Which places to visit on your Tuscany road trip?
As the capital of the region, the beautiful city of Florence is the perfect place to start your Tuscany road trip. Especially if you fly to Italy and grab your rental car here. For me, Firenze is one of the most gorgeous cities all over Italy.
So spend a few days here to soak up the first Italian flair, stroll through the old alleys, gaze at its historic monuments, have amazing pasta, and of course, your first scoop of gelato! Here you can also find one of the nicest places to enjoy the Tuscan sunset with an incredible view across the city.
To do in Florence:
Walk across Ponte Vecchio – the iconic bridge with houses on it
Walk up to or take an e-bike tour to Piazzale di Michelangelo for the best view across the city, especially for sunset when it’s tinted in orange light
Visit the cathedral Santa Maria del Fiore – one of the most beautiful cathedrals in Italy
Visit the Uffizi
– the famous gallery showing many of Da Vinci’s stunning pieces of art
In Lucca, you can take a step back in time. Let the high medieval alleys carry you back a few centuries, as you linger past huge shop windows that let you imagine the old, wooden gates of stables. Right in the heart of the center, you reach a very special Piazza which is not a square, but an oval. Can you guess why? It was built right on top of the ruins of an old theater, that’s why it’s called Piazza dell’Anfiteatro.
But the real highlight encircles the city: Its medieval, well-preserved city wall, designed by none other than the famous Leonardo da Vinci who was born nearby (but we’ll get to that in a bit). You can actually walk (or even bike) the whole historic 4 km all around Lucca.
To do in Lucca:
Visit Torre Guinigi – this tower gives you the perfect panoramic view across Lucca with several old oak trees on top
Walk across the ancient city walls “Mura di Lucca” – You don’t have to do the entire 4 km. And you don’t even have to walk. You can rent bikes or just take a seat close to one of the gates.
Stroll through the old, cobblestoned alleys to Piazza dell’Anfiteatro – as you enter the oval-shaped piazza you get a hint of the feeling it must have been entering the Roman theater
Acquedotto del Nottolini – Take a short walk outside of town and admire this old aqueduct that used to carry water to the town. The perfect photo spot!
Does the name ring a bell? As we’ve talked about the ancient walls of Lucca designed by the famous Leonardo da Vinci, you may have guessed it. Vinci is the birthplace of Leonardo da Vinci and therefore definitely worth a day trip.
A gorgeous old town with steep alleys and a nice castle from where you can enjoy the views across the beautiful Tuscan countryside. And of course, there’s a great museum packed with da Vinci’s sketches and models of his inventions and lots of info about the life of this impressive man.
To do in Vinci:
Well-known for its failed landmark that then turned out incredibly famous, Pisa has become a tourist magnet. The Leaning Tower of Pisa is one of Italy’s best-known and also most visited sights.
Did you know that the tower is actually the bell tower of the dome next to it? So when you look at the tower, don’t miss to turn around and gaze at the beautiful Dome Santa Maria Assunta.
And here are some more fun facts: Only a few years after the start of the construction the tower started to sink due to the unstable soil. In an attempt to compensate for the tilt, the upper stories have a less leaning angle than the lower ones. So the tower is actually slightly curved.
It hasn’t been allowed to climb the tower for many years due to consolidation work.
While the history and construction of the famous tower are interesting, there are honestly much nicer and more authentic towns on your Tuscany road trip.
If you decide to visit Pisa, do it in the early morning hours (before 9 a.m.) or late afternoon hours (after 6 p.m.) to enjoy the place without the day tourist crowds. And don’t forget to take a stroll through town and not just stop for the tower.
To do in Pisa:
The historic center – Don’t miss lingering through the winding alleys of the historic center
The river – Take a walk along the river Arno
Outside of Pisa – Stop by the Via del Gombo in Parco San Rossore, a beautiful cypress avenue
Central & southern Tuscany
What do you think of when you hear “the medieval Manhattan”? Yep, it’s an old town full of towers. What used to be over 70 towers, only 14 remain today. But they still dominate the appearance of the town. While all Tuscan towns are well-known for one or a few towers, 14 is quite a number. So I was curious and researched a bit about why San Gimignano has so many more towers. And guess what? Those towers used to be a symbol of power and wealth, so rich families were competing about who can build the tallest tower. And with its prime location along a Roman trading route, there were plenty of rich families, as you can imagine.
San Gimignano is small. But since it’s so pretty, it’s quite a popular stop during a Tuscany road trip. So it can get quite crowded and you better come in the morning or late afternoon to best enjoy the medieval town.
To do in San Gimignano:
Climb up Torre Grosso – A true highlight is the view across the town and its surrounding landscape from this tower.
