Rocca di Montestaffoli (Rock of Montestaffoli), San Gimignano

The Rock of Monestaffoli is a 14th century hilltop fortress a short climb from the Cathedral Square (Piazza del Duomo). Built in 1353 by the Florentine administration of San Gimignano, the Rock provided an excellent strategic view of the Elsa Valley and environs. In 1555 duke Cosimo di Medici demolished the fort. Today, only the shell remains.

But, what a shell! An idyllic architectural ruin surrounded by olive trees and overlooking the medieval town and the valleys below. For years it has been the venue for summer performances and concerts. It has also become a showplace for contemporary art. The view is best from a corner tower accessed by a staircase open to visitors.

The Rock of Monestaffoli has small gardens, wandering paths among the olive trees and a medieval well in the center of the park. It is a classical country ruin, romantic and very photogenic. It is perfect for a picnic. Entrance through the park is free.