The Tuscan village of Roccastrada rises on top of a massive layer of trachyte, a volcanic rock. At 475 meters above sea level, it offers a very impressive view of the coastal plain. At present there is no evidence to suggest that the development of the settlement occurred in a period prior to the Middle Ages. Roccastrada, in fact, is first mentioned in 1140.

Of particular interest are the Church of St. Nicholas and the Museum of Vine and Wine. The former, located on Via IV Novembre, was most likely built in a time frame prior to 1283. Its interior houses two frescoes depicting the annunciation and the Madonna and Child. The second is located in the small square of the Clock Tower. The premises housing the museum were carved entirely out of the rock on which the buildings of the entire historic center rest on their foundations. One of the goals of the museum facility is to raise awareness of the local peasant culture, working tools and especially the wines of the Roccastrada area.
Not only that, during the summer period the town hosts various types of festivals and celebrations related to ancient folk traditions. The "Palio dei Ciuchi" is undoubtedly one of the most anticipated events for residents and tourists. Jockeys riding their donkeys ride a course through the main streets of the village. The race is preceded by the parade of the Palio, followed by decorated and colorful floats, which brings its greetings to the eight participating contrade.
Roccastrada, is just one of the many medieval villages that populate the municipal territory. Among those most relevant, both historically and scenically, are Montemassi, Roccatederighi and Sassofortino. The second location mentioned for example is particularly well known in Maremma for its historical re-enactment, called "Medioevo nel Borgo," which the Pro Loco of Roccatederighi promotes every summer. From Sassofortino, on the other hand, it is possible to reach the very close castle of Sassoforte, built in all probability around the year 1000, as we find it mentioned in an 11th-century document, which has undergone a multi-year project of archaeological excavations conducted by theUniversity of Siena.