Take the effort to queue at Gelateria Dondoli – to try the world-famous and awarded ice cream
Vino – Try the Tuscan white wine Vernaccia di San Gimignano & stop by the closeby Vineyard Teruzzi & Puthod.
It’s for good reason that anyone who’s been to Siena raves about the unique flair of this Tuscan city.
Siena! A place to enjoy La Dolce Vita, sipping coffee in one of the busy cafés. A place to marvel at medieval towers and brick monuments that make for shady alleys. And to take endless strolls through the UNESCO World Heritage historic center.
It’s not hard to get lost in Siena. But let’s be honest. This way, you will explore corners that you probably wouldn’t have found otherwise. And the way this city is built will always find yourself back in the main square, Piazza del Campo.
If you could do only one thing in Siena, then you should enjoy the view across the city’s roofs from the top at least once! Both Torre del Mangia, and the Opera della Metropolitana, are great places to do so.
On your Tuscany road trip, be aware that you’re not allowed to drive into Siena’s downtown. The fines are quite high. So look for the Italian signs that look like a red stop sign, even if your GPS wants to send you further.
To do in Siena:
Climb up the 400 stairs of Torre del Mangia – for a panoramic view across the city
Allow yourself to get lost – to take some time to look at the small details on the historic monuments, such as the animals marking which district you’re in
Take the marvelous “Porta di Cielo” tour of the dome’s roof
Visit the Piazza del Campo – a busy fan-shaped square where both locals and tourists like to spend time
You may have heard of Montepulciano before. That’s because it’s not only a Tuscan town but also a grape variety.
But before sipping its delicious wine, get enchanted by the gorgeous town.
Located on a hilltop within ancient city walls, you can only enter the town through one of two gates. But from here you get one of the best countryside views on your Tuscany road trip.
And the true magic of Montepulciano lies under the ground: An impressive, old tunnel system that used to connect the main palaces and is nowadays used as (of course!) wine cellars.
To do in Montepulciano:
Val d’Orcia & Asciano
Not far from Siena and Montepulciano you can find the iconic Tuscany road trip countryside that comes to your mind when you picture Tuscany. A picturesque, soft hillside and winding alleys framed by picture-perfect cypress trees.
This is exactly what you can find in the valley called Val d’Orcia and around Asciano.
That’s obviously what makes it of the most beautiful areas of Tuscany for many. So if you’ve got some time, spend a couple of nights in an Agriturismo in this area to slow down and breathe in the beauty of this place.
Besides, if you love wine, you will love Val d’Orcia for the popular Brunello di Montalcino grapevine.
To do in Val d’Orcia & Asciano:
Drive around – It’s all about the landscape over here, so take some time to drive from one cute village to another and stop on the side of the road whenever you catch a special view.
Montalcino – Visit the cute hilltop town
Try the delicious Brunello di Montalcino wine – to get a true taste of the area
Visit the Cipressi di San Quirico – where the traditional cypress trees are planted in a circle
It may be the most photoshopped Instagram hotspot in Tuscany, but on a cold day, a visit to the Saturnia hot springs may be a nice idea for some relaxing time. But don’t expect those empty pools you’ve seen on Insta. This place is usually packed.
After visiting quite a few towns, how about a day by the beach to calm down? Yep, Tuscany also has some charming beaches. Especially the Ligurian Coast around Livorno is quite popular for both local beach goers and tourists. I’d highly recommend Cala del Leone for a nice swim.
And while you may have heard of the island Elba, you probably didn’t know that it belongs to the region of Tuscany, right? So why not extend your Tuscany road trip with a few days on the island of Elba.
Hidden gems in Tuscany
As you can imagine, Tuscany is dotted with stunning cute towns and villages and breathtaking views. On every corner, you may find another hidden gem in Tuscany. This could be a photogenic hilltop village, a vineyard or a panoramic road.
Here are just a few lesser-visited places. But for sure, you’ll stumble upon so many more hidden gems in Tuscany during your road trip. Even when you least expect it.
Hidden gems in northern Tuscany
If you’d like to head a bit off the beaten path, Pistoia is also a cute stop. With its prime location among many pilgrims routes, also the famous Route of St. James to Santiago de Compostela passes through Pistoia.
Although it’s famous among locals for its world-renowned chocolatiers, Pistoia is one of Tuscany’s least visited towns. So grab a nice ice cream at one of the gelaterias or get some chocolate to take home for your loved ones.
Everything you’re hoping to experience in Tuscany can be found in Poppi. While it’s a small town, it offers beautiful views, an old castle, and great wine.
is a great stop for a tour and wine tasting
with incredible views.
