Montespertoli is a lovely village in the middle of Chianti country. It's a typical Tuscan town on a hill with a patchwork of fields and staked grape vines below. Views of the countryside are what you see on picture postcards.
With Etruscan roots, it was taken over by the Romans thanks to its strategic position along the Via Francigena and Via Volterrana. An extensive trade network passed through here, connecting Florence, Volterra and Siena for the merchants and artisans. It came into its own during the Middle Ages, when its castle was constructed.
The Castello still stands in a prominent position. It was the possession of the Montegufoni, a powerful banking family, before ceding to the renowned Macchiavelli family. The town is home to a nice Museum of Sacred Art, showcased in the Church of San Piero in Mercato, with paintings, silver and tapestries on display. The panoramas are splendid. There are shops, restaurants and coffee bars scattered around the village, and a piazza for gathering and for festivals.
In fact, Montespertoli is known for its festivals! There is a Chianti Festival in May, and three different ones in November to enjoy - one dedicated to the area's white truffle, one for Vinsanto, a local sweet dessert wine, and one for the newly-made Vino Nuovo (which is traditionally served with roasted chestnuts).
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