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Going on a scenic road trip in Tuscany is absolutely a bucket list experience! With medieval hilltop towns, rolling hills, gorgeous vineyards and even enchanting hot springs, this region is one of the best places to go in Italy.
Everywhere we went in Tuscany we fell in love, so we know you will too! We’ve organized our favorite towns into a detailed itinerary for how to spend 10 days in Tuscany. That said, you can certainly condense this route to fit a shorter time frame if you’re tight on time.
>> Read: Perfect 2 Week Italy Itinerary for how to visit Tuscany in 2 days
Best towns to visit on your road trip in Tuscany
- Florence
- Greve in Chianti
- Siena
- Asciano
- Montepulciano
- Saturnia
- San Gimignano
10 days in Tuscany – road trip itinerary
Day 1-3: Florence
Certainly no trip to Tuscany is complete without visiting the capitol of the region, Florence. Florence is also the closest international airport to the towns on this road trip in Tuscany, so it’s a great starting point.
Start your trip by flying into Florence (FLR) and spend your first three days enjoying the gorgeous Renaissance architecture and art. While Florence is bigger than the rest of the towns on this Tuscany itinerary, it still maintains a quaint vibe and is rich in history, romance and INCREDIBLE food.
>> For how to spend your 3 days here, read the 15 BEST things to do in Florence!
Note: since Florence is not car friendly, don’t pick up your rental car until day 4.
Day 4: Florence to Greve in Chianti
Since the best place to rent a car in Florence is at the airport, head to the Florence airport on the morning of day 4. In order to get to the airport either take a taxi or take the T2 tram from the city center.
After you pick up your rental car, you’re ready to start your official road trip in Tuscany! Begin by driving to Greve in Chianti, which is only about a 45 minute drive.
The town of Greve is located in one of the most famous wine regions of Italy, the Chianti region. Once you arrive, spend the rest of the day enjoying the beautiful medieval town and taking in the scenery.
If you’re looking for a quaint and quintessential Tuscan experience, stay overnight amidst the rolling hills at Cascina Dè Fagiolari.
Day 5: Greve in Chianti
Spend your second day in Greve taking a bike tour, visiting the different castles in the Chianti region and, of course, going wine tasting.
Finally after a great day of activities, finish the day with an authentic Italian cooking class. Because of how unique and fun it was, the cooking class we took at Cascina Dè Fagiolari became one of our favorite experiences during our 6 weeks in Italy!
Spend one more night in Greve after you finish your cooking (and eating!) experience.
Day 6: Greeve to Siena
On day 6 plan to leave Greve at your leisure and head to Siena, which should take about an hour. The historic center of Siena is a UNESCO site and the town is one of the most visited places in Italy.
Once you arrive, spend the day walking around the medieval city and marveling at the architecture. Two must-sees in the area are Piazza del Campo and Duomo di Siena (Siena Cathedral).
Certainly you can’t miss the ornate details and black and white stripes of the Duomo di Siena. While this cathedral was planned to be the largest basilica in the world, when funds ran out and the plague hit the city the project had to be cut short.
Piazza del Campo is one of the most renowned medieval squares in Europe and still plays a prominent role in the town. Twice a year each year they hold the Palio di Siena horse race on the edges of the square.
After your sightseeing, make your way to Osteria Cice for an AMAZING and authentic Italian meal.
Certainly stay a night in Siena – we had an amazing stay at BnB Paolina which impressed us with the perfect location and unbelievable balcony views!
Day 7: Siena to Asciano
While Siena is known for its architecture, Asciano is known for its natural beauty and landscape. This area is one of the most picturesque and scenic parts of Italy, so don’t forget your camera!
Spend your day in Asciano enjoying the quiet town, hiking one of the dozen different routes through the Tuscan hills and, above all, taking in the scenery.
Another great experience on your road trip through Tuscany is staying the night at an authentic Italian farm stay, Agriturismo Baccoleno. Because of the winding road lined with trees and the unbelievable views, this place is also home to the best photo spot in town.
Day 8: Asciano to Montepulciano
On day eight drive 40 minutes to Montepulciano, another medieval town which is most famous for Vino Nobile red wine. The town is situated on a hilltop and is located within ancient city walls, so you are only able to enter through one of the two main gates.
Even more impressive than the history you find above ground in Montepulciano, is the history you find below the historic center in the underground city!
While back in the day these caves and tunnels connected the main palaces, now they are used as unique wine cellars.
