Gaiole is set on a hill near the northern course of the river Arbia. There are several evidences of former etruscan and roman installations. The most important examples referred to the roman age are the ruins preserved at the Pieve di San Marcellino. In this town there are several churches as San Giusto in Salcio, San Polo in Rosso e Spaltenna, San Marcellino, San Vincenti and castles as Castello di Montegrossi, Castello di Lecchi and the famous Castello di Brolio. Gaiole, as many other town in this area, was the core of the conflict between Firenze and Siena. Today, as in the past, viticulture and olive growing are the most important activities.

The Chianti castles route is a tourist promotion project developed by the comune of Gaiole in Chianti, drawing its inspiration from the surprising number of castles, fortified farm houses, towers and fortified Abbeys in the area. The comune defined six itineraries that provide a very pleasant way to discover the architecture, history and present way of life of this part of the Chianti area.