The history of Castellina in Chianti dates back to the time of the Etruscans: the Tumulo (mound) di Montecalvario and the Necropolis of Poggino are visible traces of an Etruscan community that settled in the Castellina in Chianti countryside from the fifth century B.C..
From the Middle Ages, the village between Siena and Florence has been at the centre of important historical events. Thanks to its strategic position, Castellina became Florence’s garrison, joined the Lega del Chianti (League of Chianti) and established itself as the capital of one of the Terzieri. At the centre of the struggle between the Republics of Siena and Florence, the village was fortified by hexagonal walls that are still standing today. With the birth of the Comunità di Castellina in Chianti came the end of the Lega del Chianti and today, it still has the fascinating atmosphere of its glorious past.
The legend of the Gallo Nero is linked to Castellina in Chianti: to end the strife in the Chianti region, the Republics of Siena and Florence decided on a race between riders starting at cockcrow. The Sienese overfed a white rooster to make him sing louder, while the Florentines chose a black rooster that was deprived of food. The black rooster, hungry and exhausted, anticipated the sunrise with the stronger crowing, marking the start of the Florentine’s ride to the area of Fonterutoli in Castellina in Chianti.