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

Planning the perfect Tuscany road trip itinerary is no easy feat–but it’s well worth getting right.

If you’re dreaming of delicious Italian food, of romantic sunsets and Tuscan wines, of rolling hills peppered with vineyards as far as the eye can see, of hilltop villages and of Renaissance art, this Tuscany itinerary has you covered.

We’ve put this ultimate guide to planning a Tuscany road trip after spending several months traveling in the region over a period of years, often on road trips.

We’ve explored Tuscany by car, train, and tour, in large multigenerational family groups and as a couple, in tiny towns and in the fabulous cities of Florence and Siena.

Honeymoon in Tuscany: rooftops of Siena
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We’ve visited museums, gone horseback riding, zipped along countryside roads on a Vespa, and taken quiet strolls down deserted country lanes. We’ve taken food tours and wine tours, and stopped at more than our fair share of vineyards and restaurants independently, too.

Suffice it to say, we absolutely adore traveling in Tuscany, and this Tuscany itinerary is put together based on our detailed experiences traveling in the region as well as additional research.

We want to help you plan your perfect Tuscany road trip itinerary, especially if it’s your first time in the region.

Here’s what we suggest.

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How We Structured This Tuscany Road Trip Itinerary

We structured this Tuscany road trip itinerary as a loop beginning and ending in Florence.

It’s designed primarily for first-time visitors to the region who want to soak up the classic Tuscany experience: think rolling hills, golden light, scrumptious wine, picturesque hilltop villages, and some of the best food you’ve ever eaten in your life.

… But that being said, even longtime lovers of Tuscany will find something for them here (just ask our extended family).

With this Tuscany itinerary, you’ll visit some of the most iconic places in the region, while also peppering in stops at smaller towns and attractions that would likely go unnoticed if you stuck to exploring via train.

Day Trip to Florence from Rome: View of Arno River

How long will this Tuscany itinerary take?

Is it a cop-out to say that this Tuscany road trip will take as long as you have?

Perhaps, but whether you have 5 days in Tuscany, a week in Tuscany, or a month in Tuscany, this circular route will provide an excellent backbone to your Tuscany road trip.

If your trip is short–say 5 days in Tuscany or less–you’ll be able to shorten your stays in some towns (in a pinch, for example, Pisa and Lucca can be combined into one day), and with a longer trip to Tuscany, you’ll have a chance to adopt a leisurely pace and add in more excursions like wine tasting or days spent at one of Tuscany’s saunas.

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Ideally, I would say that this Tuscany road trip would be spread across roughly 10 days to 2 weeks in Tuscany, but of course, that won’t always be possible–especially if you want to see more regions of Italy during your trip!

If you do have a longer trip to Tuscany planned, we recommend taking a look at some of the additional Tuscany road trip destinations that we’ve outlined below the main itinerary and seeing what other spots catch your eye.

Honeymoon in Tuscany: Views of Tuscan Countryside

Getting Around During Your Tuscany Road Trip

For most people, of course, taking a Tuscany road trip will require renting a car.

We’ll cover some tips and tricks for renting a car here below the Tuscany itinerary (or you can use the table of contents section at the bottom of the introduction to this Tuscany travel blog post to navigate there!), but here’s the short version: we recommend renting a small car in Tuscany through Discover Cars, which will allow you to compare prices and inclusions of multiple companies at the same time and choose the best car for you from there.

We also recommend renting your car only after you leave Florence, which we’ll cover a bit more below, so you likely won’t need one for every day of your trip to Tuscany!

Check rates & book your rental car with Discover Cars today!

Kate Storm on a white Vespa in the Tuscan countryside--riding a Vespa is an incredibly fun experience during a Tuscany itinerary!

Will this Tuscany itinerary work without a car?

Short answer? Yes, it can.

Through a combination of trains, buses, and carefully selected guided tours (we recommend several reputable ones in our Things to Do in Florence post), this Tuscany itinerary can be completed without a car, though the logistics will be challenging in certain places.

That being said, there’s something very special about taking a Tuscany road trip, and by not driving, you will lose out on the charm of seeing some of the smaller towns at night, miss some of the prettiest vistas, and have a little less freedom in planning your trip.

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However, we completely understand that not everyone planning a Tuscany itinerary can or would like to drive, and we fully believe you can have a deeply fulfilling trip to Tuscany without a car–we’ve done it several times ourselves.

And, while you will lose some freedom, you’ll also gain a bit of peace of mind, as driving in Tuscany is certainly not the most carefree driving in the world!

Cone of gelato with a cookie stuck in it held in front of a gelato counter.

The Ultimate Tuscany Road Trip Itinerary

Start your Tuscany itinerary in Florence.

As the capital of Tuscany, Cradle of the Renaissance, and home to the biggest airport (and train station) in the region, there’s no better place to start your Tuscany itinerary than in Florence.

Ideally, we recommend a minimum of two full days here, which will give you enough time to explore all of the major sights.

Marvel at the art in the Uffizi Gallery, soak in the views from Piazzale Michelangelo and more, (window)shop for gold jewelry on the Ponte Vecchio, eat your way through Mercato Centrale, stand in awe of the Duomo, and visit Michelangelo’s masterpiece David in the Galleria dell’Accademia.

2 Days in Florence: The Ultimate Florence Itinerary

We’ve created several guides to Florence based on our six weeks or so spent exploring the city, including a one-day itinerary and a two-day itinerary, so be sure to check those out for more detail.

For this Tuscany road trip itinerary in particular, though, we have a crucial piece of advice regarding driving: don’t pick up your rental car until the morning you leave Florence.

Having a rental car while in the city is not only unnecessary, it’s an absolute burden. Driving in Florence’s historic city center is extremely limited, and you’ll save both money and headaches by ditching the car until you’re ready to hit the countryside.

Day Trip to Florence from Rome: View of Duomo from Piazzale Michelangelo

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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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!

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Start your Tuscany road trip and drive to Lucca.

Laidback and charming, colorful Lucca is the perfect first stop on your Tuscany road trip and an excellent place to grow accustomed to the ins and outs of driving and parking in Tuscan towns.

Lucca is not too big, not too small, and parking is fairly easy to find right outside the city walls.

17 Lovely Things to Do in Lucca, Italy

It also happens to be a gorgeous, relaxing city that is a fantastic place to soak up the ambiance of Tuscany.

While you’re there, be sure to check out the beautiful Piazza dell’Anfiteatro, which, like Siena’s main piazza, is actually an oval rather than a traditional square, and to stroll along the tops of the city’s 16th-century fortifying walls, which are completely accessible to the public.

Don’t miss a climb up Torre Guinigi, either–not only does it boast incredible views of Lucca, but it’s home to several oak trees that are growing in the sky!

Part of the oval square in Lucca Italy, one of the essential stops on your Tuscany road trip itinerary

Stop by Pisa.

