5 medieval villages of Tuscany not to be missed


Fabulous views, ancient history: Tuscany has so much to offer and its cultural richness really leaves you spoiled for choice. So, to make things easier, we decided to tell you about 5 of the most beautiful medieval villages that are certainly worth a visit. Let's see them together!



Montepulciano is a village of medieval charm whose popularity is linked to the wine of the same name produced in its sun-kissed vineyards. It is located a few kilometers from Siena and is a village full of Renaissance palaces, ancient farmhouses, churches, beautiful squares and hills adorned with vineyards and olive groves. It’s located between Val di Chiana and Val d'Orcia, making it an excellent starting point to discover both.





UNESCO World Heritage, Pienza is a Renaissance town immersed in Val d'Orcia, rich in history and art. It is a few kilometers from Siena and offers many interesting attractions to visit including the central square, Palazzo Piccolomini and the beautiful Cathedral.

An architectural jewel, Pienza was completely restored between 1459 and 1462 at the behest of Pope Pius II and has the typical harmonious appearance of the fifteenth-century villages. Giovanni Pascoli called it the city "born from a thought of love and a dream of beauty".




Homeland of the famous Brunello wine, Montalcino is at short distance from Siena, Pienza and Monte Amiata. It is worth visiting the magnificent surrounding countryside, adorned with olive trees and vineyards that give the Val d'Orcia its peculiar aspect.

Do not miss the beautiful fourteenth-century church of Sant'Agostino, the neoclassical Cathedral, the Sanctuary of the Madonna del Soccorso and Sant'Egidio. In 2004 Montalcino was declared a UNESCO World Heritage.




Built in the tuff, Pitigliano is a charming village located in the heart of the Tuscan Maremma, considered one of the most beautiful in Italy.

In the fifteenth century, when the Jews were expelled from the state of the Church, many of them took refuge here forming a small but solid community, still rooted today. The peaceful cohabitation between Christians and Jews has earned the village the nickname of "Little Jerusalem". Do not miss the ghetto, the Synagogue and the kosher shops.



San Gimignano

Known for its medieval architecture and its many towers, San Gimignano is a UNESCO World Heritage town almost intact. The dense forest of towers, typical of the town, has earned it the nickname of "Manhattan of the Middle Ages". Today there are about 15 towers of which the highest is Torre del Podestà (54 meters), from which you can admire a truly incredible view.

Worth visiting is the Duomo, one of the most beautiful in Tuscany, and the Palazzo Comunale. Beyond the historical and artistic richness, if you happen to be in San Gimignano do not forget to taste a glass of Vernaccia di San Gimignano, the precious white wine typical of here.


Don't miss the beautiful places of Tuscany: discover our properties for rent and enjoy your stay in this amazing land!