2 Weeks in Italy: The Perfect 14 Day Italy Itinerary

Italy is one of those countries that we just can’t quit–and we think that after following this 2 weeks in Italy itinerary, you’ll agree!

After spending more than a combined 6 months exploring the country in-depth over the last few years, 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.

We’ve made our way to 11 of Italy’s 20 regions, from the imposing Dolomites of South Tyrol to the beaches of Sicily. We’ve “lived” for a month each in 3 different Italian cities (Florence, Bologna, and Rome), taken food tours and cooking classes, explored on foot, marveled at architecture, art, and ruins alike, discovered offbeat neighborhoods, and hit up all the most famous sights (sometimes more than once). We’ve traveled as a couple, with extended family, and with friends.

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.

4 Days in Rome Itinerary: Streets of Centro Storico

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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!

3 Days in Venice in November: Small Canal

Rome: 2 Days

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?

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

Two days in Rome 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.

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!

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.

2 Days in Rome: An Epic & Easy Rome Itinerary

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.

Stroll through Centro Storico.

The Trevi Fountain, the Pantheon, the Spanish Steps: what do all of these famous things to do in Italy have in common with each other? They’re all within walking distance of each other, and all free to visit.

2 Day Rome Itinerary: Street Corner in Centro Storico

Things to Consider in Rome

Rome has two major downsides as 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 we found Rome to be remarkably uncrowded in December), and/or waking up extra early to enjoy the city before everyone else gets out of bed. For example, some of the best photos of the Trevi Fountain, Colosseum, and Spanish Steps that we’ve taken were snapped around dawn!

Rome Off the Beaten Path: 30 Epic Hidden Gems in Rome

That being said–there are a million ways to get off the beaten path in Rome no matter when you visit, and 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 ate at several times on recommendation from the clerk at La Cornice. Just a 5 minute walk away, their lunch special offered a choice of about 10 main courses plus bread, wine, and one of several desserts for 8 Euros/person–it’s hard to beat that!

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 to 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

Cinque Terre: 2 Days

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.

Since five 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 to save a tiny bit of cash.

View of Vernazza Harbor from Above: One Day in Cinque Terre Itinerary

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!

The Perfect One Day in Cinque Terre Itinerary

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).

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 in 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 or the’s famous trail to get around in Cinque Terre.

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 (happened to us 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?

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.

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 likely only give you one day to explore the coast 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.

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

View of Riomaggiore at Sunset, Cinque Terre in One Day

Where to Stay in Cinque Terre

Of the five villages, 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.

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!

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

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!

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

Scorci di Mare (Riomaggiore) — Want to stay a 3-minute walk from the beach and see the sea from your window? Scorci di Mare is the perfect spot for you. Riomaggiore is the smallest village in Cinque Terre, making it the perfect reprieve from busy days (and all the other villages are a short train ride away).

Check rates and 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 and book your stay at Da Baranin!

Ca de Lelio (Manarola) — With cozy, modern rooms and a great location in Manarola, Ca de Lelio will have you perfectly situated to explore the villages.

Check rates and book your stay at Ca de Lelio!

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

Florence/Tuscany: 3 Days

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 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.

Pisa is a popular choice that is close to Florence, but unless you’re truly dying to see the leaning tower, we’d recommend using Siena, Lucca, or Montepulciano as a base instead. If you’re looking for day trips, San Gimignano, Volterra, Arezzo, and Cortona are all stunning, and though it is in Umbria rather than Tuscany, we adored our visit to the village of Orvieto as well.

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.

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.

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

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 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.

Take a day trip to the Tuscan countryside.

Wine + incredible Tuscan food + rolling countryside + 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 in Tuscany

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 itinerary is already fast-paced, there’s no reason to take up extra time moving hotels.

2 Days in Florence: The Ultimate Itinerary

We’ve visited Tuscany both ways: by staying in Florence and commuting out, and by staying near Lucca and commuting into Florence for a day trip. 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!

