Festa del Vino di Montespertoli
Montespertoli turns its town centre into a route of producer stands for nine days, with the main venues in Piazza del Popolo and Piazza Machiavelli. The 68th edition in 2026 had 21 wineries with stands plus two guest producers, tastings with the official festival glass at 5 euros, food stands run by 13 local associations, a Torneo delle Contrade and a historical parade on the final day. The festival grew from the town's traditional livestock fair, to which organisers proposed adding wine in 1957, with the first wine fair following in 1958. It was known for many years as Mostra del Chianti until a new organising committee restored the name Festa del Vino.