Tuscany Hill Towns Road Trip

Visit 6 Top Hill Towns

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 can be done in 4 days, although longer is better, especially if you want to linger or add on other towns.

Siena, Classic Tuscany Hill Town

Siena is Tuscany’s most well-known hill town and its largest with about 4 miles of walls surrounding its historic center. There’s a lot to see so plan to spend at least a full day in town. Since it’s centrally located and has plenty of restaurants and hotels, it makes a good base for visiting other Tuscan towns and 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 , 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.

If you have more time, spend an hour or two in the small, picturesque walled town of Monteriggioni.

siena main square
Piazza del Campo, Siena's Main Square

San Gimignano and Volterra

Northwest of Siena, these two towns can both be visited in the same day if you’re traveling by car but if you have more time consider spending the night.

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, on the main square, Piazza dei Priori.

  • Where to Stay in San Gimignano: Hotel Bel Soggiorno, on the main square.
  • Where to Stay in Volterra: Albergo Etruria, in a renovated 8th century building near Piazza dei Priori and the Roman theater.
View of Volterra, Tuscany Hill Town by James Martin

Wine Towns of Montepulciano and Montalcino

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

Montepulciano 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.

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. Then stroll through the picturesque town along the main street, lined with shops and places to eat or drink.

If you have more time visit La Foce Garden or more towns in the Val d’Orcia, a beautiful valley of rolling hills dotted with vineyards.

View of Montepulciano


Cortona, 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, the main square. Cortona’s Renaissance cathedral was built on the site of an Etruscan temple. Its facade dates from the 11th century. Inside are art works from the 16th and 17th century. Above town, the 16th century Medici fortress has great views.

  • Where to Stay in Cortona: Hotel Villa Marsili, a boutique hotel at the edge of the historic center, has a garden, views, and 14th century frescoes.

if you have more time visit Arezzo, a pretty hill town that’s home to Piero della Francesca‘s magnificent fresco cycle, The Legend of the True Cross or Anghiari, a small, evocative hill town.

Recommended books about Tuscany:

Tuscany, Italy: Small-town Itineraries for the Foodie Traveler
Rick Steves Florence and Tuscany
Books about Living in Tuscany and Umbria

Note: If you don’t have a car, these towns can be reached by bus or train, although train stations are outside town and require a connecting bus to reach the town center.

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Tuscany Hill Towns Road Trip originally appeared on MarthasItaly.com , updated: Aug 20, 2023.