Tuscany Hill Towns Road Trip

Photo by Martha Bakerjian

Explore Tuscany's picturesque medieval towns perched on hills above vineyards and olive groves

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Tuscany is known for its picturesque medieval hill towns that dot the region. Although most hill towns can be reached by public transportation, they are best explored on a road trip by car. Driving inside the historic centers is restricted so park in a parking lot outside the center.

This itinerary takes you to 6 of Tuscany’s top hill towns and can be done in 4 days, although longer is better, especially if you want to add on other sights.

Siena, Classic Tuscany Hill Town

Siena is Tuscany’s most well-known hill town and its largest – about 4 miles of walls surround it’s historic center. Since it’s centrally located and has plenty of restaurants and hotels, it makes a good base for visiting the smaller towns. It’s a pleasure to wander through the medieval streets in the evenings when the tour groups have gone.

Siena is known for its large fan-shaped main square, Piazza del Campo or il Campo, where the Palio horse race is run two times each summer. On one side of the piazza are the Gothic town hall and bell tower, Torre del Mangia, that you can climb for great views.

Most of Siena’s monuments date from the late 13th to 14th centuries. The 13th century Gothic cathedral, or duomo, is the top must-see sight. Included in the cathedral complex are the Piccolomini Library covered with frescoes, the crypt, the 14th century Baptistery, and a museum with art works.

There’s a lot to see so plan to spend at least a full day in town. See the highlights with our 1 day Siena itinerary.

San Gimignano and Volterra

Northwest of Siena, these two towns can both be visited in the same day if you’re traveling by car.

San Gimignano is known for its concentration of medieval towers, making its skyline visible from miles away. The historic center is small and can easily be seen in a couple of hours.

Volterra, about 30 kilometers southwest of San Gimignano, is larger but can also be visited in half a day. There are usually fewer tourists here too. Volterra’s sights span a few thousand years and include Etruscan ruins, a Roman theater and forum, and many medieval buildings including the 13th century Palazzo dei Priori, Tuscany’s oldest town hall.


Cortona, to the east of Siena, is the setting of the book and movie, Under the Tuscan Sun. It’s another town with Etruscan roots and Etruscan tombs dot the hill below town. There’s also a museum in town with Etruscan artifacts. Most of Cortona’s monuments date from medieval times, including its 13th century town hall and clock tower in Piazza della Repubblica.

You can easily spend a day in Cortona but if you have extra time you can also visit nearby Arezzo, a pretty hill town that’s home to Piero della Francesca‘s magnificent fresco cycle, The Legend of the True Cross.

Wine Towns of Montepulciano and Montalcino

Montepulciano and Montalcino, south of Siena, are both wine towns as well as small hill towns.

montepulciano photo

Montepulciano (shown in the photo) is perched on a limestone ridge. Its two main streets run from the 13th century gate, Porta al Prato, up to Piazza Grande, the main square, and the fortress above. Medieval and Renaissance buildings line the streets and there are several places where you can taste the Vino Nobile wine produced in the area. Below town visit the beautiful Renaissance church, Madonna di San Biagio. In the area, you can also visit La Foce Garden.

Montalcino is another small wine town with a castle at one end. Visit the castle and go up on its walls for good views. There’s a wine shop where you can taste wine in the castle, too. Montalcino is in the Val d’Orcia, a beautiful valley of rolling hills dotted with vineyards. It’s a great place to spend a few days if you have more time.

Find out more about Tuscany or see more Tuscany hill towns to visit.

Recommended books about Tuscany:

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