In 1202 and 1208 Fonterutoli was the location of two peace treaties between Florence and Siena, when the territory of Chianti was ceded to Florence.

A popular legend tells a funny story: At the beginning of the XIII century the two cities, worn by the war over Chianti, decided to assign the definition of the border to the meeting point between two knights each coming from their city at cockcrow.

The Florentines relied on a black rooster, which having been left without food crowed well before daybreak, allowing the knight from Florence to start with a great advantage and travel a long way before meeting precisely at Fonterutoli, almost within sight of Siena.

Florence brought its border to Fonterutoli on the line of Castellina, Radda, and Gaiole, and established the Military and Administrative Alliance of Chianti, choosing the Black Rooster as its shield.