Tuscany is a dream destination with incredible thermal baths, enchanting vineyards, and stunning hilltop towns. Yes, you can explore some major cities and towns using public transportation.
However, to get off the beaten path and enjoy everything the region has to offer, plan a 10-day Tuscany road trip itinerary.
Trust me, I’ve visited this part of Italy many times and can assure you that this is the best Tuscany road trip itinerary out there.
You’ll start in Florence since the city has an international airport and a wide array of rental cars available (aka a good selection of cars and agencies that are open late).
Next, you’ll continue to Montepulciano, Siena, San Gimignano, Volterra, Lucca, and end in Pisa.
Overall, this Tuscany Italy road trip will give you an overview of the region without having you rush around from one place to the next.
Just do yourself a favor and do NOT get a big car. Roads in Italy are smaller than the ones in the States. So, it’s easy to get stuck on a tiny road or under a quaint bridge while driving through Tuscany.
Also, be prepared for aggressive drivers, lots of beeping, and watch your speed. Remember, the speed limit in most towns is 50km/h.
You won’t see a lot of signs about the speed, but there are speed cameras EVERYWHERE.
They will snap a pic of you and give you a ticket to take home with you. Been there and done that and it is very much not un-fun.
Other than that, just enjoy you time in this amazing part of Italy. Tuscany is truly unlike any place I have ever been and the best way to enjoy it is with this road trip to Tuscany.
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Read This Before Renting a Car in Tuscany
Planning a road trip through Tuscany? If so then you’ll need to rent a car. After all, a road trip is kind of hard to do without a car.
So, if you don’t know where to rent a car in Tuscany then try Discover Cars. It is the BEST car rental company in Tuscany.
I’ve been a customer for years and this is the only company I rent from because I have had nothing but good experiences with them.
I like Discover Cars because they have amazing rates and a comprehensive (but affordable) Full Coverage Policy.
Plus, they allow cancellations up to 48 hours in advance, which is great if something unexpected comes up.
So, head to the Discover Cars website now and put in your travel dates, along with your pick-up location.
Next, filter the ratings so that you only see companies with 7+ stars out of 10 or better. Yeah, you don’t want to rent from a super cheap company with terrible reviews.
After all, these companies like to sneak in additional fees that make them very un-cheap once everything is said and done.
Instead, try and rent from a well-reviewed company that is known for excellent service and reasonable prices.
Best Tuscany Road Trip Itinerary
Stop 1: Florence
Florence, like Rome, is a vibrant city with incredible architecture, world-class art, and next-level awesome food. So, spend at least 2 days in Florence, 3 days if you can manage it.
I would also recommend getting your Tuscany rental car AFTER you explore this city, preferably from the airport. This way you can avoid driving in the city which is a REAL pain in the ass.
Besides, you do not need a car in Florence. So, it’s kind of pointless to spend money on a car that you won’t even use.
Start your time in Florence with a visit to the Boboli Gardens. Afterward, explore the Villa Bardini Gardens, Pitti Palace, and Ponte Vecchio before catching the sunset at Piazzale Michelangelo.
Get up early the next day and go museum hopping. Visit the Accademia Gallery (say hi to David for me), The Duomo (Baptistry/Bell Tower), the Central Markets for lunch, and the Uffizi Gallery.
End the day at the Piazza della Signoria and call it an early night. This way you can pick up your rental car in the morning.
No, you won’t be able to see EVERYTHING in Florence. But, you’ll enjoy the major highlights before heading out to Tuscany.
Expert Tip: If you’re short on time you could also try one of the best wine tours of Tuscany from Florence or try some of the best wine tours around Florence while you’re here.
I would also pre-book ALL of your tickets for major attractions in Florence since these places are VERY popular and lines can be exceptionally long.
Where to Stay: YellowSquare Florence (budget), Palazzo Testa (mid-range), and Borgo Signature Rooms (luxury).
Number of Nights: Plan to spend at least two FULL days in Florence. So, you may need to spend two or three nights depending on when you arrive in the city.
Stop 2: Montepulciano
Get up early and enjoy a one-and-a-half-hour drive (2 hours if you pick up your car at the airport) to Montepulciano.
Upon arrival, settle into this Medieval, walled town with sweeping views of Val d’Orcia and Val di Chiana.
While you’re here, stroll along the main street of II Corso, check out Piazza Grande, see the Duomo, explore the church of San Biagio, and take in views from the tower at Palazzo Comunale (town hall).
Afterward, sample some Vino Nobile di Montepulciano during a wine tasting at Salcheto. You can also head to Pienza to try some amazing pecorino and pici alle briciole (pasta with breadcrumbs).
Alternatively, relax the day away at the San Filippo Thermal Springs (Bagni San Filippo) since this is one of the few natural hot springs in the region that is free, totally natural, and open to the public.
For a more luxurious experience, visit Chianciano Terme instead. This chic spa sits 15 minutes outside of town and is filled with whirlpools, saunas, mud baths, ice baths, Turkish baths, etc.
You can also book high-end treatments, like facials and massages, while you’re here.
Finally, explore the Val d’Orcia. It’s a designated UNESCO World Heritage Site that is known for its incredible beauty.
This region is also home to the town of Montalcino. Taste some Brunello di Montalcino (one of the best wines in Italy) here before doing a tour of Castello Banfi I borgo (Europe’s largest wine producer).
Where to Stay: La Terrazza Di Montepulciano (budget), La Dimora nel Corso (mid-range), and La Locanda Di San Francesco (luxury).
Number of Nights: Spend at least two nights here.
Stop 3: Siena
A quick hour’s drive from Montepulciano is Siena, a famous city in central Tuscany known for its Medieval brick buildings.
It is a great place to spend the next two days of your Tuscany road trip itinerary since the entire city center is a UNESCO World Heritage Site.
