particular, I’d recommend skipping it and heading right to Venice. Good luck!! Hope you have an incredible trip.

  12. We leave for our first Italy trip next week! I am so excited! When we were first planning our trip we were trying to pack too much into 14 days. We settled on flying into Venice for two days, heading to Modena for two days, traveling to the Umbria region for 5 and ending in Rome where we fly out.

    • Oh, that is so exciting! It’s definitely tempting to try to stuff too many destinations into too few days, but your trip sounds wonderful. I hope it helps you fall in love with Italy!!

  13. Hello- We are traveling to Italy for first time in August 2018. Flying in to Venice and staying for 3 nights. Then to Florence for 4 nights, and on to Rome for 6. Flying back to US from Rome. Question– Should we decrease time in Rome to add 1-2 nights in Naples or Sorrento to see Amalfi Coast? We will do day trip from Rome –> Naples –> Pompeii, but just curious if we should try to squeeze in Amalfi Coast. Thank you!

    • Hi Vicki! It’s hard to say without knowing your general travel style (how badly do you want to see the beach?), but our recommendation would be to stick with Rome for 6 nights, or to add on an additional night onto Florence and potentially use that as a day trip to Cinque Terre (you’ll need a car to do that, but it’s a shorter drive than Rome –> Sorrento). Good luck with your planning–your trip sounds fabulous!

      • Thanks so much Kate! The attraction to Amalfi Coast is b/c we have heard how beautiful it is- but it does does sound far for a day trip from Rome. I keep reading about Cinque Terre but we are not big hikers (knee issues…!). Would Cinque Terre be worth a day trip (train?) on the way to Florence from Venice? Thank you so much for your help! Vicki

        • A day in Cinque Terre on the way to Florence, perhaps… but you’d need a whole day, and likely need to spend a night. There’s no direct train from Florence to Levanto (the larger village near the Cinque Terre villages), unfortunately, so traveling by train between the two without a car is harder than it appears looking at a map. Travel from Venice to Cinque Terre will likely take an entire day as well, but you could add one Cinque Terre day in between two travel days if you’d like! 🙂

          • Kate, Thank you so much– this has been enormously helpful!
            I think we’ve decided to take the train from Venice to Florence, spend 4 full days in Florence and just explore that beautiful area. We know we need at least two full days in Florence, but welcome any/all suggestions about surrounding area day trips. Grazie!!

          • Hi Vicki! Some of our favorite Florence towns include San Gimignano, Volterra, and Lucca–all great day trips. 🙂 Siena is also popular. If you have a car, there are natural hot springs in Tuscany that are supposed to be beautiful, but we haven’t made it there ourselves yet. Our “Romantic Things to Do in Tuscany” post has some great ideas as well–you don’t necessarily need to be traveling with a partner for them, either! 😉

    • Vicki- who are you booking with. This is the exact trip myhusband wants but couldn’t find it.
      flying to venice for 3 nights, florence for 4 nights, then Rome.

      • I’m not sure what Vicki is planning, but if you guys are planning the trip yourselves, I’d fly to Venice, take the train to Florence, and then the train to Rome before flying home. I’m not sure of any group tours that follow that route, though I’m sure they exist!

          • Hi Juan!

            It’s up to you and how the flights work to/from your destination.

            In a perfect world, it’s easiest to fly into Rome and out of Venice.

            However, if flights are much more expensive that way vs booking a round trip ticket, you can also take the high-speed train from Venice back to Rome to fly out. The fastest trains on that route take just under 4 hours, but you’d need to book those tickets in advance.

  14. This post is a great guide for traveling through Italy. My friends and I traveled to Italy on a rented car and visited some of these places. I advise everyone to visit here!

  15. Parking can also be a challenge around the villages–if possible, we’d recommend relying on the train or Cinque Terre’s famous trail to get between the villages. And it is very good, because in Ukraine it is big problem!^(

    • Yes, absolutely, but it can be convenient to drive to La Spezia and take the train into the 5 villages from there. 🙂 Easier than taking the train all the way from Florence for sure!

  16. This is amazing blog! My husband and I are traveling to Italy for our honeymoon in June. Could you guys shed some light on car rental and driving in Italy? Is it driver friendly with interpretable directions? My husband wants to bring a GPS – is this too ridiculous? Thank you!! Also, have you been to Capri?

    • Hey Natalie! Congrats on your wedding–we got married 5 years ago this June. 🙂 🙂 Italy is reasonably simple to drive in when you consider the quality of the roads (decent) and navigation (decent). That being said, drivers are aggressive and driving in cities is a headache–at the very least, I’d ditch the car in major cities. Depending on your itinerary, I doubt you’ll need a car for your whole trip–I’d consider where it would be more of a hindrance than a help (basically any large city and any surrounding smaller cities/towns that you can connect to by train) and go from there.

  17. I am so happy I came across your blog! We leave 9/8/18 from California and arrive in Rome on Sun. 9/9 @ 6pm My initial thought was to take the fast train to Venice on Mon. 9/10 and then work our way down to Florence, CT, Rome.. but now i am wondering if i should fly to Venice on 9/10 after a good nights rest instead of train to save time.. its the same price! Or do you suggest head straight to CT from Rome, then on to Florence, Venice and fly back to Rome to finish our trip there?? I saw you suggested above to go to CT from Rome..

    I am trying to not overwhelm ourselves as i really don’t want to spend all my time on a train or stressed out.. But i feel like these are the 4 places we want to see this time around.. (i had to talk myself out of Amalfi, Lake Garda, etc.!.. i want to see it all!) Also, this will be our honeymoon! We will be there for a total of 13 nights.

    • Hey Amanda! Congrats on your upcoming wedding!!

      September is the perfect time for a honeymoon in Italy, it’s one of our favorite months here. 🙂 I definitely understand the difficulty of cutting things down, lol–there’s never enough time!

      As far as starting in Rome or Venice, it’s mostly personal preference. I wrote the itinerary this way for two reasons: 1) most people fly into Rome, and 2) If I had to choose, I think Venice makes a better last destination than first. They’re both crowded and touristy, of course, but seeing the best of Rome requires a lot of effort and activities–the Colosseum, touring the Vatican, etc.

      Venice definitely has some great sights, but you could also spend a couple of days strolling aimlessly around the city while eating endless gelatos and still come away feeling like you “saw Venice”–in other words, it’s not as demanding as Rome IMO.

      Plus… after flying all the way from California, I’m guessing you’ll be ready to see Italy once you get here, not jump on another train/plane! But ultimately, it’s your call–I don’t think either direction would be a mistake.

      I do definitely recommend flying over train travel for the Rome to Venice route, as it’ll definitely save you time–anything that saves you time and stress on a honeymoon is a good idea. 🙂

  18. Hi there, I am taking my wife for 2 weeks coming up next month. We are staying in Cortona, Italy in Tuscancy and making day excursions to Florence, Pisa and other towns within a day of Cortona. For the second week, would it be better to start off in Venice and make our way to Rome and/or Cinque Terre or do I see about a last minute cruise from Venice through the Mediterranean. Downside would be that we wouldn’t see as much of Italy. We don’t want to be on the go 24-7 but we do want to experience Italy. Your comments are appreciated!

    • Hi Jeremy,

      Both of those options sound amazing, so it’ll really just be down to personal preference!

      I don’t know the cruise itinerary, but I would imagine that the cruise will focus more on natural beauty + beaches, and a a trip to Rome would be more focused on history (with still a sprinkling of beaches in that week if you hit up Cinque Terre).

      If this is your first trip to Italy, I personally would forgo the cruise to focus on Italy itself, but there is definitely no right or wrong answer to that!

  19. Hi, Kate,

    Great advice and itineraries, thanks so much! We’re planning an 8-10 day trip to Italy during the last 2 weeks of August and are thinking Venice, Florence and Rome (not necessarily in that order). I’m wondering if it would be a better plan to split the time between Venice and Florence and plan to see Rome during a trip during a shoulder season (we also have 2 weeks available to travel after Christmas ). Your thoughts on whether to cut the itinerary to 2 vs 3 cities during the hotter “touristy” time of year? Thanks!