I’ll be perfectly honest: of all the places we recommend or mention in this Tuscany itinerary, Pisa is the one I’m least in a hurry to get back to.

It’s generally far more crowded than most of these other destinations–even the very touristy ones–and outside of Pisa’s famous tower and surrounding historic complex, the town is not exactly known as one of the most beautiful or interesting Tuscan villages.

It is, however, incredibly famous, and the Leaning Tower of Pisa itself more than lives up to expectations. The Leaning Tower of Pisa is truly stunning, and far more opulent and beautiful in person than I expected before laying eyes on it for the first time.

If you’d like to see it, we recommend stopping by for half a day on your Tuscan road trip, checking out the tower itself as well as the nearby Duomo and baptistery, and then moving on.

If you’d like to tour the interior of any of the structures, including climbing to the top of the leaning tower, we absolutely recommend booking skip-the-line tickets in advance.

Book your skip-the-line tickets to visit the Leaning Tower of Pisa now!

Kate Storm and Jeremy Storm at the Leaning Tower of Pisa--this bucket list spot is part of just about any Tuscany road trip itinerary!

Make your way to San Gimignano.

Known for its stunning towers (14 of an original 72 remain), long history of wealth due to its prime location along a Roman trading route, gorgeous city center, beautiful views, and convenient location that is roughly equidistant from Siena and Florence, it’s safe to say that San Gimignano is both incredibly popular and well worth visiting.

We adore this beautiful hilltop town, and highly recommend spending at least one night either in town or nearby if you can, in order to enjoy the city without the crowds of day-trippers that tend to take over the streets during the day.

Don’t forget to make time in your schedule for a scoop (or several scoops, let’s be real) of gelato from the world-famous Gelateria Dondoli: as one of the best-known and most acclaimed gelato shops in Italy, it’s a safe bet that whatever you order is bound to impress.

2 Weeks in Italy Itinerary: San Gimignano, Tuscany

Head to Siena.

While today Florence is significantly better-known than Siena, that was not always the case: beautiful Siena was once the military rival of Florence, and the history of the Middle Ages in the region is dotted with stories of their back-and-forth battles.

Today, Siena is known for its Palio di Siena horse race that takes place bi-annually in the oval-shaped Piazza del Campo–when you stand in the middle of the piazza, be sure to picture 20 horses running at full-speed around a packed crowd–it’s truly impressive.

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Siena is packed full of interesting things to do: it’s home to arguably the most beautiful Duomo in Tuscany (don’t forget to check out the Piccolomini Library while you’re in there!), and we absolutely recommend taking the Porta di Cielo, aka Gate to Heaven, tour of the cathedral’s roof if you can–it’s magnificent.

At least once during your trip, climb to the top of one of Siena’s monuments for an epic view–the Torre del Mangia in Piazza del Campo is a popular choice, but personally, we love that the view from the top of the Opera della Metropolitana includes stunning views of the Piazza del Campo from a bit of a distance.

2 Weeks in Italy Itinerary: View of Siena

Spend some time in Val d’Orcia and soak up the Tuscan countryside.

Of all the scenic places in Tuscany, Val d’Orcia might just be the most beautiful of them all.

This UNESCO-recognized valley is home to the Tuscan road trip views of your fantasies, and it truly has to be seen to be believed.

If you have the time in your Tuscany itinerary, we recommend booking at least a couple of nights in a nearby country villa or agriturismo in order to slowly savor the beauty of the region, but if not, even an afternoon drive here is well worth the trip out.

Kate Storm in the Tuscan countryside at sunset with a sun flare on the right side of the photo--Tuscan sunsets are an epic part of any Tuscany road trip itinerary.

Marvel at the beauty of Montepulciano.

Tiny, gorgeous, and home to arguably some of the best countryside views of all the villages in Tuscany, it’s impossible not to be charmed by stunning Montepulciano–and that’s even before you start sipping its world-famous wine.

Marvelous Montepulciano, Italy: Things to Do + Travel Guide

While it doesn’t take terribly long to explore a village this size on your Tuscany road trip, Montepulciano has one of those peaceful atmospheres that you just want to savor.

While you’re there, be sure to stop by the beautiful Piazza Grande, admire views of the nearby Church of San Biagio that is located just outside of town, and to taste the local wine, vino nobile di Montepulciano.

Piazza Grande in Montepulciano right after a rainstorm--this Tuscan town is absolutely worth visiting as part of your Tuscan road trip itinerary.

Pay a visit to Arezzo.

As you turn back north toward Florence to start to wind down your Tuscany road trip, be sure to check out the beautiful city of Arezzo.

Often overlooked on Tuscany road trips, Arezzo is a delightful city that is well worth the time it takes to visit.

7 Amazing Things to Do in Arezzo (+ Where to Stay)

Home to Roman ruins (including the remains of Arezzo’s very own Colosseum), sweeping views of the countryside from the Medici fortress, some impressively well-preserved fifteenth-century frescoes, and a large number of antique shops just waiting to be perused, Arezzo is an excellent addition to any Tuscany itinerary.

Be sure not to miss a chance to climb the clock tower at Palazzo della Fraternita dei Laici right off the main square (Piazza Grande)–the views from the top are absolutely sublime, and it is our personal favorite spot in Arezzo.

Weekend in Arezzo: Things to Do in Arezzo, Piazza Grande

Drive back to Florence & say goodbye to Tuscany.

As your Tuscany road trip winds to a close, head back to Florence to drop off your car, say goodbye, and–depending on time–perhaps visit one or two more sights in the Cradle of the Renaissance as well.

While we’ve set up this Tuscany itinerary to act as a loop, if you’re going to be flying out of Italy (or continuing your Italy travels outside of Tuscany) in a different location, you can also consider dropping off your car in Rome, Milan, Bologna, or even Venice–but keep in mind that you will likely incur a one-way drop-off fee for doing so, so be sure to budget for that if needed!

Fun Things to Do in Florence: Ponte Vecchio

Other Destinations to Add to Your Tuscany Road Trip Itinerary

While this Tuscany road trip itinerary gives a solid outline of the region and is a delightful trip all on its own, for those with a bit of extra time in the area (or those who like to move at a very fast pace), there is an unlimited number of additional destinations you could add to your trip, both in Tuscany and in its surrounding regions of Umbria, Emilia-Romagna, and Liguria.

We’ve outlined a few of each here to give you some ideas as you plan your trip to Tuscany!

Tuscany Honeymoon: Rooftops of Siena

Within Tuscany


The most famous of all of Tuscany’s hot springs has emerged from comparative obscurity into being a full-blown famous photography location in recent years, but there’s no doubt that it’s still a dream to visit–if you have time during your Tuscany road trip to make the trek out there and you’re a fan of hot springs, it’s definitely worth a visit.

21 Romantic Things to Do in Tuscany


Dating back to the Etruscan period and nestled on a hill high above the sweeping Tuscan landscapes it overlooks, the walled city of Volterra is absolutely worth visiting as part of your Tuscan road trip itinerary.

