Gaiole in Chianti is about 30 km northeast of Siena and 60 km south of Florence, connected to both by the SP408 (the Chiantigiana, or SR222) and secondary roads through the hills. By car from Siena it takes about 35 minutes; from Florence allow 1 hour to 1.5 hours depending on the route you take through the hills.
There is no train service to Gaiole. Buses from Siena run a few times daily and are run by TIEMME; the journey takes about 45 minutes. For most of the castle route and the surrounding wineries, a car is essential — they are scattered across a wide area and not reachable on foot from town. Cycling is a genuine option in spring and autumn; the strade bianche (unpaved white gravel roads) that connect the estates are famous among cyclists and give access to places unreachable by car.