Rocca di Montestaffoli

The remains of the Florentine Rocca di Montestaffoli crown a hill above San Gimignano. Built in 1353, the fortress has a pentagonal plan with corner turrets and an entrance with traces of a portcullis and drawbridge.

Why it matters

The fortress was built after San Gimignano came under Florentine control. Today its walls form a public space whose elevated position looks across the town’s towers and the Val d’Elsa.

What to notice

The enclosure is pentagonal and measures about 280 metres around, with turrets at its corners. At the entrance, the antiporto retains features associated with a portcullis and drawbridge. A repaired turret provides a view across the historic centre and surrounding landscape.

Context and history

The Rocca dates to 1353, when the Florentines built a fortress on the hill. A local tradition, recorded by the town’s tourism portal, tells of an earlier castle associated with the Lombard king Astolfo and a later Dominican convent; the surviving remains are those of the medieval fortress. The site is also used for the town’s Ferie delle Messi festival.