Volpaia is a village in Tuscany, central Italy, administratively a frazione of the comune of Radda in Chianti, province of Siena.

Volpaia was built in the 11th century as a fortified village on the Florence-Siena border.

The historical account of vine cultivation in Volpaia dates back to 1172, marking the early origins of viticulture in this region.

In 1250, Volpaia played a significant role as one of the founding members of the Chianti League, a coalition formed by the Florentine Republic to manage its communities, divided into districts like Castellina, Radda, and Giaole, each with its designated territory.

These territories held strategic importance as frontline garrison towns during the Florentine-Sienese wars.