    • That’s a tough question! Knowing you have another opportunity to travel after Christmas, I would probably lean toward cutting one city and sticking to two–it’ll be a more relaxing trip that way, and there’s more than enough to do in any two of those cities to keep you entertained for 8-10 days. I know it’s a hard call, though!

  20. Hello, it was nice reading your and other people’s ideas. We are going to be 71 and 72 this coming April-May when I am planning our trip to Italy. I have been before and love the trains and agree with all. But, dealing with luggage on trains is not the easiest especially as we get older. I need to book lodging before the flights and we have enough miles. If we take the train, are there taxis at all the stations to get us and luggage to where we stay? And, any idea how much or if they take credit cards like I know they do in NYC? He suggested driving for that reason, but I think finding parking with the lodging, or at the sights, would be the worse problem. Do you agree? I was thinking of mid May, but have read that May is pricey. Do you think late April is warm? I don’t want to lug jackets. My idea for 2 weeks: fly to Rome, 3 days; to Assisi, Perugio, Siena- find a place in either area for a day or 2; Florence, 3 days;Pisa 1 day; Cinque Terre/LaSpezia, 2 days; Venice -maybe drive thru Verona, 2 days.

    • Hi Roberta! Yes, I can definitely see how the luggage on and off trains can be difficult. There are taxis at most of the stations, but they don’t tend to take credit cards. Uber is available in Rome, but no other city on your itinerary. I would say that driving is definitely more trouble than it is worth for larger cities like Florence, Rome, and Venice–you could consider driving to Cinque Terre, but you’ll likely just be leaving the car at the hotel the whole time.

      I’m not sure what your budget is, but some hotels will also offer an airport (and possibly train station?) pick up service–for a fee, of course, but they would be able to help with the luggage.

      Late April is a bit unpredictable with the weather–it may already be getting warm in Rome, but Venice will almost certainly still be jacket weather. You never know, though! We were in central Italy during late April this year (Bologna/Emila-Romagna) and we still wanted light jackets until around the beginning of May.

      Hope this helps! 🙂

  21. Hey! Came across your blog and this is super helpful. Even reading through all the comments.

    My wife and I are flying into and out of Rome in September and have 14 days in Italy. We were thinking after arriving in Rome hopping on a train to Venice and staying there for about 3 and a half days then taking the high speed train to Naples and spending some time in Sorrento and that area for about 4 days and ending in a Rome for about 4-5 days. I’m not counting the days where it’s mostly traveling.

    Do you think this is feasible? Should we add a city worth seeing or is it too spread out to really enjoy it? We want to make the best of it since we may not get back there soon but I also don’t want us running around so much that it becomes in enjoyable.

    I appreciate your feedback!

    • Hey David!

      It is feasible! You’ll be tired, but it looks like you have enough time to work with. If you have your heart set on those destinations, I’d look at a budget flight instead of a train for Rome/Venice and back–round trip fares can be quite inexpensive on discount airlines like Ryanair, and I know they have lots of flights between both cities.

      With a 14 day trip, I would personally be tempted to trim a day from each of those destinations and add in another city (Florence/Tuscany would be my personal first pick), but you certainly don’t need to, and you guys know your pace best.

      If you’re 100% sure on dates, I’d check on flight and train prices *now*–the high-speed trains that go between multiple regions of Italy (ie, the Rome–>Venice and Venice–>Naples trains) can be pricey, and the prices do increase as the dates get closer. With regional trains that stay in one area (just Lazio or just Veneto, for example), the prices are fixed and you can just buy whenever. 🙂

      Have fun!! September is a magical time to be in Italy, I’m sure your trip will be wonderful.

  22. Hi
    I Loved your itinerary, am thinking of something similar in October for my family.
    Could I ask what your final budget was for travel and accommodation / tickets etc please?
    Many thanks Carly

    • Hi Carly!

      We put this itinerary together based on several months traveling in Italy, so it’s hard to extrapolate out what we would have spent. Speaking generally, I would say 140 Euros/couple/day, adding additional funds for kids, is a comfortable midrange budget in Italy, though you can easily do it on a far smaller or far bigger budget as well. If you plan to rent a car in Italy, that will eat into costs and you may want to budget extra for that.

  23. Hello
    I am in the process of planning a summer trip to Italy with our kids. We are flying into Venice ( award travel) and was planning to stay 2 nights, then stay 5 nights in Tuscany and then head to Positano for 5 nights. Will fly home from Naples or Rome. On our first trip to Italy we did Florence, Cinque and Rome. I was dreaming of a farmhouse/villa stay in Tuscany but so far they are all a Saturday to Saturday stay. We arrive in Venice on a Monday and was planning Tuscany for a Wednesday arrival for 5 nights. Wondering if we should skip Positano and go somewhere for 5 nights before Tuscany? Or should we fly from Venice to Naples , visit Amalfi area and then head back to Tuscany? Or maybe you know a place that doesn’t require a week stay in Tuscany? Is there a Tuscan town you recommend for a good home base? Trying to make the best use of our time. I am getting confused 🙂 Our kids are teens.
    Appreciate your thoughts!

    • Hi Sally! It all depends on what you’re looking for–Positano is beautiful, but if you’d rather stick to a closer geographic area, Verona and Emilia-Romagna (possibly based in Verona) would be good options between the two. For beaches, there’s always Elba in Tuscany (though that can be a little harder to get to). I don’t know of any Tuscan villas offhand that aren’t only Saturday-Saturday, but I would guess that VRBO and maybe Airbnb would be your best bets for that. We use VRBO for our multi-generational family trips to Tuscany. 🙂 Tuscany is one of our favorite places, so I’d have a hard time saying you can go wrong with a base there! Siena and Lucca are both great options if you’re wanting something smaller than Florence, but you’ll definitely need a car for day trips if you’re wanting to explore the region (and especially if you’re staying outside the city center).

  24. I enjoyed reading your blogs very much. My family and i will have only 5 days in Italy, as a side trip from Germany. Where would you recommend that we must visit, as a first timer to Italy? Also, are there flights/trains that go directly to Florence?

    • Ahh, that’s a hard one! The answer is, of course, wherever you are most invested in going–but in my personal opinion, I’d pick Tuscany. It’s easy to navigate, incredibly beautiful, and very classically “Italian” for first-time visitors. It’s also one of our favorite places in the world, so I’m a bit biased. 🙂 There are flights and trains that go directly to Florence, but on that timeline and coming all the way from Germany, I’d definitely fly. If you’re open to budget airlines, be sure to check Pisa–it’s about 20-30 minutes outside of Florence, and most of the budget airlines fly there instead of directly to Florence.

  25. We are heading to Italy (first time for me) next fall with 2 other couples and are just now starting to research. Your blog is amazing and really is helping us formulate our trip. Have you ever cruised the coast of Italy ( i want to see as much as possible going for 2 weeks) and know we cant see it all but wondered how a cruise (small less then 300 people) might help us see all those amazing sights on the water – 7 day then heading into shore and seeing the other parts of Italy.

    • Hi Barbi!

      We haven’t had the chance to cruise the coast of Italy (yet), but it’s actually on our list of Italy trips we hope to take one day.

      If your goal is to see as much as of Italy as possible, I would say the benefits of the cruise depend on where exactly it goes and what your priorities are. I’d check and see how much land time there is vs cruising time, etc. It’ll definitely cut into your time in Italy itself, but it would also undoubtedly be a beautiful and unforgettable experience in its own right. The coast of Italy is incredibly gorgeous!

  26. Did you take the picture of the Tuscan countryside that is right before the “Cars” section of this blog? If so, where is that at?

    • Yes we did!

      It was taken at a winery outside of San Gimignano–those are the towers of San Gimignano that you can see in the far distance. Unfortunately, I didn’t note the name of the winery at the time, but there are similar views all throughout the area!

