Skip to content

4 medieval towns in Tuscany to visit in Val d’Orcia and Val di Chiana

4 medieval towns in Tuscany to visit in Val d’Orcia and Val di Chiana

Tuscany is a region famous throughout the world for its natural, artistic and cultural beauty. But it is also a land rich in history: medieval towns in Tuscany are the best way to take a real trip back in time to discover the past of this region.

In this article we made an overview of the villages to visit in Tuscany while now we focus on the most beautiful medieval towns in Val d’Orcia and Val di Chiana. We have chosen 4 of them that you can visit during a long weekend in this beautiful land.

Medieval towns in Tuscany: which villages to visit between Val d’Orcia and Val di Chiana

Among the Tuscan villages to visit in Val d’Orcia and Val di Chiana, we have chosen 4 that we think best represent the medieval charm of this land.


Just 20 minutes from Gargonza is one of the most characteristic medieval villages to visit in Tuscany, an example of medieval town planning that has arrived intact to this day.

Lucignano is a fortified village strategically located in the Val di Chiana valley. For this reason it has been contested over the centuries by the cities of Siena, Florence and Arezzo. The walls of medieval origin were initially built as early as 1371, then the village was further fortified around 1558 with the construction of a Fortress ordered by Cosimo I de’ Medici.

The urban layout is characteristic of medieval villages: there is a “rich” street facing south, wide and bright with more imposing residential buildings, and a “poor” street facing north, where smaller houses and social housing rise.


Montalcino is a medieval town in Tuscany famous for the production of the famous Brunello wine, one of the finest in Italy. Situated atop a hill, it dominates the Val d’Orcia with its majestic fortress.

The village is surrounded by ancient walls and still retains many historic buildings maintained as they once were. We recommend visiting the Montalcino fortress, built in the 14th century and now home to the Civic Museum, and the Cassero Tower, which will give you a wonderful view of the Val d’Orcia.

And since you are in the land of Brunello di Montalcino, stop and enjoy a glass of this wine while accompanying it with a local dish such as pici all’aglione or ribollita. If you happen to be in Montalcino in November, you can enjoy the Brunello Festival.


Montepulciano is one of the most famous and best preserved medieval towns in Tuscany. It lies perfectly halfway between the Val d’Orcia and the Val di Chiana: situated on top of a hill like most medieval towns in Tuscany, it offers panoramic views of the two valleys it dominates.

In addition to being famous for the production of the noble wine of Montepulciano, this small Tuscan village is home to numerous historic buildings. These include the Cathedral of Santa Maria Assunta, the Palazzo Comunale, and the Church of San Biagio, considered a masterpiece of the Italian Renaissance.

In addition to these stops of interest, it will also be pleasant just to take a walk through the medieval streets, admiring the historic buildings and enjoying the view of the Val d’Orcia countryside. Also, don’t forget a food and wine stop at one of the many bars, restaurants and wine shops you will find in the village.


Among the villages to visit in Tuscany, Radicofani cannot be missed.

Less well known than other medieval towns in Tuscany, it offers some truly striking and fascinating buildings. Among them, the Rocca is undoubtedly the main attraction: it is a large medieval fortress that towers over the hill and dominates the entire valley. You will see it from miles away, and today it is home to the Cassero Museum, where some archaeological finds discovered in the area are preserved.

Other monuments worth seeing are the Praetorian Palace, the Church of St. Agatha and the Church of St. Peter, which dates back to Romanesque times.

Of course, Radicofani also offers great satisfaction in terms of food and wine: we are in fact in the area of noble Tuscan red wines, Chianina and pici.

Visiting medieval towns in Tuscany starting from Gargonza

Castello di Gargonza is strategically located for visiting the medieval towns in Tuscany that we have recommended. n fact, it is located halfway between Arezzo and Siena, a short distance from Val d’Orcia, Val di Chiana and Chianti.

If you want to organize an excursion to discover the most beautiful medieval towns and you only have a few days to spare, Gargonza is the ideal starting base.

Discover all our accommodations: we have rooms and apartments to accommodate any number of people.

Buy now

Buy now

Buy now

Buy now