The ease of accessing it paired with its beauty make this one of the first towns we would recommend if you are looking for additional stops along your road trip in Tuscany.

Photo of Volterra as seen from outside the town--Volterra is an excellent addition to any road trip in Tuscany.


Cortona is perhaps best known for the famous book/movie that is based there, but even without the fame brought by Under the Tuscan Sun, this tiny Tuscan town is still a fabulous place to visit!


I’ll be honest: a trip to Elba is a bit of a stretch for all but the longest trips to Tuscany, but it bears mentioning simply for the fact that Elba is Tuscany’s very own island–and “Mediterranean island” is just not what you normally associate with a trip to Tuscany.

Whether you want to scuba dive, enjoy delicious seafood, lounge on the beach, or chase down the island’s interesting history (Elba was the first place Napoleon was exiled to, though he escaped a little under a year later), there’s no doubt that Elba makes a unique addition to any Tuscany itinerary.

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Easier to access than Elba but equally focused on all things coastal, the seaside city of Livorno is the perfect Tuscany road trip destination for anyone looking to enjoy a little sea and sun as part of their trip to Tuscany.


Best known for its delicious Brunello di Montalcino wine, the hilltop town of Montalcino is a delightful slice of Tuscany that is easy to access from Siena and Val d’Orcia.

Cluster of grapes almost ready to be harvested in the Tuscan countryside

Outside of Tuscany

Cinque Terre

Of all destinations outside of Tuscany that people tend to be eager to add onto their Tuscany trip, Cinque Terre almost always falls near the top.

17 Quick Cinque Terre Tips You Need to Hear

We’ve visited this sensational collection of Ligurian fishing villages twice as part of a Tuscany road trip, as well as on a standalone visit, and we can attest that they are well worth the trouble if you have time in your itinerary.

We absolutely do not recommend driving into the villages, however–instead, drive to the train station at La Spezia or Levanto, park your car, and then take the train into the villages from there.

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


Known, above all else, for its food, Bologna is the perfect location for foodies to flock to if they’re looking for some truly epic cuisine during their road trip.

Bologna is the capital of Emilia-Romagna, the region that is home to so many of the things us foreigners tend to associate with Italian food: tagliatelle al ragu (aka spaghetti bolognese), mortadella (aka bologna), parmigiano-reggiano, traditional balsamic vinegar, and more.

21 Best Things to Do in Bologna, Italy's Foodie City

Once you get done eating, Bologna has plenty of other sights to explore, as well–but the food alone is worth visiting for.

The Best Things to Do in Bologna: Climb Asinelli Tower


Set on a hilltop overlooking sweeping views of the Umbrian countryside, Orvieto is as historical as it is picturesque: dating back to the Etruscans and once (briefly) the home of the pope, whether you’re looking to dive deep into the history, enjoy the tasty Orvieto Classico wine, or simply admire the magnificent vistas, Orvieto has something to offer.

We adore this little village–be sure to check out the Duomo, the views from the Torre del Moro, and the underground while you’re there, among plenty of other fun things to do.

16 Cool Things to Do in Orvieto, Italy
View of Orvieto Duomo as seen from Torre del Moro


As the location of the birth, work, and death of St. Francis, Assisi is an enormously popular pilgrim destination among Catholic travelers–but even if you’re not Catholic, this small Umbrian town has plenty of history and beauty to offer.

St. Francis was the founder of the Franciscan Order–a name you’ll see pop up a lot in Italy–and is also one of the patron saints of the country.

In Assisi, you can tour the enormously impressive Basilica of St. Francis while learning about the life and history of the saint.

Tuscany Road Trip 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.

The Best Time to Visit Tuscany

Ultimately, Tuscany is a beautiful destination year-round, and you can never go wrong with a visit.

Spring in Tuscany brings beautiful flowers but plenty of rain, summer brings lots of tourists but also long days and sunshine.

Fall brings the harvest and temperamental weather, and winter brings cold, gray weather but also low prices and a distinct lack of crowds.

If you ask us, though, our favorite time to take a Tuscany road trip will always be in the fall, particularly late September through mid-October.

True, it’s hardly offseason (in other words, there will be plenty of other tourists around), and there’s a good chance of experiencing a cold and/or rainy day or two–but the changing colors across the countryside, the incredible food that is freshly harvested, and the crisp chill that sweeps through the air each evening as the heat dies down for the year give the region a magical quality that we will never tire of experiencing.

We’ve spent at least part of the last few autumns in Tuscany, and we see no reason to stop that tradition anytime soon.

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Useful Travel Tips for Driving in Tuscany

While driving in Tuscany is not the most difficult driving you’ll encounter in Italy (looking at you, Rome and Sicily), it definitely has its quirks!

Here are a few tips we recommend keeping in mind as you plan your Tuscany road trip itinerary.

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Make sure you have access to a GPS for your Tuscany road trip.

This is absolutely imperative, in our opinion, and can make the difference between an insanely stressful Tuscany road trip and a fairly laid-back one: whether you purchase an international cell phone plan through your carrier before leaving for Tuscany or you purchase an Italian SIM card on the ground, you’ll 100% want to make sure you have cell phone data–and therefore GPS–with you as you drive.

Siena Day Trip: Jeremy with Classic Cars

Shop around for your rental car.

I’m almost 100% certain that we’ve used a different rental car company every time we’ve rented a car in Italy–that’s how much the prices can vary depending on your time of travel, pickup and dropoff locations, size of the vehicle, and more.

We recommend searching for your car via Discover Car Hire, which will allow you to check out the rates of several different rental car agencies in Tuscany at once and compare prices and inclusions side-by-side.

Shop for your Tuscnay rental car with Discover Car Hire today!

Cars parked outside of Siena Italy--parking outside of historical city centers is the norm when on a Tuscany road trip!

Buy the insurance–you won’t regret it.

Ultimately, this is up to you–I know some people prefer not to buy additional CDW insurance (aka the insurance that covers damages to the actual car you’re driving, as opposed to your liability to anyone else) on trips–but we buy it every. single. time. in Tuscany and have no regrets.

I don’t want to overstate things, because driving in Tuscany isn’t exactly like driving in the Wild West–but let’s just say that the roads are often tiny, the buildings very close, the parking lots cramped, and the other tourists’ rental cars parked nearby are frequently scratched and dinged in a way that while not horrendously damaging, is definitely something a car rental company would love to charge you for if it happened on your watch.

The peace of mind is absolutely worth it to us–you can price it for yourself when shopping on Discover Car Hire, or purchase a travel insurance policy through that includes car rental insurance (but be sure to double-check the policy, because only some policies cover it).

2 Weeks in Italy Itinerary: Arezzo, Tuscany

You need an international driving permit to rent a car in Tuscany.

Technically, you always need an international driving permit to rent a car in Italy, and that includes in Tuscany.