Greve in Chianti
As the name suggests, Greve lies right in one of the most famous Italian wine regions. So it’s not only the perfect place to take in the beautiful scenery but also for a nice wine tasting.
Besides, stroll through its triangle-shaped square. If you’re there on the last Sunday of a summer month, don’t miss the organic farmers market (from March till December).
Hidden gems in central & southern Tuscany
While the area around Bolgheri is well-known for its many vineyards, driving to the small town is especially spectacular. You drive along Viale dei Cipressi – an extremely beautiful avenue of centuries-old cypresses.
Yet, fewer people actually make it to the small town of Bolgheri itself. But don’t miss it, as it’s a calm, genuine town where you can visit an old castle or sit in one of its many taverns sipping delicious wine.
To enjoy the authentic Tuscan experience, head to Volterra. This medieval hilltop town is one of the lesser-visited places on your Tuscany road trip, even though it’s not far from San Gimignano. Nevertheless, driving to Volterra is impressive, as you can spot the medieval town watching over its hill already from far away.
Over here, you will find many souvenirs made from alabaster, as the place is known for the production of alabaster.
Although it’s a bit further inland, Arezzo is also worth a visit on a Tuscany road trip. When you’re there, don’t miss taking a look at the remains of its amphitheater and climbing one of the best spots for fantastic views across the town. You can find this stunning view either on top of the clock tower Palazzo della Fraternita dei Laici or from the Arezzo Cathedral’s hilltop.
In case you’re in Arezzo on a Wednesday or a Sunday between April and October, here’s another tip: The winery I Giorni del Vino opens its doors for visitors twice a week. So, on Wednesdays and Sundays, you can take a look into a traditional Tuscan winery.
If you stay in Siena for a few days, Monteriggioni makes up for a great day trip or a nice stop during your Tuscany road trip. Overlooking the countryside, this small village (or rather castle) is a stunning little gem completely surrounded by an intact city wall. With its many towers, it looks like it’s right out of a postcard.
Colle Di Val D’Elsa
Like many Tuscan towns, Colle Di Val D’Elsa is a well-preserved medieval hilltop town. But it’s one of the more dreamy ones. With its location right between Florence and Siena, it’s the perfect countryside day trip from either of them.
This cute little town is known for two things: As Pinocchio’s creator Carlo Collodi spend several years here, many people assume that Colle Di Val D’Elsa is the birthplace of this famous child book. Besides, the fine glasses for the Chianti wine were traditionally blown here.
Enjoy the road
Even though Tuscany is full of stunningly beautiful towns, the true magic of the area is the landscape and the time on the road. A Tuscany road trip is all about enjoying the views.
So allow yourself to get lost, e.g. on the road through many scenic Tuscan villas around Asciano and Val d’Orcia.
And try not to stick to the fastest route on Google Maps, but rather take a slower, windy road through the landscape. So let the road be your destination. And feel free to stop anywhere you discover a cute village or vineyard that invites you to a spontaneous stop.
Enjoying the landscape in Tuscany
Tuscany Itinerary 7 days
7 days round trip starting and ending in Florence (suggestion 1):
Florence (2 nights) ⇨ Vinci ⇨ Lucca (1 night) ⇨ Pisa ⇨ Montepulciano (1 night) ⇨ Val d’Orcia / Asciano ⇨ Siena (2 nights) ⇨ San Gimignano ⇨ back to Florence
Florence: The capital of Tuscany is a great start for your trip, especially if you arrive by plane. After 2 days in Florence, you can pick up your rental car.
Florence ⇨ Vinci
Start your Tuscany road trip with a short distance and a day trip to Vinci.
Vinci ⇨ Lucca
After a morning/afternoon in Vinci, head on to Lucca where you can enjoy dinner, spend the night, and use the next morning to explore.
Lucca ⇨ Pisa
In case you feel like seeing this tourist magnet, you can stop in Pisa, as it’s quite close to Lucca.
Lucca/Pisa ⇨ Bolgheri
After spending your morning in Pisa, be ready for a longer drive down the E80 along the coast. Feel free to spontaneously stop wherever you feel like. A great stop is Bolgheri. Don’t take the highway, because the idyllic E80 is so much more fun.
Bolgheri ⇨ Montepulciano
Once you turn inland after your stop in Bolgheri, it’s time for the typical Tuscan countryside. This route is one of the most beautiful parts of your Tuscany itinerary.
Montepulciano ⇨ Siena
Spend the night and a relaxed day in Montepulciano, before driving to Siena. I’d suggest driving through Val d’Orcia, Val d’Asso or Asciano, as this area is extremely beautiful. Then, spend two nights in Siena, as there’s so much to see.
