Montespertoli is a quiet Tuscan hill town about 30 kilometres southwest of Florence, sitting in the heart of the Chianti wine country. It is not a tourist destination in the usual sense — there are no blockbuster sights — but it is a fine base for exploring the rolling vineyard landscape between Florence and the Val d'Elsa.
The town itself is pleasant and unhurried, with a central piazza, a handful of restaurants serving honest Tuscan food, and views over the surrounding hills. The annual Chianti wine festival in June draws visitors from across the region. Two notable castles are nearby: the Sidney Sonnino Castle at the edge of town, ancestral home of an Italian Prime Minister, and Montegufoni Castle a few kilometres north, which sheltered Florence's greatest art treasures from the Uffizi during World War Two. If you are looking for rural Tuscany without the crowds of Greve or San Gimignano, this is a good bet.