  27. Kate,
    My husband and I are planning to go back to Italy next October.our past trips were Florence, Tuscany and a Rome. This time we’re going to Umbria area and the Amalfi coast probably 14 days total. My question is what order do you suggest? Last trip we felt like we should have done Rome first then Tuscany, Rome was hustle bustle and Tuscany was laid back and relaxing..we felt we should have stayed in Tuscany last. What place would you suggest starting and ending with.

    • Hi Micki!

      If you’re looking to start with hustle and bustle and then end with somewhere relaxing, I’d recommend starting with the Amalfi Coast and then heading onto Umbria! As a bonus, you’ll then be near the coast a tiny bit earlier in the season, so hopefully some of the warm weather will hold out for you (and it very well might–we’re in Rome right now, and even though we’re into the second half of October, it’s 80F and sunny out!).

  28. Hi, Thank you for sharing this itinerary – so helpful as we have never travelled to Italy and are planning our first trip later this year. We would also like to visit Pompeii. How long would you spend there and where would you stay to include this stop. Thanks so much

    • Hi Janine!

      I’m actually working on a Pompeii/Mount Vesuvius guide that should be published sometime this month, so be sure to check back for more detail, but here’s the short version–it depends on how much time you have.

      If you only have right around 2 weeks in Italy and don’t want to cut any other destinations, you can do Pompeii as a day trip from Rome. However, the only way to feasibly do that well (especially on a first trip to Italy) is to book an all-day tour, and it’s about 6 hours of driving roundtrip.

      Alternatively, you can stay in Naples and visit independently. Naples feels very different from the rest of this Italy itinerary, which focuses on north and central Italy instead of the south of the country, but it is a lovely city with some fascinating things to do, the world’s best pizza, and easy access to Pompeii. It’s considered “dirty” by many, but it doesn’t personally bother us a bit, and we don’t think time there is wasted.

      For Pompeii itself, you really only need one day, and with some solid planning, a base in Naples, and an alarm clock, you can squeeze in a visit to the crater of Mount Vesuvius or Herculaneum that day as well.

      If you wanted to visit via Naples and keep most of this itinerary structure, add on a stop after Rome. You could then double back to Cinque Terre or simply swap Cinque Terre for the Amalfi Coast, which is very close to Pompeii and Naples, before heading up to Florence + Venice.

  29. Hi. I am visiting Italy in April and would like to go to the Dolomites. I will be staying at Peschiera del Garda for 5 nights. Will I be able to visit the Dolomites from this place? Will Dolomites be accessible in early May?

    • Hi Sheena!

      We haven’t been to Peschiera del Garda, but there are plenty of day trips to the Dolomites sold that leave from there, so you should be safe. 🙂 The Dolomites are pretty accessible–depending on altitude you may still see some snow in early May and certainly some colder temperatures, but you should be able to access the mountains to experience some beautiful views (I’m assuming you’re not planning on doing any intense hiking since you’re basing yourself near Lake Como).

  30. Hi! I am trying to plan a trip to Italy for May. We want to go to Venice, but have also heard that there are new laws for tourists and how expensive it is during this time of year. I know it is so overly visited by tourists, and just wanted to ask you if you think it is worth it. It would be at the end of our trip, and only 2 days. If not, we may stay south. Thanks!

    • It’s an interesting question, Hannah. We’ve personally only visited Venice in the late fall, so we haven’t experienced the summer crowds ourselves–but we know they are intense.

      If you have always wanted to see Venice, I do think it’s worth it–no matter how many cities call themselves “the Venice of X place”, there truly is only one Venice. It’s an incredibly unique and beautiful city.

      However, you will definitely pay for the privilege–it’s expensive, and there will be crowds in May, especially if you go toward the end of the month.

      I’d recommend pricing out hotels and activities for your dates, adding up the estimated cost, and asking if you think that number–including the cost of getting to/from Venice–is justified based on how much you want to see it.

      If you don’t mind crowds, have always wanted to see the city, and don’t mind the cost (much)–go.

      If you’d prefer to visit somewhere less congested and Venice is somewhere you’re considering visiting just because it’s an obvious choice and not because you’re excited to see it specifically, look at staying further south.

  31. This is WONDERFUL! My fiance and I are planning a two week trip to Italy from the States. Any chance you have a rough estimate on how much to budget for all of this? Thanks so much!

    • Thank you, Marissa! Plane tickets will be incredibly dependent on where you are flying from in the USA–Las Vegas, Orlando, NYC, Chicago, Atlanta, and sometimes Boston are all places to check for budget airline flights if you’re looking to save cash and those are an option for you. To help with budgeting on the ground, we put together this post:

      Hopefully that helps give you a general idea!

  32. That’s a really informative article Kate!

    I need some advice from you. I am planning to visit Italy on my honeymoon in late November. I know it’s not an ideal season for sightseeing and getting around, but would you recommend including Catania or Malta in the itinerary during that time of the year? With some quick research I noted that these locations offer warmer weather, but I never saw these places covered in any itineraries available online. Would you be aware of any reason for that?

    Thanks in advance!

    • Hi Ronit!

      Late November will really be too late in the year for any swimming, but Sicily and Malta will still be beautiful.

      Catania is not generally considered to be a great place to sightsee in Sicily–Taormina, Siracusa, and even Palermo are all more popular. We skipped Catania ourselves for this reason, so I can’t offer any personal advice there. We did love Palermo, which is Sicily’s other major airport hub.

      The best way to find itineraries for Malta would be to search for those itineraries alone–it’s not usually combined with Italy (not sure if that’s what you were searching?). It is a lovely place, and if you’re content to sightsee on land and skip some of the more summery activities, I think a November trip could be fun.

      Other than weather, etc, if you want to include either Catania or Malta in your trip, the other two things I’d check on are flights (many budget flights to/from beach destinations are seasonal and won’t be running in November), and for Malta, whether anything you want to do is closed for the season.

      Also, I’m not sure if you’re looking for a particular kind of trip, but depending on how late in November you go, you may be able to check out some Christmas markets in Italy and/or Malta, so keep an eye out for those!

      Congratulations on your marriage–hope you have a wonderful trip!

  33. Great article thank you so much! We just really don’t have interest in Venice (I know it’s weird) but would you suggest we could easily sub in Milan/Como for Venice?

    • You can! Milan and Venice can be reached in roughly the same amount of time from Florence, give or take depending on your train route. If you’re looking for other places in northern Italy to consider, you might like to take a look at Verona or Bologna as well. 🙂

  34. This is a great and detailed article to aid in starting up creating one’s itinerary! I doubt 2 weeks would be even close to being enough if I wanted to see most of Italy in one go, especially since I am dying to see Milan, Lake Garda and Amalfi Coast!

    – Laura

    • I’ve finally come to the conclusion that no amount of time is enough for Italy! I don’t think we’ll ever be done going back. 🙂 We still need to make it to Lake Garda (and Lake Como, and Lago di Braies, and Lago di Sorapis…) ourselves.

  35. Thank you for the information.
    Q: If we ignore the time to travel, cost and all other extranal factors. Which is a better place to see Cinque Terre or Amalfi Coast?

    Q: What other place in a differnt country in europe can I travel from Italy for a three day trip?

    Have a good say!!

    • Hi Joe!

      For your first question, personally we slightly prefer Cinque Terre, but it really just comes down to personal preference at that point! Both are phenomenal, neither is objectively better.

      You can go just about anywhere in Europe for 3 days from Italy, as there are budget flights from all the major cities to just about anywhere on the continent! If you are looking for something geographically close and/or you don’t want to take a plane, Slovenia, Austria, Switzerland, France, etc, are easy to reach from the north, San Marino is accessible from Emilia-Romagna and the surrounding area, and Malta, Spain, and Croatia are accessible by ferry, just to give you a few ideas!