75 Fantastic & Fun Things to Do in Florence


Bargello Guest House — Located in the heart of Florence, this property is only a short (read: less than 5-minute) walk away from some of Florence’s highlights like the Palazzo Vecchio. Staying here, you’ll be within easy walking distance of the best of what Florence has to offer.

Check rates & book your stay at Bargello Guest House!


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 for one day in Florence!

Check rates & book your stay at Hotel Lungarno!

Romantic Things to Do in Tuscany: Tuscan streets in rain

Venice: 2 Days

Canals, canals, and more canals: Venice is simply a ridiculously beautiful place, and despite its somewhat controversial reputation, we absolutely adore it.

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.

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

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.

The Ultimate 2 Days in Venice Itinerary

Hit the water and enjoy Venice’s canals.

We go into more detail about this in our 2 day Venice itinerary, but 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.

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

Things to Consider in 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. 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–about $100 USD/gondola worth. We opted to skip the gondola ride and simply ride a waterbus through the Grand Canal for about $8 USD/person, which was more than enough time on the water for us.

If you have your heart set on a gondola ride, though, be sure to budget for it!

Couple in front of Bridge of Sighs in Venice

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 a fair trade in exchange for their competitive prices in a great location in Cannaregio. 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 to the vaporetto to the airport. 

Check rates & book your stay at Hotel Casa Boccassini!

3 Days in Venice in November: Was It Worth It?


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: 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 great, and the included breakfast 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!

Photo of Venetian Lagoon as seen from the Doge's Palace in Venice


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.

Check rates & book your stay at Hotel Danieli!

3 Days in Venice in November: Venice from San Marco Bell Tower

2 Week Italy Itinerary Map


More (Or Less) Time 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 find yourself with more time in Italy, consider heading to the South Tyrol region to experience the Dolomites (also known as the Italian Alps). 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.

101 Important Travel Tips for Italy

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.

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.

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. There is always a reason to come back.

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.

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

Visiting Pompeii & Mount Vesuvius: The Complete Guide

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 within 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 sometimes 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. 

How to Travel from Florence to Bologna (By Train!)

We typically book our train tickets through Trenitalia, Italy’s national company, but other companies like Italo are also excellent options on some routes (we recently took an Italo train from Turin to Venice and it was incredibly comfortable).

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.

Keep in mind that most 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. When in doubt, ask before boarding!

Shop train tickets in Italy now!

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). 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.

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An international driver’s permit is required for renting a car in Italy and must be obtained in your home country before arriving. 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.

If renting a car is the right choice for you, we recommend checking out Discover Car Hire. They’ll 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.

Price out rental cars with Discover Car Hire 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.

You can find some buses available, however, especially among smaller cities and villages (we’ve used local buses in South Tyrol several times), so be sure to check for these services as well if you’re having trouble deciding how to get around a certain destination.


When traveling long distances in Italy–say, from Rome to Venice–we strongly recommend looking into flights. Trains are a lovely and romantic way to travel, but they can also take a long time!

Budget flights within Italy can help keep costs down–for inexpensive tickets and airlines, look for flights to and from Rome, Pisa, Bologna, Milan, and Venice.

2 Weeks in Italy Itinerary

When to Visit Italy

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.

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 some 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.).

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

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.

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–here are a few things to be sure to bring!

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

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.

Best Quotes about Italy: square in Lucca

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.

The Ultimate Packing List for 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 a year now and adore it!

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!

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

106 thoughts on “2 Weeks in Italy: The Perfect 14 Day Italy Itinerary”

  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!

  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: https://www.ourescapeclause.com/trip-to-italy-cost/

      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): https://www.ourescapeclause.com/one-day-in-naples-itinerary/

      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 Booking.com 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: https://www.ourescapeclause.com/2-days-in-florence-itinerary/) 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: https://www.ourescapeclause.com/best-day-trips-from-rome-italy/) 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.


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