Rocca of Montestaffoli

About

The Rocca di Montestaffoli stands proudly atop the hill that dominates San Gimignano’s medieval skyline. Built in 1353 as a strategic fortress, its pentagonal layout and 280‑metre perimeter embraced the city’s defenders and could be accessed through a surviving tower that still offers breathtaking 360° panoramas of the Valdelsa valleys. Visitors are treated to sweeping views of the town’s iconic towers, the only remaining tower of the Rocca, and the surrounding countryside. An annual medieval tournament, "La Giostra dei Bastoni," takes place the third weekend of June, drawing enthusiasts of history and reenactment. Whether strolling the ramparts or admiring the architecture, the Rocca offers a unique glimpse into San Gimignano’s rich past and an unrivalled vista of Tuscany’s rolling hills.