San Donato in Poggio has an interesting history as the "last stop" on the Florentine frontier before the Republic of Siena's border. It was a popular place to exchange currency when traveling to or from Rome along the road that connected Florence to the Capital City.

The pretty stone village maintains its Medieval appeal with narrow streets lined with houses and interspersed with little piazzas. The walled town is still accessible by the historic city gates, the Porta Fiorentina and Porta Senese, each facing the cities that lie to the north and south of San Donato.

The main square, Piazza Malaspina is the hub of town. It has an octagonal well in the middle that used as a water source for centuries. The 15th century Gothic church of Santa Maria della Neve anchors the square, while the Renaissance era Palazzo Malaspina, once a noble residence and now a B&B, stands out, too. The bell tower, known as Torre Campanaria, was built in the 1200s.

The Pieve di San Donato is a Romanesque complex with bell tower that is a rare example of unaltered architecture from its historic roots, that date back to 989! There is a Della Robbia glazed terracotta baptismal font in the church.

San Donato in Poggio is set in the Chianti hills, a story-book type of landscape of farmhouses, vineyards, olive trees and rolling hills. There are cafes, a couple of restaurants and a few shops in town, and even a cooking school, the Accademia della Cucina Toscana. San Donato in Poggio is administratively part of the town of Tavarnelle Val di Pesa, and is near the famous Chianti wineries and towns (Radda in Chianti, Castellina in Chianti and Greve in Chianti) as well as being halfway between Siena and Florence.

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