  36. Very engaging and informative read! Enjoyed your blog. In process of planning trip to Italy in mid November. Flying in at Milan and out from Rome.
    1N(Night) Milan
    3N Dolomites
    2N Venice
    3N Cinque Terre
    3N Florence/Tuscany
    2N Rome
    2N Naples

    Love for mountains and offbeat places (less crowded) places. On a budget trip, depending on public transport.

    (1) If you can suggest base location /or (BnB or Hostel) for Dolomites and Naples
    (2) Any other location, where exploring around would not be straight forward as will be dependent on public transport
    (3) Is the itinerary good mix of days and routes? If you think by any ways can swap days / location..please do recommend

    Grazie 🙂

    • Thanks so much, Niket! That trip sounds amazing, if a little fast-paced for our tastes. 🙂

      For the Dolomites, Cortina d’Ampezzo and Bolzano are two of the “bigger” cities (and I use bigger loosely) that people use for a base. There are plenty of small towns as well, but keep in mind that in November there could be snow, etc, to contend with the higher you go, and public transportation options will be fewer and a bit more complicated.

      For Naples, the biggest thing to keep in mind is the hills! The further you stay from Piazza del Plebiscito, the more hills you’ll climb. We stayed in the budget hotel linked in this post on our first visit to Naples and liked it well enough (the nearby escalators to get down the hill definitely helped):

      As for the route, I personally would cut Cinque Terre and/or the Dolomites, as in mid-November the weather isn’t likely to be great and you have a lot of places that you’re covering. I’d be tempted to give over another night to Venice and another two nights to Rome in exchange, but that’s entirely personal preference!

      I’d also recommend not counting too much on getting to see a particular hike, etc, in the Dolomites. It’s very likely that it will be cold, rainy, and maybe even snowy by mid-November, though undoubtedly still beautiful!

  37. Thanks for the great ideas and tips. We’re a family of 4 thinking of a 2-week trip to Italy next summer and your itinerary could be a possibility (in reverse, as we’d start in Venice). Can you suggest any good self-catering or apartment rental options for the itinerary? Or trustworthy websites to try? Thank you in advance!

    • Hi Dee! Depends on what you’re looking for, size of group, etc, but for self-catering apartments we generally book through or Airbnb. For villas/large groups, we’ve found excellent properties through VRBO. We highly recommend a country villa for a couple of nights in Tuscany if it fits your group and budget!

  38. Hi Kate, very helpful blog indeed, thanks. I am struggling to work out the perfect itinerary because I need to visit Bologna for business. My plan ( which can be tweaked ) is to fly into ROME March 2 arriving 7 am and fly out March 16 at 11 am. I need to arrive Bologna 11th evening, and leave 14th evening or 15th morning. I can move my dates 1-2 days before or after. I am very keen on Amalfi coast, tuscany ( since i love tuscan wine ); florence, rome and Venice. Cinque terre is captivating in the pics too. I can skip pisa/ lucca. Would love to hear your comments, thanks

    • Hi Tony!

      Personally, I’d strongly recommend cutting a couple of destinations from your list. While technically you can make it work (especially using day trips), that will be a very exhausting trip and the coastal destinations won’t be at their best in March. At most, I’d pick 3 destinations in addition to Bologna to visit.

      You could potentially do something like this, give or take:

      Florence + Tuscan countryside (as one stop, you can day trip to the countryside from Florence or visa versa)
      Bologna 11-14
      Venice OR Amalfi Coast with your remaining days (Venice would probably be easier).

      That’s my suggestion, but ultimately it’s your call! I’ve certainly squeezed extra destinations I couldn’t bear to leave out before. 🙂

  39. Hi Karen, Thanks for your advice. I will now consider the following, feel free to let me know if this is doable.
    day 1-3 Venice
    day 4-7 Florence ( 2 days in city; 1 day trip siena/ san gimignano/ chianti; 1 day trip hiking in cinque terre )
    day 8-10 roma
    day 11-14 bologna for business
    What do you think?

  40. We are in the planning stages of our 2+ week adventure of Italy. Travel is slated for May of 2021 which will include my wife, 2 daughters and I. We plan to fly into Milan or Venice depending flight tickets. We will rent a car and go for it. We want to drive along the entire coast of Italy with possible multi day stops in some of the bigger cities. Plan to stay in hostels, BnB and occasional hotels. For sure spend a 3 days in Silicy. Thoughts?

    • Hi Daniel! Sounds like quite the odyssey you guys have planned!

      My first thought is that I hope that “+” on the 2+ weeks is pretty flexible if you want to drive the whole coast of Italy! That’s an extremely ambitious plan if you want to stop and see much along the way and also fit in 3 days in Sicily.

      If your time frame is set at around 2 weeks in Italy, I’d consider road-tripping one portion of the country (since you mentioned flying into Venice or Milan, maybe driving from there to a few stops in Tuscany and/or Emilia-Romagna/Veneto/Lombardy along the way depending on what you want to see and then flying to Sicily to close out your trip.

      If you have your heart set on driving the whole thing, I’d either try to extend your time or accept you’ll spend a lot of time in the car, finding and paying for parking, walking from parking lots into the towns and villages you’re visiting, and generally getting from place to place. Driving in Italy isn’t impossible by a long shot and we’ve done it plenty, but by the time you add in all the logistics, Google maps estimates tend to fall a bit short of how long it actually takes to get to each place!

  41. Your blog is so incredibly helpful, thank you! Planning my 1st trip to Italy with my teen girl who’s graduating. Will us two females traveling alone feel safe? I want to not hassle with buses and need some tour guides, private cars. Etc over buses. I can probably do train but needs to be easy cause I get lost easy LOL. I will need everything bought ahead of time and planned out to the T so I won’t be stressed. I want to go about 20 nights but want to see allot then.

  42. Sorry clicked send before I asked my question LOL. Can you please help me itinerary order. I want to spend 20 nights total. 2 in Rome, 2 in Lake Como, 4 in Florence Tuscany area (please list 2 towns for me to stay in there), 2 in Dolomite area, then 1 night in these places venice, Almfia coast, postitano, sorrento, Vernannza, riomaggiore, portofino, bolzano, and Bari. Am I missing any must see places? Is this doable? Also one last place is I want to see at least one place in Croatia. I don’t know which is better dubernick or split and how to fit it in? Maybe fly out of there? Help please thanks so much!

    • Hi Becky! Sounds like some amazing destinations you have on your list!

      In Tuscany, if you want to stay in two places I’d personally probably do Florence + Siena or Lucca if you don’t want to drive, or Florence + a country house/apartment near Montepulciano or Siena if you do plan to drive!

      Your wish list sounds amazing but honestly, with 20 nights that’s probably going to be a bit too much. I’d probably cut Bari altogether, and choose two coastal destinations max (Amalfi Coast area with Positano/Sorrento, or Cinque Terre with Riomaggiore/Vernazza, or Portofino, or Croatia).

      For choosing between Split and Dubrovnik if you do decide to do Croatia, we have a whole post on that–search “Split or Dubrovnik” in the top righthand corner of the site and it’ll come up. 🙂

      I haven’t personally taken a whole trip in Italy alone, but I have many friends who travel solo as women in Italy and love it, and I’ve never had any big problems going out alone, etc. Italy is very used to tourists and generally feels very safe to travel.

      Hope that you guys have a wonderful trip, and happy graduation to your daughter!

    • Hi Haylee,

      It all depends on what you’re looking for!

      You’ll need a coat, and gray/rainy days are worth preparing for, but on the other hand, prices will be lower (in a normal year, who knows what will happen this year), the crowds MUCH lighter, and all the sights still beautiful.

      We sure wouldn’t turn down a January trip to Italy!

  43. Thanks Kate Storm , Your article is so incredibly helpful. Verona, Liguria, Sicily, Abruzzo, Milan the best places you can live in Italy. I like u r article.

  44. Thank you for your very informative article.I am interested in staying in Puglia.Could you recommend a small authentic village on the coast with access to public transport.What would your ideal itinerary for the Puglia region be.Thanks again

    • Hi Frances! Sadly our planned 2020 trip to Puglia got cancelled, so I can’t offer any personal recommendations there yet. Hope that changes soon!

