Five Unexpected Places to Stop on a Drive from Castellina Scalo, Tuscany to San Dalmazio, Tuscany

Italy is known for its stunning countryside, rolling hills, and charming towns. A drive through Tuscany is no different, with breathtaking scenery that will take your breath away at every turn. From Castellina Scalo to San Dalmazio, this drive is one of the most picturesque in the country. It takes around two and a half hours to complete, but with so much to see and do, it's worth taking your time and making a few unexpected stops along the way.

Halfway Point: Casole D'elsa, SI

Before diving into the five unexpected places to stop on this drive, it's worth mentioning the midway point: the charming hilltop town of Casole D'elsa. This medieval village is perched high up on a hill and offers unparalleled views of the Tuscan countryside. With its narrow, winding streets and historic buildings, Casole D'elsa is a must-visit for anyone driving through Tuscany. Be sure to stop at one of the local cafes in the town square for a classic Italian espresso and take in the stunning surroundings.

1. Montescudaio

Montescudaio is a small hamlet that's easy to miss if you're not looking out for it. This medieval village is home to just a few hundred residents, but it's worth stopping to explore the tiny streets and alleys that lead to the town's main piazza. The highlight of Montescudaio is undoubtedly the views. From its position atop a hill, you can see all the way to the coastline on a clear day. Be sure to try some of the local olive oil, which is some of the best in the world.

Favorite food to eat: Bruschetta with tomatoes and local olive oil.

2. Bolgheri

While Bolgheri is known for its world-class wines, there's more to this charming town than just its vineyards. Bolgheri is famous for its cypress tree-lined avenue, which is truly a sight to behold. The avenue is over five kilometers long and leads to the town's main square, which is a great place to stop for a coffee or a glass of wine. The town is also home to a fantastic gelateria, so be sure to indulge in some of the local scoops.

Favorite food to eat: A glass of Bolgheri wine and a cone of gelato.

3. Suvereto

Suvereto is a picturesque medieval village that's easy to miss if you're not looking out for it. This charming town is famous for its olive oil, which is some of the best in the region. Be sure to take a stroll through the town's narrow streets to soak up the historic architecture. The highlight of Suvereto is undoubtedly the views, which stretch out over the valley below. It's a great place to stop for a picnic lunch, with plenty of local stores selling fresh bread, cheese, and cured meats.

Favorite food to eat: A slice of pizza from La Piazzetta del Gusto.

4. Massa Marittima

Massa Marittima is a small town that's packed with history and culture. This medieval village is home to some of the most impressive architecture in the region, with stunning buildings dating back to the 13th century. The town is also famous for its festivals, which take place throughout the year. Be sure to stop at the Cathedral of San Cerbone, which boasts stunning frescoes and a beautiful interior.

Favorite food to eat: A slice of pizza from Pizzeria Al Pomo D'oro.

5. Volterra

Volterra is one of the most popular towns in Tuscany, and it's not hard to see why. This ancient city is perched high up on a hill and offers stunning views of the surrounding countryside. The town is famous for its alabaster, which is a type of stone that's used to make sculptures and other decorative items. Be sure to stop at the alabaster workshops to see craftsmen at work. The town is also home to some fantastic restaurants, so be sure to indulge in some of the local cuisine.

Favorite food to eat: Truffle pasta from Osteria da Nando.

Conclusion

Driving through Tuscany is a once-in-a-lifetime experience, and this route from Castellina Scalo to San Dalmazio is no exception. By taking some unexpected stops along the way, you'll be able to get a true sense of the region's culture and history. From charming hilltop towns to stunning vineyards and olive groves, there's something for everyone on this route. So if you're looking for an epic road trip through one of the most beautiful regions of Italy, be sure to add this route to your list.