Radicofani lies at the foot of a basaltic cliff of volcanic origin crowned by an ancient fortress. A border pass between Tuscany and Latium, its importance is given, since the early Middle Ages, by its special strategic position on the Via Francigena, which constitutes its main road axis. On the place name of Radicofani there are various hypotheses, the most credited being that it derives from Radix Fanum (at the roots of the sacred place).

It was the inaccessible refuge of the famous Ghino di Tacco, whose exploits, were celebrated by Dante Alighieri and Boccaccio. The major village retains intact medieval features with the two churches of St. Peter the Apostle and St. Agatha that house works by Andrea della Robbia and his school. The Piazzetta del teatro is part of the ancient Jewish quarter. Behind the town, where the collapses of the ancient volcano are recognizable, lies the Isabella Woods.

The imposing building of the Posta, a hotel-customer’s hotel, dates back to the Medici era. Located on a hill in the village of Contignano, the walls, two gates and keep are still visible.