Gaiole in Chianti is castle country. The comune has mapped out a route connecting towers, fortified farmhouses, Romanesque churches, and medieval abbeys that rise from the vineyards at almost every bend in the road. The big draws are the Castello di Brolio — the largest and most visited — and the Badia a Coltibuono, but the smaller fortifications scattered across the surrounding hills reward those who explore on foot or by bicycle. Wine tasting, either at the estates themselves or at the small enoteca in town, is an integral part of any visit.