Where to Drive To In Tuscany

Which towns in Tuscany should you visit? Well, since my goal was to see the most scenic drive in Tuscany (see below!) from Florence, I had to narrow it down based on my #1 location which was in the Val’Dosay region by the town of Asciono. When I was researching towns in Tuscany to see, there are so many to choose from, here are the top towns in Tuscany to consider seeing along the way:

• Lucca: The Walled City. Lucca is a charming walled city that is known for its well-preserved Renaissance architecture. The town’s historic center is pedestrianized and is a joy to explore on foot or by bike. you can walk along the city walls and enjoy stunning views of the surrounding countryside. Lucca is also known for its delicious food and is home to some of the best restaurants in Tuscany! I really was considering visiting but unfortunately, we did not make it this time.
• Siena: Siena is a charming medieval town that has preserved much of its historic architecture and art. The town’s centerpiece is its stunning cathedral, the cathedral is a must see! You can explore the town’s winding streets and admire its beautiful architecture, including the Palazzo Pubblico and the Torre del Mangia.
• San Gimignano: San Gimignano is a beautiful medieval town and it’s interesting because nowhere else in Italy has as many towers.
• Montepulciano: Home of the famous red wines of Italy, Vino Nobile di Montepulciano. The town’s historic center is filled with beautiful palaces and churches, including the Palazzo Comunale and the Cathedral of Santa Maria Assunta. It’s a beautiful town that is perched up high on a hill, allowing you to see breathtaking views of the Val D’orcia region.
• Pienza: Pienza is like picture perfect postcard. Pienza is a small town that was built in the 15th century as a Renaissance utopia. The town’s historic center is a UNESCO World Heritage Site and is known for its stunning architecture and beautiful views of the surrounding countryside
• Montalcino: If you’re a vino, and red wine is your go-to, then Montalcino is not to be missed! It is a charming hilltop town that is known for its production of the famous Brunello di Montalcino wine.
• Asianco: A Hidden Gem in Southern Tuscany. Located in the southern part of Tuscany, Asciano is a small and charming town that is often overlooked by many. However, in my opinion, it has one of the most scenic drives in Tuscany, with beautiful views of the surrounding countryside and Cyper lines trees with a small medieval town in the background (the photo above!). The town is home to several excellent restaurants that serve local specialties such as pici (thick, hand-rolled pasta) and wild boar stew. Additionally, Asciano is known for its olive oil production, a great gift to bring back for friends and family.

TIP: A lot of these towns are small and can be seen in less than an hour. Parking is very limited in these small Tuscan towns. As most of them, you cannot drive through the town, and depending on the day and time of year, your time gets eaten up searching for parking.

Because I had limited time in Tuscany, I had to narrow the list down to 4 towns on the way to Asciano. So the route I decided on was to the famous region of Val D’orcia in Siena, Pienza, Asciano, and Bagni San Filippo and give each at least a little of the time they deserve and then back to Florence to return the car. I could have driven the car to Rome but decided it was faster to take the train from Florence and less traffic to deal with in Rome.

 When is the best time to drive in Tuscany? I went in May during spring in Italy. It’s one of the most beautiful times to drive through Tuscany because of the beautiful green colors at this time of year – which most would prefer to the sunburned yellows in summer.