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.
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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.
Table of Contents
- How We Structured This Tuscany Road Trip Itinerary
- How long will this Tuscany itinerary take?
- Getting Around During Your Tuscany Road Trip
- Will this Tuscany itinerary work without a car?
- The Ultimate Tuscany Road Trip Itinerary
- Other Destinations to Add to Your Tuscany Road Trip Itinerary
- Tuscany Road Trip Itinerary Map
- The Best Time to Visit Tuscany
- Useful Travel Tips for Driving in Tuscany
- What to Pack for Your Tuscany Road Trip
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.
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.
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.
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!
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.
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!
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.
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.
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!
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.
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!
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.
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!
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!
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.
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.
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.
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.
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.
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.
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.
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.
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!
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!
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.
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.
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.
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.
Outside of Tuscany
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.
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.
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.
Once you get done eating, Bologna has plenty of other sights to explore, as well–but the food alone is worth visiting for.
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.
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
The Best Time to Visit Tuscany
Ultimately, Tuscany is a beautiful destination year-round, and you can never go wrong with a visit: spring 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.
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.
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.
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!
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 World Nomads that includes car rental insurance (but be sure to double-check the policy, because only some of their policies cover it).
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.
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.
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).
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!
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.
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 World Nomads 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!
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.
Nalgene — 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!
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!).
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.