Top 5 Towns in Tuscany

Understandably, Tuscany holds a special place in the hearts of most who visit it. One of the great pleasures of a Tuscan holiday is exploring different towns and finding the one you like most. Of course, the best way to do so is become more intimate with a place by settling down for a while in a villa. Here are our top five recommendations for places to love in one of Italy’s most romantic regions.

Top 5 Towns in Tuscany 11. Lucca
Surrounded by city walls thick enough that locals jog and even cycle on top of them for their daily exercise, Lucca is a large and important historical center. It has grown to over 90,000 inhabitants, but still feels much smaller and more traditional than Florence. People come here to appreciate Lucca’s many beautiful churches, the Torre Guinigi that has ancient oak trees on top, and excellent coffee bars.

2. San Gimignano
The City of Beautiful Towers earned its nickname with 14 spectacular torres that form a unique, pastoral skyline visible from the surrounding countryside. No cars are allowed within the city walls, which encompass almost all of the town’s 7,000 residents. The result is, as you might guess, a perfectly peaceful and romantic medieval-feeling atmosphere of winding cobblestone streets full of traditional restaurants, farmer’s markets, and bakeries. It’s definitely not to be missed.

Top 5 Towns in Tuscany 23. Siena
Perhaps most famous for the annual Palio di Siena horse race, this medium-sized Tuscan city has a lot to offer. Its huge, fan-shaped central piazza, where the race takes place, is an excellent place for people watching, and conveniently enough the people of Siena are some of the best to watch. Its status foremost as a university town gives it a distinctive and quirky flavor that has resulted in the proliferation of unique bars, cafes, and galleries. Of course, there’s no lack of history here either, with more than enough cathedrals, towers, and more.

4. Cortona
Did you read or watch Under the Tuscan Sun? Then you already know a bit about Cortona. Many expats now call this hill town home, and with good reason—it’s one of the best places where you can still enjoy the slow pace of Italian life. With its great views, nature walks, cafes, and more, this is a perfect place to settle down for a while. Many find that once they come, they can’t leave. The city retains much of its ancient history, and is surrounded by Etruscan walls more than 3000 years old.

Top 5 Towns in Tuscany 35. Florence
You can’t visit Tuscany without at least stopping in Florence. While it may be a bit overrun with tourists coming to see Michelangelo’s David at the Accademia Galleria (which is worth the visit, trust us), Florence remains one of the prettiest Renaissance cities in the area. Check out the Baptistery, the Duomo, Medici Palaces, central piazza, and endless museums to get a sense for the historical nature of the city. This was (and still is) one of Europe’s great centers for arts and architecture.

Inspired to learn more? You can find out more about Tuscany and start planning your dream holiday now.