Tuscany, with its rich history of Signorie (Lordships) and Principati (Principalities), but even before that as a network of rurally-based, self-governing production centers that over time grew into fortified villages, is perhaps the most famous region in Italy for the number and beauty of its medieval towns. There are truly countless ones. Some are well known and tourist-friendly, where the charm of the village and surrounding landscape blend beautifully with famous local traditions like wine and olive oil production, as well as renowned cheeses, cured meats, and exceptional gastronomy. Then there are others less visited by tourists, which keep a wild, timeless kind of charm.

We can only name a few here because the list would be endless… Actually, in Tuscany, almost every hilltop village was born in the Middle Ages -often built atop the remains of ancient Etruscan settlements, some of which still have visible relics – and many grew into fortified towns over time.

The ones we listed below are what we consider must-sees, arranged roughly by how close they are to Il Cubetto. But for those with a spirit of adventure, both virtual and real, our beautiful region is packed with countless other villages worth visiting. They might be less geared for tourism, but they are definitely authentic.