  45. Kate, I can’t get enough of your articles!! We are a family of 4 (2 teen boys), traveling to Italy for the first time! We will be flying into Venice the morning of June 2 2022 and out of Rome June 16. I would love your opinion on our proposed itinerary- trying to keep everyone happy and see a lot without cramming in too much! We will likely be hitting the “high points” when it comes to museums and churches. Right now, we’re looking at…
    2-6 Venice
    6-8 Cinque Terre
    8-11 Tuscany/Florence
    11-15 Rome
    16 fly home
    Would you allocate it any differently traveling with two teen boys (14 and 17)? And/or add in any day trips?
    Thank you so much!

    • Aw, thank you for making my day, Rachel! Truly my favorite part of my job is knowing I help people plan their trips. 🙂

      Your itinerary looks great! I’d consider moving one day from Venice (I adore it, but it’s a small city) to either Cinque Terre or to Florence/Tuscany.

      A second full day in Cinque Terre would allow you to either spend some time at the beach or hike more, while an additional day in Florence/Tuscany would give you a chance to spend 2 full days in Florence (here’s our suggested itinerary for that: as well as take a day trip out to the countryside.

      There are some wonderful day trip options from Rome that you may want to look into since you have 4 full days there (here’s a post: but you can easily keep yourselves busy in the city as well!

      Hope you guys have an amazing time! June is a beautiful month to be in Italy. 🙂

  46. Hello,
    We are planning to travel to a Italy for 3 weeks (the end of March – beginning of April). Do you have any extra insight for traveling with children? Ages: 13 yrs, 8 yrs, 1yr old. I want an easy, mellow trip but still want to hit the major sights. What should we add or take away from your itinerary?


    • Hi! Unfortunately, we don’t have any experience traveling in Italy with children that young, but generally speaking, the itinerary should work as long as you’re willing to cut down the number of activities in each destination (so fewer museums, basically). I’d definitely recommend skip-the-line tickets everywhere you go! I know that Rome has a popular children’s museum, as well, and several of the popular hikes in Cinque Terre are doable with your 8 and 13-year-old.

  47. Your blog is amazing, Kate! I am booking a surprise trip for my partner and we are set to visit Italy for 14 days in April 2022. He is a huge history and art buff, I am definitely planning on including Rome, Florence/Tuscany and Venice from your 2 week itinerary.
    In your opinion would adding in Naples in place of Cinque Terre be stretching it too thin?

    Thanks in Advance!

    • Thanks so much, Dani!

      A surprise trip to Italy–that’s one lucky partner you have! LOL.

      Yes, you can absolutely swap Naples for Cinque Terre, and I’m sure an art/history buff would love it. A fast train (not regional train) from Rome will probably be your most efficient way of getting there.

      Fair warning, since I’m not sure of your travel style, Naples is definitely a bit less manicured than the other cities on your list. I adore it and highly recommend a visit, but just got in expecting a bit more grit (and the best pizza of your life).

      Day trips to Pompeii, Herculaneum, and the Amalfi Coast are very doable from Naples as well.

  48. Amazing post! I have always been fascinated by Italy and its historic colosseum. However, I never got a chance to visit there due to my hectic work schedule and other commitments. But, I will be getting some time off during Christmas. And while I was looking for an interesting travel itinerary, I stumbled upon your blog. It does give me some amazing suggestions that will help me to experience the best that Italy has to offer.

  49. Hello…we are looking to go in 2023 to Italy and were considering this itinerary…We need to make sure we are in Florence/Tuscany on June 18…Is this a bit agressive? Would you consider something different and what is the best way to get around…Car or Train? You also noted day trips from these different places…would Naples be one?

    Travel to Venice 1
    Venice 2
    Venice 3
    Travel to Lake Como to Milan 4
    Milan 5
    Travel to Cinque Terre 6
    Cinque Terre 7
    Cinque Terre 8
    Cinque Terre 9
    Travel to Florence 10
    Florence/Tuscany 11
    Florence/Tuscany 12
    Florence/Tuscany 13
    Travel to Rome 14
    Rome 15
    Rome 16
    Rome 17
    Travel Home 18

    • That looks like a wonderful itinerary, and very reasonable for the most part!

      The only exception is that you have “travel to Lake Como to Milan” in one day… doing a quick stopover at Lake Como would be difficult, I’d choose either Lake Como or Milan to visit.

      You may also want to move one day from Cinque Terre to either Tuscany or Milan/Lake Como, but that’s a personal preference.

      You can easily use the train for all of these places except possibly some of the smaller Tuscan towns, if you plan to visit them. For that, you could either rent a car for a couple of days or book a day tour!

      For Naples, you can take a day trip from Rome, but it’s fairly long. If you plan to visit Pompeii and/or the Amalfi Coast as part of that, plan for a VERY long day and absolutely book a tour! We have a very reputable one listed in our Rome day trips guide:

  50. Hi! Thank you for sharing this wonderful itinerary. We are leaving San Francisco 5/25 and arriving in Rome on May on 5/26 and flying out of Venice on 6/9. I’m hoping we are getting in and out just before the big summer rush and heat! We were considering adding one extra day in Rome and I was wondering what the logic is for going to C/T before Florence? On the map it appears going Rome/Florence/CT/Venice might make the most sense, but I’m sure there is a reason I am not seeing. Would also love to hear your recommendations for the three full days in Florence for a family of 4 including a 15 and 18 year old! Thanks!

    • Hi Abby!

      That’s an excellent time to be in Italy, you guys are going to have an incredible time. 🙂

      The logic for going to Cinque Terre before Florence is two-fold. First, if you travel by train instead of by car (which I highly recommend for this itinerary), you can travel from Rome to Cinque Terre along the coast without switching trains, and you won’t go through Florence or need to double back at all. You’ll also have some beautiful views of the coast along the way!

      The second is simply to break up what you’re seeing on the trip. While Florence and Rome are two very different cities, they’re the most similar of the 4 destinations on this itinerary, and going to Cinque Terre in between them gives you an opportunity to mix things up instead of condensing more art museums/churches/cobblestone streets (all things I adore, just to be clear!) into one portion of the trip and risk getting burned out.

      For the 3 days in Florence, I would recommend more-or-less following our 2 day Florence itinerary (which I’m going to be updating with a bit more detail in the next few weeks, as we just got back from our latest trip!), and then taking a day trip into the Tuscan countryside with the 3rd day, whether that’s by booking a tour or going independently.

      Here’s the itinerary:

      For day trips, many popular tours include Siena, a small town like San Gimignano, and a winery visit. If you’d like something a bit different due to having teens with you, other options include Lucca (you can also add a stop in Pisa if you like), Volterra, Arezzo, Bologna… the sky is the limit! We have a full guide to day trips from Florence here:

  51. Hello! I am so happy I found your blog! Such great hints and tips for each of the areas you are recommending.
    We are heading to Italy for a wedding in Volterra. Flying into Florence and renting a car. After the wedding we are staying and for a week and ultimately ending up in Milan.
    What are your thoughts on breaking up the trip?
    Some of the places of interest from your blogs:
    Livorno, Pisa, Lucca, Cinque Terre (?), Rapallo or a beach, Genoa (?), Milan, Lake Como

    I feel like we definitely have too many places we want to see be for such a short time.
    Would love your input, given we will have a car. 4 adults

    Thank you so much!
    Back to google!

    • What a beautiful place for a wedding! Volterra is incredible (here’s our post on the town if you haven’t seen it:

      As for where to go the week after the wedding, you’re right that your dream list is a bit long, but which areas you pick are totally up to you!

      Personally, I’d recommend doing either Lucca + Pisa + Cinque Terre or Milan + Lake Como + *maybe* one other Tuscan town/city before leaving the area after the wedding.

      Lucca makes a great base in Tuscany (here’s our post: and also has the benefit of being within a quick ride of Pisa for a day trip. You can realisitically day trip to Cinque Terre from Lucca more easily than from Florence, too, or move to the beach and stay a couple of days.