You can pick this up before you leave home from AAA, and it’s very easy and cheap to do–just a bit annoying, as it’s one more thing to add to your to-do list before leaving for your Tuscany road trip.

Now, that being said–will your rental agency always ask for it? No. Will the police always ask for it? No.

Is it worth the risk of being refused a rental car or getting a ticket over $25 USD and a bit of hassle? Not in my opinion.

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Rent the smallest car possible.

Not only is it cheaper, which is always excellent, but a smaller car in Tuscany is also much easier to drive.

While the highways in Tuscany are pretty standard, this-could-be-anywhere highways, the small country roads, parking lots near villages, and dirt roads leading to vineyards and villas can be incredibly narrow–which, naturally, does not stop them from being used for two-way traffic (you’ll probably end up pulling over to let someone maneuver past you at least a couple of times during your Tuscany road trip).

Be sure to account for how much space you’ll need for luggage, especially if you have three or more people in your group, but other than that–the smaller, the better.

Romantic Things to Do in Tuscany: Sunset over Florence

If you get a ticket, you probably won’t know it right away.

Traffic citations in Tuscany are generally captured via camera, so if you get one, you probably won’t know it right away.

Instead, your license plate will be captured, the ticket will be sent to the owner of the car (ie, your rental company), and then your rental company will forward it onto you.

Unfortunately, that means you won’t be 100% sure you didn’t have any infractions during your Tuscany road trip until several weeks after you get home.

You will encounter toll roads in Tuscany–so carry cash.

Most toll roads in Tuscany will accept credit cards, but it’s always best to have small bills/coins of cash on you–just in case you run into a cash-only booth (or you need a last-minute coffee and/or gelato, which are also very important parts of any Tuscany road trip itinerary).

Best Views of Florence: Girl near Ponte Vecchio

Be prepared to park and then climb up to towns.

Tuscany is known for its delightful hilltop towns, full of winding, narrow streets and plenty of foot traffic.

Combine the above description of Tuscany that we all know and love with the very concept of a Tuscany road trip, and an obvious question emerges: where are the cars?

Usually, they’re in parking garages built literally under the hilltop towns or on the outskirts of historical centers… which means you often have to walk up steep hills in order to reach the center.

Some cities, like Siena, have escalators installed to help alleviate this problem–but in general, be prepared for a little bit of a leg workout when visiting small towns in Tuscany!

View of the countryside from the edge of Montepulciano, an excellent stop on any Tuscany itinerary!

Avoid ZTL zones like the plague.

Essentially, ZTL zones are restricted access zones that dot most of Italy’s historic city centers, including in Tuscany.

If you drive into one, even accidentally, you’re risking a big ticket (and we’ve definitely had to call tiny Tuscan police stations to help some of our family members pay them off months after the fact).

Avoid them by parking on the outskirts of historical centers and by doing your research ahead of time, which leads me to…

Whenever possible, figure out where you’re going to park next before leaving.

This is one of our favorite tricks to keeping stress levels down when driving into a new town in Tuscany: know where the public parking lots are and, when heading out for the day, put your directions on for that particular spot rather than just the town.

This will absolutely cut down on the risk of accidentally driving into a ZTL zone (and therefore getting a ticket), and also make the trip into town much less stressful.

Now, in the interest of full disclosure, this doesn’t always work–occasionally the parking lot you have picked out will be full, or you’ll luck out and find street parking along the way–but in general, it will definitely make your life easier during your Tuscany road trip.

Couple on steps of a villa in Tuscany: Packing list for Europe Summer

What to Pack for Your Tuscany Road Trip

Travel Insurance — We don’t ever suggest traveling without travel insurance–anything can happen, and this is definitely a case of better safe than sorry. We use and recommend Safety Wing for trips to Tuscany.

International Driving Permit — If you’re coming from outside the EU and plan to rent a car in Tuscany, you’ll need to make sure to acquire an International Driving Permit in your home country, before coming to Italy.

It is required for all car rentals in Italy, and while the rental company may not ask, it’s not worth the risk of being refused a car once you arrive or getting a fine if you’re pulled over to be without one. Play it safe and if you plan to drive during your trip, add getting an International Driving Permit to your pre-Tuscany planning!

Small Gravel road in the Tuscan countryside with a vineyard to one side--this Tuscany travel blog post will help you plan the ultimate Tuscany road trip itinerary!

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

Portable USB Charger — Don’t stress about your phone dying while you’re sightseeing: add a portable charger to your Tuscany road trip packing list.

Reusable Water Bottle — You’re definitely going to want to carry water with you as you explore Tuscany (especially during the hot summer). Cut down on plastic waste and bring a reusable water bottle instead!

Honeymoon in Tuscany: Streets of San Gimignano

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 to Italy and avoided rain entirely!).

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 can’t recommend the One Line a Day Journal enough–I’ve been using it for more than a year now and adore it!

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.

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Photo of dark purple grapes hanging on vines in Tuscany. Black and red text on a white background reads "The Ultimate Tuscany Road Trip Itinerary + Travel Guide"

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.

67 thoughts on “The Perfect Tuscany Road Trip Itinerary (+ Driving Tips!)”

  1. I love this website It has convinced my husband and me to go on a driving tour of italy! I actually have a question. How do you know or find out where is the ZTL zones so you can avoid them?

    • So glad to hear that, Ilene! Hope you guys have a great time!

      Your GPS can help you avoid the ZTL zones, but the biggest thing is paying very close attention to the signs, as they’ll be marked there. As a general rule, historic centers of cities are ZTL zones, so it’s safest to avoid those entirely and park outside the center before walking into the town!

      • Hi Kate,
        Do you have any recommendations for accommodations on the Tuscan itinerary? We would be going in Sept 2022.

        • Hi Sabrina!

          Yes, absolutely. We have several properties linked in this post, but if you’re looking for specific towns/cities, we also have recommendations in each of our independent city guides.

  2. Hello,
    You guys look like you have a great life! My husband and I are older than you but have retired a bit early so we can travel while we are still able to move about. We have traveled quite a bit independently throughout the years so we are comfortable going to new places. Your blog is great and has so much useful information. Thank you for putting all of your knowledge out there. I know it’s a lot of work to do so.
    If you don’t mind me asking…we were told you have to have a permanent address at least 6 months out of the year for tax purposes. How do you get around that? Don’t mean to overstep. Thanks!

    • Thank you so much, Joanne! We really appreciate it. 🙂 Residency requirements vary by state, but we maintain a technical permanent address in our home state of Oklahoma where we pay our taxes, maintain our businesses, keep our driver’s licenses up to date, etc. Most nomadic travelers have a similar setup for logistical purposes!

