Hill Towns and Walled Cities

Step back in time and visit the tiny hill towns and walled cities of Lucca, Siena, Cortona, San Gimignano, Volterra, and Montepulciano as you explore Tuscany.

•    Lucca: The ancient walled city of Lucca was founded by the Etruscans and it became a Roman colony in 180 BC and the birthplace of Giacomo Puccini, the great operatic composer. The walls are well preserved, and visitors can walk completely around the historic city center on the bicycle paths atop the walls. The towers provide panoramic views, and the grid design in the center of town follows the original Roman street layout. Piazza San Michele now stands on the site of the forum, and the Piazza dell’Anfiteatro displays ruins of the ancient amphitheater. San Martino Cathedral is the centerpiece of town. Lucca has a multitude of restaurants for your enjoyment.

•    Siena: Like other hill towns in Tuscany, Siena was settled by the Etruscans. The town is best known for its exuberant horse race called the Palio di Sena that takes place twice a year in the summer. Visitors come to marvel at the spectacle of bareback riders in medieval costumes representing their districts gallop around the Piazza del Campo on wild horses. Other attractions include the Romanesque/Gothic cathedral, the Palazzo Pubblico, Bibliotecca Piccolomini, Mangia Tower and Fonte Gaia.

•    Cortona: The hill town of Cortona is famous as the location in Francis Mayes best seller, Under the Tuscan Sun. 3,000 year old Etruscan walls still encircle the city, and the ancient Etruscan presence is seen in architectural elements around town. Cortona is known for medieval buildings, gorgeous views, a commune and a sizable ex-pat community.

•    San Gimignano: This small walled hill town has well preserved medieval architecture, making it a UNESCO World Heritage Site. 14 of the 72 original belltowers remain, adding to the charm and historical interest of the city. Ascend the 177-foot Torre Grossa tower for gorgeous views. Browse among the shops and purchase local products such as saffron and white wine, Vernaccia di San Gimignano. Walk the town and visit the Collegiata di Santa Maria Assunta, the Duomo, Palazzo Comunale for art and world famous gelato in the Piazza della Cisterna. There are also a couple of torture museums with over a hundred gory exhibits.

•    Volterra: Located near San Gimignano but hosting far fewer tourists, this walled town features medieval structures and Etruscan sites. There is also a Roman theater, baths dating from the 4th century and ruins of a Roman forum. See the Piazza dei Priori, the main square, the duomo and baptistery, and the medieval wall and six gates that surround the historic center. Medicea Fortress is perched high up on the hill. The town hosts a Medieval Festival on the 3rd and 4th Sundays in August each year, with pageants and entertainment.

•    Montepulciano: Montepulciano is best known for its Vino Nobile and other wines produced from the Montepulciano grape. This Renaissance hill town features the Palazzo Comunale, cathedrals and churches, and walls that date back to the 14th century.


"Isle Blue is everything they say they are. They were a pleasure to deal with and were very responsive and informative. The pictures on their website are exactly what you end up getting and they provide full concierge service throughout your stay. My family and I had an amazing time and before we even returned home, we went to the Isle Blue website to check out their inventory for our next vacation. They really are just that good!"
Marc W.
Stay up to date with our special offers, travel tips and the latest Isle Blue news.