Siena ⇨ San Gimignano
On your way back north, San Gimignano is the perfect stop, as it’s a small town.
San Gimignano ⇨ back to Florence
In case you fly back home from Florence, the last part of your road trip takes you back to where you can return your rental car. You could add a stop in Greve in Chianti, if you’d like to.
If you came all the way with your own car, why not add another few stops such as Volterra or Arezzo on your way back north?
Map of 7-day Tuscany itinerary suggestion 1 (click for interactive map)
7 days round trip starting and ending in Florence (suggestion 2):
Just as the suggested route above, you can take many Tuscany itineraries starting and ending in Florence. Here’s another suggestion:
Florence (2 nights) ⇨ Greve in Chianti ⇨ Arezzo (1 night) ⇨ Montepulciano ⇨ Val d’Orcia (1 night) ⇨ Montalcino ⇨ Siena (2 nights) ⇨ Colle di Val d’Elsa ⇨ San Gimignano (1 night) ⇨ back to Florence
Florence: Just as in the first suggestion, start your Tuscany itinerary with two days in beautiful Florence.
Florence ⇨ Greve in Chianti
Pick up your rental car and drive down 45 minutes to the wine region Greve in Chianti.
Greve in Chianti ⇨ Arezzo
After spending your morning or afternoon in Greve, head on to Arezzo where you can enjoy dinner, spend the night, and use the next morning to explore.
Arezzo ⇨ Montepulciano
Now, it’s time to head further south with a stop in Montepulciano.
Montepulciano ⇨ Val d’Orcia
After a morning or afternoon in Montepulciano, dive deep into the Tuscan landscape around Val d’Orcia where you spend another night with stunning surroundings.
Val d’Orcia ⇨ Montalcino
Beautiful Montalcino is the perfect stop-over to spend a few hours before driving to Siena.
Montepulciano ⇨ Siena
Spend two nights in gorgeous Siena, and soak up this beautiful gem.
Siena ⇨ San Gimignano
On your way back north, the small town San Gimignano is the perfect stop.
San Gimignano ⇨ back to Florence
In case you fly back home from Florence, the last part of your road trip takes you back to where you can return your rental car.
If you came all the way with your own car, you could add another stop such as Volterra or even Lucca on your way back north.
Map of 7-day Tuscany itinerary suggestion 2 (click for interactive map)
Tuscany Itinerary 10 days
10 days round trip starting and ending in Florence:
My first suggestion would be to take one of the 7 days routes and add more stops, such as:
Suggestion 1 (based on the 7 days itinerary):
Florence (2 nights) ⇨ Vinci ⇨ Lucca (1 night) ⇨ Pisa ⇨ add Bolgheri & a beach stop (1 night) ⇨ Montepulciano (1 night) ⇨ add Val d’Orcia (1 night) ⇨ Siena (2 nights) ⇨ add Monteriggioni or Colle di Val’dElsa ⇨ San Gimignano (1 night) ⇨ back to Florence
Suggestion 2 (based on the 7 days itinerary):
Florence (2 nights) ⇨ Greve in Chianti ⇨ Arezzo (1 night) ⇨ Montepulciano ⇨ Val d’Orcia (1 night) ⇨ Montalcino ⇨ Siena (2 nights) ⇨ Colle di Val d’Elsa ⇨ San Gimignano (1 night) ⇨ add Bolgheri (1 night) ⇨ add Pisa ⇨ Lucca (1 night) ⇨ add Vinci or Pistoia ⇨ back to Florence
Florence (2 nights) ⇨ Poppi ⇨ Arezzo (1 night) ⇨ Montepulciano (1 night) ⇨ Val d’Orcia/Asciano (1 night) ⇨ Siena (2 nights) ⇨ Monteriggioni ⇨ San Gimignano (1 night) ⇨ Volterra ⇨ Lucca (1 night) ⇨ back to Florence
Tuscany itinerary with one base
Another great option to see Tuscany is to book a beautiful house or room in an Agriturismo somewhere in the countryside as a base and do day trips. Everything is close by within Tuscany.
You could also choose two places – one in northern Tuscany for the first five days and then another base in southern Tuscany where you can spend the last days of your trip.
A complete map of Tuscany places to see (click for interactive map)
Good to know
What’s the best time to visit Tuscany?
For a relaxed Tuscany road trip, spring and autumn are perfect. In summer, the narrow medieval town centers get quite crowded and really hot as well. From April till June you’ll get bright, sunny days but also September and October are perfectly warm.