  3. Hello, thanks so much for this post. It’s so helpful! My partner and I are going to copy this for our holiday in June this year. I was just wondering if you could tell me which towns you stayed overnight in? Grazie, Olivia

    • So glad it was helpful, Olivia! Where to spend the night really depends on your specific taste, but from this itinerary, we’ve stayed overnight in Florence, Siena, and Arezzo. We’ve also stayed in countryside villas near the Val d’Orcia and Lucca.

      Since you’ll be driving, we 100% recommend staying in the country at least once–Tuscan villas and agriturismos are absolutely amazing. For staying in the towns themselves, make sure your hotels have parking, but other than that, any and all of them make a great place to spend the night.

  4. My daughter and I just booked a rental car for our trip to Tuscany this summer thanks to your post. I was nervous about driving but you laid it all out perfectly, thank you. We’re going for her graduation present and it’ll be the first time in Italy for us both. Bookmarking your site now for when the trip gets closer. Thanks again!

    • That’s amazing to hear, thank you Susan! Comments like this never fail to make my day, we are ALL about making sure your trip goes perfectly! Hope you guys have a fantastic time, and congratulations to your daughter on her graduation!

  5. Hey, this has been quite useful. Im planning my road trip, but im going clockwise on this route. Since i live in The Netherlands, i will drive in from the north, Florence and start here and after Pisa-Lucca, the last stop instead of heading back to Florence is Cinque Terre, to enjoy a bit of the coast. I will take the advice of leaving the car in La Spezia, but if you had to choose to spend a night in Cinque Terre, which woudl you guys recommend, Vernazza or Manarola?

    • Glad to hear it, thanks Rodolfo!

      Which village is best for spending the night in Cinque Terre is definitely a matter of preference, and Vernazza and Manarola happen to be two of my top 3 favorites (the other is Riomaggiore). You can’t go wrong with either, but I’d recommend Vernazza if you’re looking for something smaller, and Manarola if you want to have access to a wider variety of shops and restaurants. Manarola is a more popular (read: crowded) sunset spot, but both places will quiet down considerably once the day trippers head home.

  6. Wonderful, informative article! I am so glad I found your website. We are hoping to be able to visit Tuscany in summer 2022. Italy is our favourite country, but we haven’t been to Tuscany or Cinque Terre, so I really appreciate the wealth of information on your website!

    • Thank you so much, Cheryl! So glad to hear that. 🙂 Hope you guys have an amazing trip to Tuscany and Cinque Terre!

  7. Hi! I just came upon your site when doing a search for info on an upcoming trip. My husband and I are planning a trip for the end of Oct. We will be renting a car in Florence, spending about two days driving through Tuscany and returning the rental in Rome. I know that’s way too short to do Tuscany justice, but we have a commitment in Venice prior to Florence, and are bookended with a fixed return date from Rome. Where in Florence would be our best choice to rent a car so we can get on the road to Tuscany easily? Same question for returning rental in Rome without having to deal with city driving. Lastly, we are doing some basic research in Tuscany in order to maybe get a place there down the road. Should we consider spending our two nights there in Lucca? Thanks so much and I will definitely be following your adventures!

    • Hi Rohini! There are so many places to rent cars in both cities it’s really impossible to say–I’d keep an eye out for the best deal and then look carefully at the directions. Unfortunately, some city driving is probably unavoidable if you want to make it all the way from Florence to Rome, but you can limit it based on your schedule.

      If you’re just going to relax, Lucca is a great choice! If you want to compare possible areas to own a property in Tuscany though, I’d probably recommend one night there and one night in the Val d’Orcia area. You may also want to consider a look at Siena, depending on whether you want to be close to a city or not.

  8. Hi Kate. Thanks for your quick response! This is very helpful info. I had read somewhere that Tiburtina station in Rome is a good spot for rental return since it would not involve going into the city to return. Would you say that is the case? Once again, thank you for your help!

  9. Hi guys, I imagine you’ve had some ups and downs in your travel in the last 2 years because of Covid. I really hope you’ve been able to stay safe and still continue some of your adventures.
    I found your site and am really keen to follow your path around Tuscany when my husband and I go this year.
    I looked up your destinations and would really encourage you to look into coming to Australia and New Zealand some time if you can. Down Under is a wonderful place and New Zealand has just about everything you could ever want to see in a really small country!
    Thank you for your really helpful and informative site.
    Take care.

    • Hi Sian!

      Yes, there have been many ups and downs over the last couple of years for sure, but luckily things are mostly up right now! We’ve decided to base ourselves in Portugal for the next little bit to enjoy lots of Europe throughout 2022. 🙂 Knock on wood, but hopefully our next Tuscan road trip is just around the corner!

      We’d love to head down to Aus and New Zealand one day! No plans at the moment, but you never know. 🙂

      Hope you guys have a wonderful trip!

  10. Such a great and helpful Itinerary, thank you!

    We’re planning to visit late September and I am nervous about the driving portion – what location would you recommend for pick up, outside of Florence? We’re hoping to get a drive to our first destination (open to anywhere) and then pick up a car – appreciate any extra tips you might have!
    I was surprised to not see any mention of Greve as a stop, have you been? This was what I thought was my main stop in Tuscany but I am now rethinking everything! 😀 We have 5 nights in Tuscany (counted Florence separately as a stop when we head North) and prefer to not spend too much time in the city and want to visit many wineries and enjoy the local food! If you have any very specific favorite wineries to stay at or places to dine, I would love to hear about them!

    Thanks again for such a detailed post! I have a lot to consider 🙂

    • Thanks so much, Cait!

      There’s never enough time for all the towns, lol, but if you want to swap in Greve you absolutely can! We haven’t been ourselves yet but generally speaking there’s no such thing as a “wrong” Tuscan town to visit. 😉

      If you want to pick up a car outside of Florence, I’d recommend taking a look at Siena. By the time you get into the very small hilltop towns like San Gimignano, etc, there may not be car rental agencies available (or if they are, it’ll just be an office and they’ll need to drive the car itself to you from a bigger city–which often comes with a fee).

      Have an amazing trip!

  11. Hi, I am planning a vacation trip to Rome (5 days) and from there a road trip (5 days) to the Tuscan area. I’ve been already to Florence and Pisa. I will like to know cities or towns with good food and scenery off the beaten path. Thanks so much for your time and sharing your knowledge.

    • Hi Loly!

      It depends on how you define off the beaten path, but just about everywhere in Tuscany is further off the path than Florence and Pisa! And virtually everywhere in Tuscany has great food. 🙂

      Arezzo, Volterra, Pienza, Montepulciano are all delightful, some more commonly visited than others. Montalcino is tiny but beautiful.

      We also love Lucca, it’s much quieter in many ways than Florence or Siena.

      A common theme is that if you spend the night in any of these places, they will get much more peaceful and quiet if you spend the night, as the day-trippers will head home.

      Some of the spa towns other than Saturnia can feel off the beaten path, such as Bagno Vignoni. They’re popular, but more catered to tourists from nearby.

