San Donato is a small medieval village at the top of a hill minutes from the Firenze-Siena roadway about halfway between Florence and Siena. This is Chianti territory and the roads that take you to San Donato and then on to Greve or to Castellina in Chianti are some of the most beautiful in Chianti, with the rows and rows of vineyards as far as the eye can see mixed in with olive tree orchards, small woods, hamlets, farmhouses and wineries.
We recently visited the small town of San Donato and, while our visit was brief, it definitely left the impression that it would be the perfect location in Chianti in which to enjoy a calm and peaceful holiday. The town is small but it still conserves its medieval heritage. The heart of the town is still surrounded by the defensive walls built in the 12th century and along the western edge a watch tower still stands. We entered through the northwestern entrance called "Porta Fiorentina" (since it leads toward Florence), followed the main street, Via del Giglio, that has intersected the town since the 12th century. We passed a remaining tower-house from before arriving into the main square. Here, the imposing Palazzo Malaspina (part of it now the B&B Palazzo Malaspina) dominates one corner and right next to it is the Gothic church Santa Maria della Neve with its side facing the square. In the center, the octagonal well reflects how important a well was as the town's only water supply when the town was under siege. On the other side, is the Palazzo Pretorio which has not conserved its medieval look and is certainly less imposing than the facing Palazzo Malaspina.
We learned that for its small size, San Donato has played an important role in the centuries-long struggle between Florence and Siena. In 1218, the town came under the power of the city of Florence. Its importance then grew as it became a stop along the road from Florence down to Rome, and travelers coming into Florentine territory stopped here even to change their coins.
In 1176 and in 1265, two peace treaties between the republics of Florence and Siena were signed at San Donato in Poggio. Just 5 years before the second treaty, Florentine troops had organized just below the town as they were preparing to march to the Battle of Montaperti. The battle was a loss for the Florentine Guelphs and for this, the town and surrounding territory was ransacked after the battle. The peace treaty of 1265 did not last long.
Toward the end of the 14th century, the main pilgrimage and economic road started to pass through the nearby Tavarnelle and Barberino and thus the town's importance began to decline.
As we made our way out of the eastern wall called Porta Senese we come upon the main church of San Donato, the Pieve di San Donato. Built in Tuscan Romanesque style, documents date it back to the year 989. The baptismal font in terracotta and glazed by Giovanni della Robbia dates back to 1513.
These are the historical sights within the small medieval town of San Donato in Poggio. In our stop, before heading to a wine tour and tasting in the nearby Fattoria Montecchio, we saw two restaurants, a post office, pharmacy and several small shops that would make San Donato a perfect base for your holiday in Chianti!