Gaiole in Chianti is a sleepy Tuscan village today, but in the Middle Ages, it was a strategically important center ringed by the strongholds of Brolio, Vertine, Barbischio, and the turreted Castle of Meleto (Castello di Meleto). The castle and estate have long been associated with winemaking, and today the landmark is one of the top attractions on wine and castle tours of Chianti. Join a guided visit of its frescoed rooms, 18th-century theater, and historic wine cellars, as well as a vineyards tour and tasting sessions of award-winning Chianti Classico and other local wines in the castle’s enoteca.