  12. Wonderful article – thanks!

    Planning Sept trip – 4 days Rome, 2 days Florence, 3 days Venice (as of now)

    Considering adding a Tuscany component but limited to time. Any suggestions to condensing to 2-3 days as a loop or feasibility of starting in Florence and ending in Venice?

    Any input greatly appreciated.


    • Happy to help, Richard!

      With a 2-3 day driving loop from Florence, I’d recommend driving to either the Val d’Orcia (so towns like Montalcino and Pienza) or a nearby base like Montepulciano, and then basing yourself there for a couple of days. You can drive between a handful of close-together towns, see the landscape, enjoy an agriturismo, do some wine tastings, etc, all within a close distance.

      Driving from Florence to Venice isn’t a go-to suggestion of mine since you don’t need a car in either city, but we’ve actually made the drive ourselves as part of a family trip and it was lovely! Bologna, Ferrara, and/or Padua are easy stops right along the route.

      If you wanted to take a couple of days between the two cities, a loop through Parma, Modena, Reggio-Emilio and Bologna would put you in the heart of Emilia-Romagna, which is the origin of some of the most beloved Italian foods (traditional balsamic, parmigiano-reggiano, etc).

      It’s not the most efficient way to get from Florence to Venice of course (that’d be the high-speed train), but if you want to make a trip of it, you’ll have fun!

      If you do want to consider renting a car in Florence and dropping it off in Venice, though, be sure to ask your rental company if they allow it and what fees they would charge before making any plans.

  13. One of my stops is in Luca and the hotel and parking garage are in the Atlantic. How do I get a permit to drive through it.

    • Hi Stacy!

      I think you may have a typo in there, but I’m assuming you mean you have a hotel booked in the historic center of Lucca? If the hotel offers private parking on-site, you can give them your license plate number and they’ll be able to make arrangements for you.

      If they don’t have parking, you’ll likely need to park outside the walls and walk into the center to reach your hotel.

      Hope that helps!

  14. The parking os not on-site but within the walls.

    So you are saying that all I need to do is call either the garage or hotel with my rental car license number and they would be able to get me a permit to drive inside the walled city to get to the hotel and garage?

    • Hi Stacy!

      In your case, I’d contact the hotel and ask where they recommend you park, and then if you head to the garage inside the walls, look at the map to confirm the directions to access it.

      Essentially, your goal is to avoid the ZTL zones, which trigger an automatic ticket (and technically two–one for entering the zone and one for leaving it). Unfortunately, since all of the traffic controls are done by camera, you’ll have no sure way of knowing at the time you park if you’ve crossed the boundary.

      The public parking within the walls should have a way to access it without passing through a ZTL zone, the concern is taking a wrong turn, etc. If you do need to pass through a ZTL zone (generally speaking in Italy), hotels within the walls can get access for their guests but I’m not sure if yours can since they don’t have on-site parking. These rules also vary from city to city in Italy.

      Generally speaking, in the case that you do get access to a ZTL zone to access hotel parking (I know yours doesn’t have it, but just generally), you won’t get a paper permit or anything like that. It’s all done by license plate and camera.

  15. Hi Kate!
    What an insightful article. I am planning a trip to Itlay in August for 12 days with a girlfriend who has never been to Italy. We are landing in Rome, spending 3 days there, and making our way to Florence by train. We will have 6 days in the Tuscany region and plan to rent a car after reading your article. This is what I am planning for our road trip and what your feedback. Would love to know if you can recommend an amazing winery with meals and wine tasting at one of our stops. I have taken suggestions from your blog on places to see and things to do at each stop:) Am I packing in too much?
    Day 1 – Florence to Lucca to San Gimignano spend the night here
    Day 2 – San Gimignano to Siena to Val D’Orcia spend 1 or 2 nights here
    Day 3 or 4 – Val d’orcia to Montepulciano to Montalcino (not sure about Montalcino)
    Day 4 – Drive to Saturnia from the last destination and head back to Florence

    Thank you!

    • Hi Gira! All of the places you have mentioned are wonderful, but yes, I’d highly recommend cutting a few places from your list in order to savor the others more!

      Driving, parking, walking into historic centers, etc, all eat up quite a bit of time.

      I’m assuming you’re planning a couple of days in Florence on days 5-6. Ideally, I’d recommend only changing your “base” one other time. Montepulciano is a convenient spot as you can reach the Val d’Orcia, Montalcino, etc, from there. Siena is another fantastic option, but it’s definitely a small city, not a tiny town.

      Saturnia is pretty far out of the way from everything else on your list, so unless it’s your dream destination in Florence, I’d consider trimming that. 🙂

  16. Hi,
    Your article is very informative. Thanks.
    One question,
    I understand that leaving anything in the car in Italy is not a good idea as it can be stolen.
    What about these small towns in Tuscany? Is it risky to leave luggage in the trunk when parking there, too?

    • Hi Gil!

      That’s essentially down to your personal risk tolerance. Many people leave luggage in the car when they have no other good option if it is kept out of sight in a locked trunk.

      Obviously, there’s always a small risk with that, but it’s a fairly common practice.

      The most important thing is to make sure nothing visible is left behind.

  17. Hi Kate!

    Thank you for such a insightful article, it has definitely helped to make a road trip through Tuscany feel less daunting!

    Are there are places on your list that are more or less English friendly? We will obviously try to learn what we can in Italian, but it is always helpful to know 🙂

    My husband and I previously visited Florence and did a day trip to Pisa, Siena, and San Gimignano. The scenery was so breathtaking it quickly made a road trip through Tuscany a MUST on our bucket list! Having already visited those places (wouldn’t mind visiting San Gimignano again!), what would be your top picks for 5-6 nights (not including Florence but starting from there)? I would love to make a stop at Saturnia if time allowed. Thank you SO much for your suggestions!

    • Hi Samantha,

      Thank you so much! Glad we can help. 🙂

      Unless you go exceptionally off the beaten path, you won’t have any problem using English (plus body language/hand signs/etc) in Tuscany, so don’t worry! Definitely learn what Italian you can, but Tuscans are very friendly and exceptionally used to foreigners.

      Since you guys have already done quite a bit in the northern part of Tuscany, I recommend heading to the southern part! Montepulciano, the Val d’Orcia (including towns like Pienza and Montalcino), Cortona, and Saturnia, make a great loop.

      You might also look at taking a day trip to Civita di Bagnoregio, Orvieto, Perugia, or Assisi. Those places aren’t in Tuscany but are wonderful, and depending on your itinerary might make fun additions.

  18. This is so helpful Kate, THANK YOU!!!! This will be my first time in Italy, I’m traveling solo, and I’ve never driven outside of the U.S. before, so I’m thinking I’ll stick to trains to get around this time (which I know will limit how much flexibility I have). Are any of these towns easily accessible by train from Florence (and/or each other)?

    • Happy to help, Tara!

      Yes, Lucca, Pisa, Arezzo, and Siena are all easy to get to by train.