      I love that area, so that’s what I would do if it were my trip. 🙂

      However, Lombardy is also stunning! In addition to Milan and Lake Como, with a full week you could also add a visit to Verona, Bergamo, or even Venice. However, I’d be tempted to split the difference and do about 2 days in Milan, 2-3 days in the Como area, and stay in Tuscany after the wedding to explore a different Tuscan city before heading to Lombardy.

      Hope that helps! You have the benefit of your wish list being pretty well grouped geographically, which gives you more flexibility. 🙂

  52. Hello! Wow your blog is so incredibly helpful. My husband and I are planning a ~2 week trip to Italy at the end of July/early August (I know… it’s soon!), and we’re looking at doing basically this itinerary. I’m curious though – this is a 14 day itinerary but I believe only 9 days are accounted for in your post.
    2 days in Rome, 2 days in Cinque Terre, 3 days in Florence/Tuscany, and lastly 2 days in Venice. Is that right? Am I missing something?
    My husband is really interested in seeing the Dolomites. Is that something you think we could throw in there with that 9 day itinerary?
    Thanks so much! Really appreciated your recommendations.

    • Hi Mari!

      Yes, it’s because the way I laid out this itinerary doesn’t include the days you’re actually traveling between destinations, these are the full days you’re in each area. 🙂 I know it’s a bit confusing, which is why I switched to a day-by-day layout on future itineraries!

      It would be hard to squeeze the Dolomites (or any 5th destination) into a 2-week trip without being extremely rushed, especially because the Dolomites really need more than a day. If he has his heart set on seeing them, I’d consider swapping one of these destinations for the mountains!

  53. Hello,

    Fantastic descovery is your site as Ive just decided last minute to go to Italy.
    Im under a particular schedule going there since Im going for 6 weeks but two of
    those will have to be remote work. So after two weeks of travel one week of remote work.
    Have 100 questions for you but if there would be just one, what would be the places
    you would stop for about a week,considering most my days will be working.

    for sure will have more questions for you as I was thinking of using one of those week
    to go travel in a near by country etc.



    • Ah, that’s a delightful problem to have but a very hard question to answer!

      Really, any city or reasonably-sized town that appeals to you is a great option. If you need to use video or send large files, I’d opt for a city and keep an eye on wifi speeds. If you don’t need particularly fast wifi, just about anywhere (other than perhaps some very rural places) will do.

      We’ve worked for a month at a time from Rome, Florence, and Bologna, and for a week from many, many places including Naples, Palermo, Otranto, Verona, Venice… basically, the sky is the limit!

      Personally, we find quiet neighborhoods in medium-to-large cities generally excellent to work from–plenty of convenience and infrastructure, as well as lots to see on your times off.

  54. Hi Kate!

    I just found your blog today & I’m actually obsessed with all the info you’ve posted! I’m trying to jump start my exploration of the world with my boyfriend so I’m currently trying to plan our Italy trip for 2024! It will be both of our first times & I’ve just been hooked onto reading this 2 week guide… I wanted to ask though as first timers, what would the best itinerary breakdown of each city be for us? As far as how many days in each city & what to do in order to check it off our first timer list? Also if you had to choose between Sept/October to travel to Italy which one would you choose?! I love love love this blog of yours & will continue to reach for it as I plan future trips for my boyfriend & I! (:

    • Thank you so much, Tori!

      The itinerary here, as written, is great for first-timers, but where you start and finish can be swapped depending on whether Rome or Venice is easiest to fly in and out of based on where you’re coming from.

      September and October are two of my absolute favorite months to visit Italy, so it’s hard to choose!

      September will be warmer and a bit more crowded, and depending on the year and which week in September you may even enjoy some late-summer style weather. That’s great for visiting places like Cinque Terre.

      October is cooler, with a higher risk of rain (especially later in the month), but the food is delicious, many of the harvests start, there are fewer crowds, and many perfect weather days. I often say Tuscany is the perfect October destination.

      You really can’t go wrong with either month!

  55. Hi Kate,
    So happy I stumbled upon your blog – most helpful of everything I’ve found online so far! Would love guidance on planning our trip for March 11-25, 2023. This will be the first time in Italy for my husband and near-adult kids – ages 16 and 18. I was in Rome, Florence, Siena and San Gimignano for about ten days, 25yrs ago and have been dreaming of going back ever since!!

    The challenge is that we have to spend about 3 days in Paris as part of this 2-wk trip, and i don’t know how best to organize that. I’d like to go to Rome and Florence for sure; everything else is open. We’ll be flying to/from Florida and don’t know if we should go to Paris first, last… or if it’s just unrealistic to try to do all of it. Maybe we should do 5 days in Paris and the rest in just Rome and Florence?
    Also, ideally, we’d be in Paris for all or part of a weekend, which makes it even more challenging! (Meeting French cousins there and they have to work during the week.)

    Here’s a bit about us: we have lots of energy and are willing to get up early and stay out late and take trains and planes at odd times :). We’re good travelers and are flexible, and yet this shouldn’t be a wild ride – it should have an easy pace but be full of sights, sounds, tastes, and discovery. Cities and small quaint charming towns are superb; we can probably skip coastal towns on this trip since we live near the beach in FL 🙂 If you disagree, do speak up! Happy to take trains and walk a lot, and use the discounted airline you mentioned, as long as it’s safe (!).

    I haven’t looked at the rest of your blogs yet; wondering if you also have recs for olive oil and/or a balsamic tastings/tours and if there’s a guide or an app for being gluten free in Italy!

    Thanks SO much in advance for any advice you can offer! Much appreciated!

    • Hi Laura,

      Happy to help! You guys seem to be the perfect candidates for a busy trip, which is a great thing. 🙂

      If you want to squeeze it all in, I’d recommend either starting in Paris or ending in Rome, or vice versa. If you can find good open-jaw tickets to these cities, your plan is ambitious but doable.

      Assuming you start in Paris, I’d plan about 3-4 days there.

      Your long travel day will be between Paris and Florence–you can either fly, or take a high-speed train to Milan followed by one to Florence (book early to ensure the best prices and direct routes). Both will be a long day, but the train is more fun. 🙂 We use Omio to plan our long train routes.

      In Florence/Tuscany, you can allot 5-6 days. I’d plan to spend at least 2 full days in the city, and then more in smaller towns. You can either take day trips from Florence (by train, car, or tour), or head to southern Tuscany for a few days.

      Southern Tuscany is where you’ll find the Val d’Orcia, as well as gorgeous towns like Montepulciano:

      If you want to take a day trip to Florence but are looking for a different (but still convenient) home base, Siena (as you know) and/or Lucca are amazing cities:

      From there, you can wrap up with a few days in Rome, which will give you time to see the major sites. We have lots of Rome posts, but here’s an example of what you can see with 2 days there:

      Olive oil tours will be at their peak in the late fall (when the harvest is), so it doesn’t overlap with your trip. Traditional balsamic vinegar hails from Modena, which is out of the way for you. However–a good enoteca will be able to offer you delicious tastings of both, and you’ll find those all across Italy (you’ll be spoiled for choice in Tuscany in particular).

      As far as being gluten-free goes, that is not my area of expertise, but I can recommend checking out the guides and translation cards from Jodi at Legal Nomads–she’s a longtime foodie and travel writer who has traveled the world with celiac.

      Have an amazing trip!

  56. Hi Kate,
    I am planning for the first ever european trip for my wife (40) and son (14). I have travelled in other countries of europe for business purpose. I have decided for a two weeks trip to Italy in 2nd half of May 2023. The following is a very very high level itinerary. I am yet to drill down. I have 13 full days.
    Day 1 – Arrival in Rome @ 2 pm. Take a walk in the evening.
    Day 2 – Colosseum, Roman Forum etc.
    Day 3 – Vatican City
    Day 4 – Travel to Florence
    Day 5 – Florence
    Day 6 – Florence
    Day 7 – Florence
    Day 8 – Cinque Terre
    Day 9 – Cinque Terre
    Day 10 – Cinque Terre/Camogli???
    Day 11 – Travel to Venice
    Day 12 – Venice
    Day 13 – Venice
    Day 14 – Venice
    Day 15 – Travel to Rome and take a departure flight @ 4pm

    I am not sure if I should cut down somethings and include any other spots. Can you please review the itinerary and suggest amendments?

