Just like many villages of Chianti, Gaiole in Chianti owes its origin to the importance it enjoyed in the past as a market place, thanks to its strategic position between Chianti and Valdarno. The urban structure of Gaiole, with the houses put in a row along the streets to favour the passage from houses to shops, as well as the funnel-shaped square built in a way to allow the coming of goods, prove the commercial origin of the village. Already in year 1000 the town market supplied the nearby castle, successively turned into a villa, Villa di Gaio, from where the town got its name.
The first document certifying the place-name is kept in the Abbey of Coltibuono, but it was in 1100 that the market reached such an important function as to threat the neighbouring market of the Barbiscio castle.
In 1215 Gaiole became so important, that it was annexed to one of the counties in which Chianti was divided. Sacked by the Aragonese in 1478, and after many years of occupation during the fight between Florence and Siena, Gaiole became the base of conspiracies of Siena refugees.
In order to keep the situation under control, the Podestà of Radda was forced to move here in 1492.
Some years later, during the conflict for the domain of the Peninsula by the two powers, both Pope Clemente 7th and Emperor Carlo 5th passed through this important junction point. After the fall of Siena, Gaiole followed its same destiny.
Today it appears as a modern town, with only few buildings testifying its glorious past.