      The smaller hilltop towns are generally harder to access without a car, and many don’t have train stations. You can technically get to Montepulciano by train, but the station is outside of town and you’ll need to catch a bus or taxi to get all the way there.

      If you want to visit a few of the tiny hilltop towns, I’d recommend signing up for a day trip one day–we link a some popular ones in this post:

      Generally from Florence, you can find either day trips that focus on the north (San Gimignano is a common stop) or the southern Val d’Orcia towns. They’re a great way to see harder-to-access spots while letting someone else deal with the driving and parking!

  19. Hi Kate!
    Thank you, thank you, thank you for the wealth of information. Very helpful for our upcoming visit!

    Any possibility of emailing you directly with a few more questions?

    Lori and Steve, USA, coming in October for our 60th birthday’s!!!!

    • Hi Lori,

      Yes, of course!

      We’re not travel agents and don’t plan/book trips for people, but we’re always happy to answer a few questions and point travelers in the right direction. 🙂

      Happy early birthdays!

  20. Hello again,
    We will only have about 4 (3 full) days and nights to explore Florence and Tuscany. We hear that Florence is not terribly large and is very walkable? Would it be practical and safe to utilize motor scooters to do so? The countryside is a PRIORITY, but we are considering not venturing too far from the city to limit travel time. We’d like to spend at least one night in the city, and at least one in the country. And we very much want to explore a couple of very small villages.

  21. Would you recommend purchasing train tickets in advance, or is it really not necessary? Likewise for renting a car, and making hotel reservations (First week of October).

    • Hi Lori!

      For the train tickets–it depends. For high-speed trains across long distances, like from Florence to Venice, yes, absolutely book in advance. The prices increase dramatically as you get closer to your dates.

      For regional/slow trains, like taking a day trip from Florence to Lucca, there’s no need to book in advance.

      What gets a bit confusing is that some lines, like between Rome and Florence, have both high-speed trains (essential if you’re making a day trip, as it takes under 2 hours), and regional/slow trains, which depending on the exact timetable can take anywhere from 3-5 hours or so.

      If you want an overview of what’s available, we recommend using Omio to search for tickets and compare prices/timetables.

      For hotels and a rental car, yes, you’ll want to book in advance. It’s not as urgent as in, say, July, but to get maximum availability it’s best to be prepared, especially if you have special requirements for your rental car such as wanting to rent an automatic.

      I hope that helps and that you guys have a great time! October is our favorite month to be in Tuscany. 🙂

  22. My daughter & I will have 5 days in Tuscany, have a rental car & want to visit mostly hill towns. Our hotel is outside Florence. We’d like to drive to Cortona then to for wine tasting, then to Monticchiello for a 7:30 dinner at Daria & spend night. Is this possible? Where do I find city maps?

    • I think you mean you plan to spend the night in Monticchiello? If so, yes, that will probably work well. Cortona is a bit out of the way as far as Tuscan hill towns go, but it’s very popular!

      For city maps, your hotel will usually offer one, especially if you ask. For towns that you just take a day trip to, the easiest way to find them is to head to the tourism office (there’s virtually always a well-marked office in the town center).

      Some tourism offices do charge a nominal fee for maps, so it’s a good idea to have a few Euros in small coins/bills on you when you go.

  23. Totally loved it!!! Would you recommend doing this roadtrip with a child? I really want my 5year old daughter to witness new cultures and enjoy some holidays with mum and dad!

    • Of course it depends on the child, etc, but it’s definitely possible! Italy is considered to be very kid-friendly, and kids are adored and welcome just about everywhere.

      The distances in this road trip are also fairly short, so no extremely long car days to contend with.

  24. Hi Kate,

    Thank you very much for your article, it was very helpful to consider the cities/town to visit in La Toscana. What would you recommend me for a 10-day trip (honeymoon 🙂 ) by arriving to Rome? For sure, I want to rent a car and do all by car.
    Would it be better to take a train all over to Florence and from there do the trip all over to Rome?
    Is it a big deal if I do not have an international license?
    Thank you for your help.

    • Hi Andres,

      You can definitely structure this trip as a road trip from Rome to Florence, touring Tuscany by road trip along the way instead if you prefer. For that version, you’ll likely want to start at Montepulciano and then make sort of a “V” shape ending in Florence. Keep in mind that you’ll probably have a one-way car rental fee if you do it this way.

      In that case, you may want to add on a stop in Orvieto along the way as well–it’s in Umbria, and a beautiful place:

      Having an international driving permit is required for non-EU drivers in Italy. It’s not often asked for, so you can choose to take the risk, but your rental company can refuse to rent to you and of course, you can have issues if you get into an accident, etc, if you don’t have one as well. They’re not complicated to get, so it’s much better to acquire one before going to Italy!

  25. Hi!
    Thank you so much for this wonderful site – it is so informative!! We are planning 2-3 days traveling from Florence to Rome and wonder if there are private drivers for hire in Tuscany. Is that an option? And, if so, do you have a sense of how we would locate good drivers? Our concept is that it may be easier on us if we just left the driving to a trained professional local… your thoughts?
    Thanks again!

    • Hi Paul,

      We’ve never hired a private driver in Tuscany, so I can’t speak to that personally! I know that some private drivers and tours advertise through Get Your Guide. Other than that, I’d recommend asking your hotel concierge, they’ll no doubt know of someone.

      However, if your goal is to travel between Rome and Florence, you could also easily take the train. If you’d rather take 2-3 days to do the journey and sightsee along the way, Orvieto and Siena are both stops to consider on the way.

      If you’re confident drivers, though, that route is fairly simple–lots of highway driving, etc. If you’re considering the option of driving yourselves, I’d say there’s no real reason not to.

  26. Hi Thank you for putting together all this info, it has filled me with excitement thinking about our trip this year. My husband and I are hoping to fulfil my dream of travelling to Tuscany this year at the start of April. We will be driving from the UK and stopping off in Normandy then driving across to Italy and Tuscany. The first large city we will enter is Turin before moving towards Tuscany. We have 7 days in Italy but we thought a circular road trip would be great made up of countryside, wine, food and wandering around towns and markets. I love the road trip based around Florence but given our route and our starting point, would you be able to recommend anywhere we should visit/stay/avoid that starts further north and drops into Tuscany. I don’t want to disappoint myself by making poor choices in destinations so any help would be much appreciated. Thank you

    • Hi Kerrie,

      Sounds like a wonderful trip! We’ve driven from Portugal to Italy and/or France (and back) several times ourselves, so we’re very familiar with the breadth of the drive you’re taking on.

      The Langhe region of Piedmont, located close-ish to Turin, is fantastic: think small towns, gorgeous views, delicious wine, and fewer crowds than Tuscany. You may want to consider a stop there before heading further south! We loved La Morra in particular, but there is lots to see around there, including Alba, Barolo, etc.

