Situated at the foot of the pass that traverses the Chianti Mountains in the direction of the Arno Valley and located at the center of a densely populated zone, Gaiole has always played an important role in trade. It has existed since extremely ancient times.
Gaiole in Chianti’s communal territory amounts to 128.99 square kilometers (49.8 square miles) and it is located in a hilly zone that slopes down from the Chianti Mountains—800 meters (2,625 feet) at the highest point—to the westernmost banks of the river Arbia. The zone has about 2,300 inhabitants and 33.6% of the working population is engaged in agriculture (vines and olives are the predominant crops).
The first settlements date to an extremely ancient period, as indicated by the names of Etruscan or Latin origin of numerous sites and by the archaeological artifacts found in the Cacchiano area (a necropolis dating to the 2nd-3rd centuries) and at the San Marcellino parish church. The oldest settlements appear to have been concentrated around the parishes of San Giusto in Salcio, San Polo in Rosso and Spaltenna in the medieval diocese of Fiesole and San Vincenti in the diocese of Arezzo. All those structures still preserve their original plans as well as some extremely interesting traces of their Romanesque structures. Gaiole was once part of the feudal domain of the Firidolfis, who erected fortifications on the site and in the 11th century founded the abbey of San Lorenzo a Coltibuono, which was transferred later to the Vallombrosian monks. The numerous castles that dot the countryside were due to the influence exercised in the zone by the Firidolfis and, afterward, to the Republic of Florence’s need to establish defensive positions. Montegrossi, Vertine, San Sano, Lecchi, Cacchiano, Tornano, Castagnoli, Lucignano and Meleto are only some of the many castles of the period that, in most cases, have since been transformed into villas. The castle of Brolio, the seat of the Ricasoli family, is a special case. Its fortifications were constructed toward the end of the 15th century and it constitutes the first example of a defensive installation furnished with bastions. The complex was restructured in the 19th century by Baron Bettino Ricasoli, who converted it into a villa in a neo-Gothic style. The diffusion of so many castles in the zone surrounding Gaiole promoted its development as an important center of trade. It was also favored by its nearness to communities situated at the base of the valley through which passes the road leading from Chianti to the upper Arno Valley. As a fresco in the late 16th-century “Piante di Popoli e Strade” collection clearly shows, the town grew up around its main square laid out as an elongated triangle and lined with shops.