Etruscan in origin, as it is clearly established by recent archaeological finds, Radda in Chianti is located on a hilltop between the Pesa Valley and the Arbia one. The town's elongated medieval structure brings to mind the period, during which Radda was conquered by Florence, becoming the capital of the League of Chianti (1384), after being an important castle controlled by Siena, until 1176.
The Church of Santa Maria Novella, documented in a parchment since 1010, the Church of Santa Maria in Colle and the Church of Santa Maria in Prato are in Romanesque style. The Commenda of Sant'Eufronio in Volpaia presents many unusual aspects, due to its elements linked to the Florentine Renaissance architecture.