      Depending on what route you take in, you may pass through Emilia-Romagna as well, one of our favorite foodie regions in Italy. There are a million places to fall in love with there, but Parma might be right along your drive:

      Hope you guys have a fantastic trip!

  27. Hi, I loved your article. My husband and I are planning to head to Tuscany in September. My thought is to arrive in Florence from the states and stay for 3 nights. Originally I was planning to head to Greve and stay at Borgo de Cabrea. for 5 nights and just do day trips from there. (The pictures of the hotel views blew me away). However after doing some more research, I’m thinking that I would leave Florence and head down to the Val d’ Orcia region for two nights, do some day trips from there, then head back up to the hotel in Greve for my remaining 3 nights. I don’t want to short change my experience in southern Tuscany. Looking for advice on where to stop on the way down, and the way up versus day trips from where we are staying. I’m thinking of stopping in Sienna on our way back up since it’s closer to Greve then we can avoid a day trip back down. Where do you think is good place to stop on the way down vs. places that would be better as day trips? Also any advise on where to stay in Val d’ Orcia region? Thanks for the advise on the cars. The site you suggested is much cheaper than the one I was originally looking at.

    • Hi Carol,

      Those hotel views do look incredible!

      With the caveat that you can’t make a very wrong decision in Tuscany, I’d recommend spending 3 nights in the Val d’Orcia area and 2 around Greve. Definitely check out the tiny town of Montefioralle when you’re in the Greve area, too:

      Siena is a decent-sized city rather than a hilltop town, so I’d spend more time there than you can–but if a couple of hours is all you can spare, visiting the Piazza del Campo + the Duomo + visiting one of the viewpoints to see the city from above will make for a memorable stop.

      As for where to stay in the Val d’Orcia, we’re partial to Montepulciano as a base. It’s not in the Val d’Orcia, but nearby, well-connected, and beautiful. Pienza also makes an excellent base and has some hotels whose views I think you’ll also love:

      Depending on which route you take down from Florence, you may pass Monteriggioni, if so, that’d be a lovely stop during your drive.

  28. Thank You so much for your response. After doing some of my own research and keeping your advise in mind, we booked a hotel in Montepulciano. I have another question for you. We are renting a car and tried discover cars. The prices for renting a compact car through Noleggiare are significantly cheaper than any other company. We need an automatic so it can get pricey. The reviews are mediocre and I was wondering if you had any experience with them. Thanks!

    • Hi Carol,

      I don’t think we’ve ever used them in particular, but in general, we’ve never had any issues with a car rental in Italy and have zero brand loyalty with rental cars there. We tend to go with whoever is most affordable, as the prices can vary so much. We do buy rental insurance, though–for us, it’s worth the peace of mind.

  29. Hi
    Planning on driving from Rome to Florence, taking our time. Where would you rent the car? And can you drop off a car in Florence if you rent in Rome.

    • Hi Sebastiano,

      Personally, we’d rent the car in Rome wherever we could find the best deal–we’re not particularly loyal to any one car rental company.

      You can definitely rent a car in Rome and drop it off in Florence, however, you’ll likely incur a one-way rental fee. These can vary dramatically, but are usually pretty reasonable if you’re picking up and dropping off the car in the same country (driving from Italy to Switzerland, for example, would be a different story).

  30. Hi! I liked your insights very much, I hope to go visit Tuscany soon with my family. Though you didn’t really mention seaside areas – I guess it’s because people don’t tend to visit Tuscany region because of beaches, but still, there IS some seaside (judging from map sorry), and I would like to know more, either if you had any experience, or from locals or friends. I clinged to the one photo of a beach at Livorno. I was wondering, if it is worth seeing the seaside as well, if there are any beaches, maybe areas where swimming is not recommended, dangerous tides, sharks… or are there nice places as well, worth visiting. Is the shore easily accessible? The shoreline area is more flat I guess, less hills there as I assume again, from maps…

    • Hi Kate,

      You’re right, I didn’t include seaside areas because typically, that’s not what non-Italian travelers are looking for from the Tuscany region. You’re right that it has a lovely coastline, though!

      A few popular beach towns in Tuscany include Viareggio and Forte dei Marmi. Livorno is a popular cruise ship stop, and has a historic fort right on the water. Don’t miss the view from Terrazza Mascagni if you go!

      If you want to go further off the beaten path, the Tuscan island of Elba (where Napoleon was once banished to) is beautiful.

      If you’re in a beach town, you’ll definitely have access to the sea!

  31. Will be in Tuscany for four days and thinking one day each in Pisa, Florence and Montepulciano (or combine a couple (like Pisa/Florence). Can you suggest a good home base area? We will have a car – any suggestions for a couple of one day road trips (if we can combine P, F or M) to visit wineries, different towns, etc? So many things to see it’s hard to decide and are hoping you can help us out. Thank you so much!!!

    • Hi Collette,

      If you plan to have a car, I’d recommend staying outside a city center and enjoying the countryside a bit. That’s the advantage of having a car in Tuscany!

      I’d also recommend combining Lucca with Pisa–Pisa doesn’t take long to see, but Florence definitely takes a full day at a minimum assuming you want to go inside a museum, up a viewpoint, etc.

      On the route from Florence to Montepulciano, Monteriggioni and Siena are great options (depending on which route you take). The Chianti area is also between the two, though it’s a bit more out of the way to access!

      San Gimignano and/or Volterra would also make a great day, and would be enhanced by having a car.

      Deciding where to stay can be fairly flexible, as all of those places can be visited as a day-trip from the others, but I’d choose based on your priorities, as you’ll have some long drives round-trip. The Siena area makes a great base if your priority is Montepulciano and towns like the Val d’Orcia. The Lucca area or Chianti area is lovely for accessing northern Tuscany (Florence, Pisa, San Gimignano, etc).

  32. Ciao! Thank you so much for writing so much about Italy! It’s been very helpful while planning our upcoming Tuscany road trip. We’re planning to rent a car from Florence and are seeing a lot of negative reviews on all the cheaper Discover Cars rental companies. What rental companies have you used in the past and would you recommend them? Also, are there any we should stay away from? Trying to be budget friendly but also do not want hit with a bunch of fees after the fact. Thank you so much for your help!

    • Hi Natalie,

      Happy to help!

      Honestly, I could not even remember all the rental companies we’ve used in Italy, let alone in Europe. We’re not picky–we’ve used everything from big brands like Hertz and Sixt all the way to tiny local outfits that we spot on the ground. We’ve never been charged for damage, but we do take precautions.

      Specifically, we ALWAYS thoroughly photograph and video (a full 360 video) the vehicle when picking it up, and we tend to buy the additional insurance as well. If you want to ensure there’s a 0% chance of being charged for anything, most companies offer a $0 deductible (in Europe, a deductible is called excess) policy. It’s an increase in the upfront budget, but offers a lot of peace of mind if it’s something you’re worried about!


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