As a result, you can now tour the underground wine cellars with a free tasting at wine shops around town. Because of the sweet family and generous tasting pours, we’d highly recommend the free tour and tasting at Azienda Agricola Ercolani!
Another thing not to miss in Montepulciano are the striking sunrises and sunsets which are truly one of a kind!
When looking for a place to stay in Montepulciano, definitely check out Villa Cicolina! Our stay here was perfect and you certainly can’t beat the view of the Tuscan hills from the infinity pool.
Day 9: Montepulciano to Saturnia
While at 2 hours this is one of the longest stretches of driving on your road trip in Tuscany, rest assured that the destination is absolutely worth it! Saturnia is home to the most enchanting thermal baths, which are certainly one of our favorite places in Italy.
As a result of water flowing down over centuries, layers of bright blue thermal pools have formed amidst the rolling hills of the area. The hot springs maintain a temperature of 37.5C/99F year-round and people believe that they have healing properties, just another reason this is a must-do on your road trip through Tuscany!
Once you finish your drive, head straight to Terme di Saturnia to enjoy the FREE baths!
>> For where to stay in Saturnia and everything you need to know before visiting the thermal pools, read our Complete Guide to visiting Saturnia Hot Springs!
Day 10: Saturnia to San Gimignano and back to Florence Airport
If you’re anything like us, you’ll want to go for another dip in the hot springs before you head out. Start day 10 early with another nice trip to the thermal baths, and then enjoy a shower and breakfast at your accommodation before hitting the road.
Because Saturnia is the most southern destination on your road trip in Florence, driving back to the Florence airport from here will be your longest trek (3.5 hours total). However, you can break up the drive with a stop in the historic town of San Gimignano.
San Gimignano is the quintessential Italian hilltop town and is most famous for its ancient skyline of towers. While you’re here, stroll through the historic center within the ancient city walls and take in the panoramic hilltop views.
Pro tip: we had an amazing lunch overlooking the Tuscan landscape at Sosta Sulla Francigena. We also indulged in best gelato we found in Italy at Il Chioschino di Sangi!
Finally, after you spend some time in San Gimignano, it’s time for the final 1 hour of your drive back to the Florence airport. Although you’ll certainly leave Tuscany wanting more, it’s time to say goodbye and take a lifetime’s worth of beautiful memories with you!
Tuscany road trip route
| Start and end points | Driving distance | Driving time |
| Florence airport to Greve in Chianti | 24 mi (39 km) | 42 minutes |
| Greve in Chianti to Siena | 28.5 mi (46 km) | 1 hour |
| Siena to Asciano | 19 mi (31 km) | 40 minutes |
| Asciano to Montepulciano | 22 mi (36 km) | 40 minutes |
| Montepulciano to Saturnia | 58 mi (93 km) | 2 hours |
| Saturnia to San Gimignano | 96 mi (155 km) | 2.5 hours |
| San Gimignano to Florence Airport | 41.5 mi (67 km) | 1 hour |
| Total road trip | 290 mi (468 km) | 8.5 hours |
Road trip in Tuscany map
Below is a map of the route for your road trip in Tuscany so that you can visualize your 10 day plan. Click the ‘star’ next to the map name in order to save this map under “your places” in Google Maps.
Tips for your Tuscan road trip
- If you want to visit other places in Italy on your trip, check out the Best places to visit in Italy and the Ultimate 14 day Italy Itinerary!
- Coming from the US all we needed was our normal US driver’s license, but you should check with the rental company beforehand to see if they require an international license.
- When you’re renting a car, make sure to specify if you want manual or automatic.
- Because they drive on the right side of the road and have nicely paved highways, driving in Italy is pretty straightforward for those coming from the US.
- Most of the streets in these Tuscan towns are narrow and the signs make it unclear where cars are allowed, so we recommend finding a place to park on the perimeter of the town and then exploring by foot.
- Italy does not require a vignette pass like many European countries do, however the highways are toll roads where you pay for the distance you drive. Because of this, make sure to hang onto your ticket so you aren’t over charged when exiting the highway.
Planning to travel more throughout Italy? Make sure to check out our other Italy Travel Blogs!
- The perfect Florence Day Trips
- Instagram-worthy spots in Florence
- Cinque Terre complete guide
- 12 Must-Sees in Positano, Amalfi Coast
- Amalfi Coast Instagram spots
- 8 Must-See places in the Dolomites mountains
Enjoy your trip!
Kylie & Scott
(If you liked this article or have any questions, please comment below! And make sure to follow along on Instagram @LoveHardTravelOften)
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