Highlights include Piazza del Campo, Palazzo Pubblico (a Gothic-style town hall), and Torre del Mangia.
This impressive tower dates back to the 14th century and offers sweeping views of the surrounding area if you can manage to climb up the 400 steps to the top.
Afterward, explore the Duomo (Cathedral of Santa Maria Assunta) and check out the museum at Santa Maria della Scala since it is one of the oldest hospitals in the country.
You can also visit the Basilica of San Domenico and try local dishes like pici all’aglione (pasta with tomato sauce), panforte (spiced honey cake), and ricciarelli (local cookies).
Where to Stay: Eleroom (budget), La Terrazza Sul Campo (mid-range), and Palazzetto Rosso (luxury).
Number of Nights: Spend two full nights here.
Stop 5: San Gimignano
Drive fifty minutes down the road to the hill town of San Gimignano. Encircled by ancient walls from the 13th, this is where you’ll find the Piazza della Cisterna.
It is a beautiful square, with a triangular shape, that is surrounded by stunning medieval homes. You can even enjoy some world-famous gelato from Gelateria Dondoli while you’re here.
Other must-sees include the Torre Grossa for epic views of the region and the Duomo di San Gimignano. This church from the 12th century features amazing frescoes by Ghirlandaio that are stunning to behold.
Afterward, enjoy some incredible contemporary art at Galleria Gagliardi, grab lunch at Le Vecchie Mura (get the bruschetta and the pici), and explore the Parco della Rocca and Cotadel.
You can also learn a bit more about the town’s unique history at Palazzo Comunale.
Just don’t leave without sampling the town’s famous Vernaccia since it is known for being “the first Italian DOCG wine.”
My favorite place to grab some wine is at La Vecchia Nicchia di Alessandro Pieragnoli Enoteca since the bruschetta is AMAZING.
Where to Stay: Affittacamere Mainardi 16 (budget), La Fornace Di Racciano (mid-range), and Podere Bellavista (luxury)
Number of Nights: Spend two nights here.
Stop 6: Volterra
Get up early today since there will be a lot of driving if you want to complete this road trip in Tuscany. From San Gimignano, the drive to Volterra will take around 40 minutes.
It’s a smidge out of the way but is worth the trip since this ancient walled town is home to the Palazzo dei Priori.
This historic town hall sits inside the Piazza dei Priori and has amazing frescoes as well as a bell tower (Tower of the Little Pig) that you can climb for awesome views of the area.
Afterward, stop by Volterra Cathedral since this Romanesque building has a beautiful marble entrance and an enchanting, coffered ceiling.
Just opposite the Duomo, you’ll also find the Baptistery of the Cathedral which has an octagonal shape and dates back to the 13th century.
If you have time, you can also visit the Guarnacci Etrurian Museum and a Roman Theater complex with baths from the 3rd century.
Stop 7: Lucca
After spending a few hours in Volterra, drive an hour and fifteen minutes to Lucca. I love this town because it has well-preserved 16th-century walls and lovely cobblestone streets.
It’s a great place to walk around since there are a ton of tree-lined streets. Plus, you can actually walk along the city’s ancient walls.
If you want, you can even visit the Casa di Puccini and see where the famous opera singer was born.
Other cool things to do include a visit to St. Michael’s Church to see the Ilaria del Carretto’s Tomb/Volto Santo, a walk through Piazza dell’Anfiteatro, a climb up Torre Guinigi, and a trip to the National Art Gallery.
You won’t be able to see EVERYTHING this amazing town has to offer in a day, but you will get a feel for this place and can always extend your stay if you’re not really interested in Pisa.
Where to Stay: Il Vicolo (budget), Residenza FillAnfi (mid-range), and Hotel Alla Corte degli Angeli (luxury).
How Many Nights: Spend one night here. You can spend two if you’re not into Pisa.
Stop 8: Pisa
From Lucca, it’s a quick thirty-minute drive to Pisa. TBH, Pisa isn’t my favorite place in Italy.
It’s super crowded and isn’t as beautiful as some of the other stops on this itinerary.
However, it is home to the world-famous Leaning Tower of Pisa, which is why I added it to this 10 day Tuscany road trip itinerary the last time I did a solo trip in Italy.
You probably only need a day in Pisa MAX and a half day if you’re in a hurry. You could also skip Pisa entirely if you are short on time and just head back to Florence.
If you do decide to visit, stop by the Square of Miracles and see the one and only, Leaning Tower of Pisa. The Pisa Cathedral is also right here and is truly stunning.
If I’m honest, the Leaning Tower of Pisa was way more beautiful than I expected, even if there were selfie-stick-wielding tourists everywhere.
Just be sure to book your ticket well in advance if you want to go inside and climb to the top of the tower.
If you have time and are visiting Tuscany in September (or at the start of fall in Tuscany when it’s still warm) head to the Marina di Pisa and hit the beach.
Otherwise, head to Camaiore or Pietrasanta to enjoy some of the best hikes in Italy.
Expert Tip: Depending on what you want to do, you can drop your car off in Pisa or head back to Florence.
The drive to the airport in Florence will take about an hour, but it will be cheaper if you drop off/pick up your rental car from the same place.
Driving back to Florence may also be a better option if you have a flight leaving from Florence early in the day.
Map of One of the Best Road Trips in Tuscany
Conclusion
That just about wraps up my pick for the best Tuscany road trip itinerary. What I love about this trip is that is very customizable.
So, if you have more or less time in Tuscany, you can easily adjust this itinerary to suit your needs. I mean, if you are short on time you can skip Pisa and head straight back to Florence.
You could also spend one less day in Montepulciano and then continue with your trip from there.
All in all, this itinerary is great if you want to move at a relaxed pace and see some of the best towns in Tuscany.
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