Official documents dating back to 1215 show Gaiole’s importance as a trading post and this was to carry on expanding with the constitution of the “Lega del Chianti” in 1300 with Gaiole as the head of the “terzieri” together with Radda and Castellina.

The “Leghe” formed the basis for political and administrative division in the country areas under Florence and when necessary provided both money and soldiers. For four centuries the borough of Gaiole was considered the border between Florence and Siena and was consequently a target for raids and plundering until the definitive fall of Siena in 1555.

The system of the “Leghe” remained with both the Medici and the Lorena until 1776 when the “terzieri” of Chianti became the actual boroughs of to day.

See Nesto and Di Savino p6-7, 18, 46, 50, 97.