Torrita di Siena suits couples and small families after a private pool in a walled Valdichiana town near Montepulciano. Sights in town come down to its walls, gates and churches, so bigger names mean driving.
Torrita di Siena is a walled town in the Valdichiana, a former stronghold of the Republic of Siena. High walls with square towers, rebuilt in 1528, surround the historic centre and are entered through four gates. The Romanesque church of Sante Flora and Lucilla holds a marble bezel attributed to Donatello. The homes are scattered across the countryside around the town. All have a garden and most a private pool, and they sleep around four to six. Montefollonico, a hamlet still inside its historic walls, is in the municipality.
A town a few kilometres away known for its medieval and Renaissance architecture and wine tastings in historic cellars.
A hamlet still surrounded by its historic walls, where the Vin Santo Path ends.
The city of Siena lies about 40 km from Torrita di Siena, while Florence is about 80 km.
Florence is about 80 km from Torrita di Siena, and Florence Airport has flights from London. Siena is about 40 km away. The homes are in countryside around the town, so you need a car.
The end of March brings the Palio dei Somari, a donkey race between eight town districts that is held every year. A Vin Santo event with markets of local products takes place in Montefollonico each December.
A donkey race held every year at the end of March. Each of eight town districts is given a donkey by lot, and the race runs four laps.
About 40 km from Siena and about 80 km from Florence. Montepulciano is only a few kilometres away, which makes it the easy day out.
Yes, mainly for Vin Santo: a walking route called the Vin Santo Path crosses the countryside and ends in Montefollonico. Montepulciano, known for its wine, is a few kilometres away.
For small families, yes. Homes here mostly sleep four to six, all have a garden and most a private pool. Larger groups will find little choice.
Written by the TrustedVillas team. Last reviewed October 2026.
Our villa experts are here to help you find the ideal property for your vacation. Contact us for personalized recommendations.