Standing in ruins, the Rocca di Montestaffoli is a castle located at the western edge of San Gimignano. It was built in 1353 by the Florentines, who by then had taken control of San Gimignano. The castle was used to defend the town for the next two centuries, but when Siena took over from Florence, the castle was ordered destroyed. Today, only the walls and one of its towers remain intact, while the interior has been turned into a park planted with olive, fig and cypress trees. A climb up the tower of the Rocca is a must for outstanding views over San Gimignano and the surrounding Tuscan countryside. Just outside the castle is another small park with breathtaking views, as well as the museum of wine (Museo del vino).
The Rocca, a ruined fortress on the highest part of the hill, is surrounded by green parks and olive groves where you can sit and admire the Tuscan panorama, while munching on a cheese roll made up in one of the town's many shops. Alongside the Rocca is a charming little terrace where civilised foreigners sit sipping wine outside the Museo del Vino. This Museum of Wine is small, and of limited interest if you don't understand Italian, but the adjacent shop/bar, where you can discuss and buy bottles of local vintages, or enjoy wine by the glass, is an ideal stop on a sightseeing tour. The local wine is a white called Vernaccia di San Gimignano, and was a popular choice in Renaissance Florence.
Near the Collegiata there is a street which go the ROCCA DI MONTESTAFFOLI. It was built by Florence between 1353 and 1358. It was destoyed in 1558 by Cosimo I, but today you can see the origina shape and the towers. In the Rocca there is a Museum of the Wine.
From it you can see a nice landscape over the towers of the town.
This fortress dates from 1353 and offers a wonderful view over the northern part of the town and the surrounding countryside.
The museum of wine is on the left hand side of this photo. The museum offers visitors an itinerary through the wine culture, with multimedial demonstrations about the cultivation of vines and the wine production in the area. You can also taste some of the local wines.
In the north of town lies a ruined castle, Rocca di Montestaffoli. There is only one tower left of the castle. From here, you'll have a great view over the Elsa valley and the towers of San Gimignano.
The castle was built on the site of a Dominican monastery in the middle of the 14th century. With its 258 metres of walls it was an authentic fortress, defending the town to which it was linked by two drawbridges. At the end of the wars between Sienna and Florence it lost its strategic value and was dismantled in the 16th century.