We spent long days by the sea in June while it was also not too hot to go sightseeing and to drive from town to town.
How to get around Tuscany?
There’s one simple best way to get around Tuscany: By car. If you can’t drive there with your own car, I highly recommend getting a rental car.
The bus and train connection in Italy is not bad, however you won’t be able to reach many of the gorgeous Tuscan villages and viewpoints by public transport. Especially if you’d like to see some hidden gems in Tuscany.
Especially the freedom and flexibility a car gives you are spectacular. This way, you can stop by the side of the road to enjoy a view or spontaneously visit a beautiful vineyard.
If you fly to Florence and get a rental car, I suggest picking it up a few days after you land. Because within the city you definitely won’t need a car.
How much time do you need for a Tuscany road trip?
Well, I’d say you can spend as much time in Tuscany as you have. You can pick 2-3 stops and spend a few days there or opt for a 7-day Tuscany itinerary, but you can also easily extend it to 10 days or even a 2 weeks Tuscany road trip or more. It won’t get boring, I promise.
I’ve got a few suggested routes for a Tuscany itinerary for different lengths. To be able to see a few different places, I’d suggest a minimum Tuscany itinerary of 7 days. Two weeks is perfect to get a nice overview of northern and southern Tuscany. Keep in mind that the longer route is always the more beautiful route over here.
Where to start your Tuscany road trip?
If you can’t get to Italy by car from your home, the best places to fly to are Florence or Pisa. You can also fly to Bologna which is a bit further north (and a beautiful city as well, but not part of Tuscany but the capital of the Emilia-Romagna region). From here, it’s just a two-hour drive to Tuscany.
Where to stay in Tuscany
Basically, you have two options to design your Tuscany road trip. Either you stay in different places and do a proper roundtrip, or you book one base and do day trips. Both are possible and have their own upsides.
When you do a roundtrip, it’s easier to see more and usually you spend less time on the road (as you don’t have to drive back every day). With a base, you don’t have to check into different guesthouses and pack again every few days. On the other hand, it might be quite a long drive to some destinations.
What to be aware of?
As you’re on a Tuscany road trip by car, you should consider a few things when it comes to driving in Italy. In many cities, you’re not allowed to enter the town center by car and you get fined. So don’t make the mistake and try to drive all the way to the center. Keep your eyes peeled for the signs (they look similar to red stop signs).
The best is to always check for a parking lot a bit outside of the center before you start driving to your next destination. Plus: Often there is free parking a bit further from the center from where you can still walk.
Sustainable travel in Tuscany
Being surrounded by such a stunning landscape, we have to talk about how we can protect it.
First, the type of accommodation you choose can make a huge difference. Please avoid all-inclusive hotels, because they cause ridiculous amounts of waste.
And well, you want to spend most of your time outside anyway, so why spend such a huge sum on an expensive hotel which boxes you in?
So instead, stay at local guesthouses (often called “Agriturismo” in Italy) or eco-lodges.
And during the day: Go out, explore and munch on the local food!
That brings us to the next part. When you eat out or buy products at a local market, and cook yourself, you support the locals. That’s awesome because your money goes right to the Tuscans instead of international companies.
Also, try to avoid unnecessary waste by bringing your own tote bag for shopping and a food container, and your own cutlery for your snacks. In case you buy something that causes litter, make sure to take it with you when you leave and properly ditch it into bins where you can separate the trash. This way, you can make sure that it gets properly recycled. Many parking areas along the beaches in Tuscany have trash bins with waste separation.
One of the largest polluters is bottled water. So avoid buying plastic bottles. Instead, bring your own water bottle. There are many public water refill stations in Tuscany. Just search for “Casa Dell’Acqua” or “drinking water fountain” in Google Maps. Those are stations where you get free filtered water or sometimes for 5 cent/liter.
Besides, you can also bring your own water purifier, such as a Grayl water bottle. This way, you can take water from any tap and filter it yourself.
Tuscany – a wrap-up
Tuscany in three words: wine grapes | cypresses | medieval towers
Did you know? Many simple Tuscan table wines belong to the highest quality Italian wines (so-called “Supertuscans”)
Favorite photo spot: Honestly, all over Tuscany you stumble upon random but perfectly beautiful photo spots. Just grab a car, go out and explore and you’ll find them yourself.
Favorite food: Pasta on every corner (mmmhh the Cacio e Pepe pasta)
Can’t miss: Taking the slower route. Don’t listen to your GPS taking you to the highway. Always choose the countryside road. You won’t regret it!
Did you ever do a Tuscany road trip? How was your experience? And do you have any other recommendations for a Tuscany itinerary? Share your tips in the comments below!