    • Hi Nitin,

      Sounds like the workings of a great trip!

      I’d consider moving one of your Florence days to Rome unless you’re planning to use the third day in Florence to take a day trip to the Tuscan countryside/smaller towns. You could also move your third day in Venice to Rome instead. Rome is definitely the biggest city of what’s on your list!

      If you want to see the Riviera beyond Cinque Terre, I’d look into Portovenere–it’s sometimes called the “sixth town” of Cinque Terre, is easily accessible by ferry, and is much less crowded due to being a bit harder to access than the others.

      I’d recommend booking your trains from Cinque Terre to Venice and Venice to Rome well in advance, as you’ll definitely want to take the high-speed trains for those routes.

      Hope you have a fantastic first trip to Italy!

      • Thanks Kate for such a quick response! After doing some more research, I changed the sequence of the travel so that it is easier to fly out of Rome. Some people suggest to remove CT and increase the days for other 3 big cities.
        I am confused. 🙂 What do you suggest?
        Day 1 – Fly in to Rome @ 2pm. Travel to Venice by train.
        Day 2,3 – Venice (Yet to plan detailed itinerary)
        Day 4 – Travel to Florence
        Day 5,6,7 – Florence and nearby areas (Yet to plan detailed itinerary)
        Day 8 – Travel to Cinque Terre
        Day 9,10,11 – Cinque Terre (Yet to plan detailed itinerary)
        Day 12 – Travel to Rome
        Day 13, 14 – Rome ( 1 day colosseum etc. and 1 day vatican city)
        Day 15 – Travel back from Rome to India

        • I definitely agree that it’s a good idea to move some of your Cinque Terre time to Rome!

          While you definitely can enjoy 3 full days in Cinque Terre, with your schedule, 1-2 is plenty. Better to have another day in the Eternal City. 🙂

  57. Hi, Kate: We are traveling to Italy in May and June. Your site has been invaluable in our planning. My first of what I’m sure will be many questions is what train stations in Venice (to travel to Florence) and Florence (to travel to Rome) do we want to use? We are staying as close to the center of those cities as possible.

    • Hi Elizabeth,

      I’m so glad to hear that!

      In Venice, you’ll want to use Venezia Santa Lucia (which is right on the Grand Canal).

      For Florence (both to and from), you’ll want Firenze Santa Maria Novella (which is a 10-minute walk from the Duomo).

      Those are the “main” train stations in each city, so most ticket-booking options should suggest them to you automatically!

  58. I have never been to Italy but am going in July so found your blog really helpful! My daughter will be doing an abroad program in Siena so I will fly over with her 12 days early. Is it a stretch to want to visit Rome, Florence, Cinque Terre, Venice and Lake Como within this time frame when she has to be in Florence on day 12? It would mean flying to Rome and going north from there to hit everything but would have to circle back to Siena. I’d love your two cents on where to fly into- thinking maybe even Switzerland since wanting to see Lake Como. Thank you!

    • Hi Gina,

      Your daughter is going to have such a wonderful time!

      All of the places you mentioned are fantastic, but yes, that’s really too much to fit into 12 days (since you mention your daughter needs to be in Florence on day 12, I’m assuming this is more or less an 11 day trip).

      If it were me, I’d focus on Venice, Rome, and Florence.

      Flying into Venice would probably be most convenient, though Rome would work as well.

      Taking the high-speed train from Venice to Rome (you’ll want to book those tickets in advance) and then traveling from Rome to Florence by train after sightseeing down south will likely make the most sense.

      As far as Cinque Terre goes, a day trip from Florence to Cinque Terre isn’t ideal, but it can be done and in your case may be a way to squeeze in a taste of the coast. We go into more detail on how to do that well here:

      I hope that helps a bit and that you guys have a magnificent time in Italy!

  59. HI Kate! your blog was very helpful. I would love to have your opinion on my upcoming trip. I am taking a transatlantic cruise from NYC to Rome; arriving in Civitavecchia on 10 May 2024. I am lucky and don’t have a time frame. Since Italians take their time… I’m going to embrace that after years of a stressful job, I’m traveling solo as at 37. I want to be loose with my plans, do you think buying tickets for places like the Colosseum just a few days in advance is risky? I was planning on my travel day to purchase tickets for those things. I also have a general route planned and I would love your opinion one this. Since I disembark in Civitavecchia I was going to spend 4 nights in Rome (this is the only things I have booked).
    -4 night in Rome
    -2/3 nights in Naples/ Amalfi Coast (I also would like to go further south but not sure where.)
    -Travel Day to Florence I might stay a night in Assisi or Siena
    -3/4 nights in Florence with a day trip to Pisa and Lucca
    -2 nights in Cinque Terre
    -I think I should go to Genoa or Milan after
    – I also want to spend a night in the Tuscan country side (Under the Tuscan Sun like)
    -1 night in Bologna
    -1 night in Bolozno/ Ortisei for the Seceda
    -2 nights in Venice
    I would really like to experience some real Italian life and this trip is really a scouting trip for a possible move to Italy.

    • Hi Sarah,

      Sounds like a wonderful trip!

      In May, booking a few days in advance for most places (including the Colosseum) should be just fine in mid-May. There are a few attractions in Italy (climbing to the top of the Duomo’s cupola in Florence and visiting The Last Supper in Milan are two of them) that require planning further in advance year-round, but for travelers who are flexible with their plans, most things are doable a few days in advance.

      All of the places you have mentioned are wonderful, but I do think you’ll find there are too many of them! Since you’re going to be booking as you go, I’d just stay open to extending your stays and visiting fewer places.

      I’m not sure if you have a timeline for your trip, but after weeks of traveling it’s safe to say continuing to change hotels every night to every other night will stop being appealing. Plus, traveling more slowly is one of the biggest benefits of traveling for longer–it’s worth slowing down for.

      Good luck!

  60. We are going to Italy in September/October for about 2-3 weeks. Will visit Rome, Florence, Tuscany and Umbria areas. At the end of our trip we would like to visit Assisi, montepulciano , perugia. Our concern is how to get around in those areas. We don’t really want to rent a car but will if that is our only option, what is your suggestion on this?

    • Hi Teresa,

      It’s doable, but takes a bit of finagling!

      The train stations for each of those places are outside the city center (1-3 miles away or so), so you’ll need to take a bus or taxi from the train station to the historic center.

  61. Hi Kate!

    I have been reviewing your site for the last few weeks and my fiancé and I have decided on two weeks in Italy. We’re thinking of flying into Rome and flying home from Venice.

    We have never taken such a huge trip before and I’m curious if it makes sense to book the flights and have the book ends planned and then start doing booking of the meat of travel afterwards? Or should we have everything planned and booked before we even book the flights?

    Thank you!

    • Hi Jessica!

      Personally, we always opt to book the flights first and then fill in the rest of the trip from there. Flight deals and times can impact your starting and ending points, and possibly even shuffle your trip around by a day here or there.

      Everything else–with rare exceptions like festivals, very trendy hotels, etc–is much more flexible compared to flights.

  62. Hi Kate!

    Just going over your blog and absorbing everything! I have a trip planned that has us arriving in Milan on April 29th and leaving out of Rome on May 19th so I’m planning on working our way from top to bottom.

    Rough plan currently is
    Milan -> Venice -> Bologna -> Florence -> Cinque Terre? -> Naples -> Amalfi Coast? -> Rome
    With some day trips mixed in there, most likely to Siena, Pompeii, maybe Lucca/Pisa or somewhere else.

    Would you recommend going to Cinque Terre which we would do closer to the start of May or go to Amalfi Coast which would be closer to mid May? Since you mentioned a day trip from Florence to Cinque Terre is not the easiest, would it make sense to go to the Amalfi Coast instead so I don’t have to backtrack through Florence to get down to Rome or Naples? I’m also concerned about the weather as Cinque Terre is more north and it will be earlier in the month vs Amalfi Coast being more south and more mid month.

    What would your itinerary look like with roughly 3 weeks that works top to bottom?

    • Hi Edmond,

      For both Cinque Terre and the Amalfi Coast in May, you’ll really be gambling with the weather–it might be gorgeous swimming weather, it might be rainy and chilly (happened to us on our May trip that covered both places a few years ago–you’ll notice I’m wearing long sleeves and jeans in some Cinque Terre photos), or anywhere in between.

      Weather aside, since we can’t control that, prices will probably be a bit lower in early May than mid-May, and the Amalfi Coast is the more expensive destination of the two overall–if cost is a factor, that’s something to keep in mind.

      If you’re open to trimming Cinque Terre, it will certainly streamline your itinerary by cutting a transition, so I’d consider it if you’re not married to the idea of visiting two coastal destinations.

      A few other day trip ideas you might consider if you have time: Parma or Ravenna from Bologna, Lake Como from Milan, and Montepulciano and/or some of the other Tuscan hill towns from Florence.

      Your route is very similar to what we’d cover if trying to hit the highlights in 3 weeks, I’d just make sure to cut anywhere that feels like an obligation in order to give more time to the places you’re most excited for (any one of those cities would be an amazing place to spend a week or more).

      Happy planning!

      • Hi Kate!

        Thanks for the info! I’ve done some more research and currently have the following plan

        Day 1 – Milan – Arrive late at night
        Day 2 – Milan – half day and then train to Venice. Half day in Venice
        Day 3 – Venice – Full Day
        Day 4 – Venice – Check out of hotel and explore Venice until ready to leave for Bologna. Night in Bologna
        Day 5 – Day trip to Modena and Parma
        Day 6 – Check out of hotel. Day in Bologna until ready to leave for Florence
        Day 7 – Florence – Full day
        Day 8 – Florence – Full day
        Day 9 – Florence – Sienna or Pisa/Luca day trip or Chianti wine tour.
        Day 10 – Florence – Sienna or Pisa/Luca day trip or Chianti wine tour.
        Day 11 – Train from Florence to Naples or Sorrento and then day trip from Sorrento to Naples.
        Day 12 -Sorrento – Day trip to Pompeii?
        Day 13 – Sorrento – Day trip to Capri?
        Day 14 – Amalfi Coast
        Day 15 – Amalfi Coast
        Day 16 – Amalfi Coast
        Day 17 – Rome half day? Or full day or arrive late night and just have 3 days in rome?
        Day 18 – Rome
        Day 19 – Rome
        Day 20 -Rome
        Day 21 -Half Day in Rome fly home

        I’d like to do a wine tour of the Chianti region but I’m not sure if it’s something I should try to do with a Siena, San gimignano, and Chianti tour or dedicate a full day to it and have Siena/San gimignano as it’s own day. If I dedicate a full day to it I would have to take a day from Bologna, Rome or Amalfi coast. What are your thoughts on this? Do you think we have too much time in the Amalfi coast? I’m thinking of using Sorrento as a base for a few days as I’d like to visit Pompeii, Naples and Capri and then a few days stay possibly in Ravello. Or maybe take Day 17 away from Rome and give it to Florence. That would leave us with 3 and a half days in Rome.

        Love to hear all your thoughts on my above plan and what changes you would make or places that you would switch out.

        These are the places that I’ve wrote down that I don’t think are worth visiting this trip
        Lake Como
        Cinque Terre

        and these are the places that I’m still thinking about

        Do you think Orvieto or Arezzo are worth swapping out for Siena or Lucca/Pisa.

        Thank you!

        • Hi Edmond,

          I’d actually recommend taking any extra time to smooth out the very beginning of the itinerary–day 2 in particular isn’t going to leave a lot of room for sightseeing, in between checking into/out of two hotels, transiting to a new city, etc. Depending on which city interests you more, I’d consider adding a day to either Milan or Venice. As it stands, you probably won’t do more than a few hours of actual sightseeing in Milan–up to you if that’s the pace you’re looking for!

          I do think you can get away with 3 full days in Rome–more is always lovely, but 3 is a solid start.

          Same with the Amalfi Coast–you can certainly have a wonderful time there with the extra day, but I wouldn’t say you need it. Sorrento is an excellent base and you can easily see a lot of the region from there.

          Siena, Orvieto, Arezzo, and Lucca are all wonderful. Pisa is fun, but I wouldn’t call it an absolute must-do unless you’re dying to see the leaning tower–of the five, it’d be the one I’d prioritize least. Other than that, you can’t go wrong with any of them.

          As far as whether to visit the Chianti region as an entirely separate day or combine with Siena/San Gimignano, I’d say that depends on how much of a wine fan you are. Personally, we enjoy wine tastings but one in a day (especially the way they pour in Tuscany!) is plenty for us, and we prefer to mix in sightseeing. If you’re visiting Tuscany for wine in particular and are very interested in learning about the various varietals, etc., though, you might consider separating them out.

          • Thanks so much Kate!

            I was not overly interested in Milan other than the Duomo and Galleria Vittorio which is why I was only planning on spending the afternoon there before heading off to Venice. I didn’t want to skip over Milan entirely but I feel like our time is better spent in other locations.

            Do you think it makes sense to split our time in Naples and Sorrento? Stay in Naples for say 2 days to explore Naples and Pompeii and then move onto Sorrento for 3 or 4 days to explore Capri and the AC? Or would you recommend sticking in one place the whole time? I have heard there is not as much to do in the town of Sorrento and by not having to do day trips to Naples and Pompeii from Sorrento could save some money on transportation?

            Honestly we’re not much wine fans but I thought it was something we should try while we are there. Sounds like mixing all 3 locations into a tour in one day is the way to go!

            If you think the time we have in AC is enough without adding more and 3 days in Rome is enough then it looks like I have an extra day to allocate somewhere. I’ll have to do some more thinking on where to place that extra day. Thanks for all your help so far!

          • Anytime, Edmond!

            Sounds like a solid plan for Milan.

            Personally I love both Naples and Sorrento, though they’re very different–just depends on what you’re looking for. You can day trip to Pompeii pretty easily from either, so I wouldn’t let that sway your decision. But the pizza, views, archaeological museum, underground, etc, in Naples are well worth your time if you can fit it in!

  63. Hi Kate,

    Great work on the site, it’s been super helpful.

    Was wondering if you could gife me your opinion on an issue I am facing. My nieces wedding is in September so we are planning 16 days and wanted your thoughts if this is doable.

    We are arriving before the wedding and have to end in Florence.

    Arrive Rome – 3 nights
    Assisi – 1 night
    Bologna – 2 nights
    Venice – 3 nights
    Modena – 2 nights
    Florence – 5 nights

    Would love your thoughts and thanks in advance!

    • Hi Michael,

      Thank you so much!

      The first thing that jumps out is that you have Bologna and Modena separated–I would definitely combine those! Modena is only a 15-25 minute train ride or so from Bologna, and virtually every train to it is going to require passing back through Bologna regardless.

      Personally, I’d probably base yourself in either Bologna or Modena for one 3 or 4 night period, and take a day trip to the city you’re not staying in. It’ll be much more efficient and if you only stay 3 days, buy you an extra night to add to another city of your choice.

      Bologna is the traditional choice for where to stay between those two: it’s bigger, there’s more to do, and as the capital and transportation hub of the Emilia-Romagna region, it’s easy to navigate to and from. However, Modena is beautiful and offers the benefits of being a more affordable and less crowded place to stay.

      Other than that, your route looks wonderful and is very doable by train, so navigation should be very convenient. 🙂


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