Since the sixth century before Christ, during the Etruscan period in the territory of Montemassi was never stopped the cultivation of the vine.
The grounds of the estate are dominated by a fortified settlement dating back probably to the tenth century. It is with the family of Aldobrandeschi that the castle comes alive in medieval history, until their expulsion in 1260, when the Sienese troops destroyed the castle. Pannochieschi will be to rebuild it, equipping it with a new fortification, until the fateful year, 1328, which was the attempted rebellion in Siena, with the help of Castruccio Castracani.
But the Sienese militia had won. The event was immortalized in the famous painting by Simone Martini, which is in the public palace of Siena, depicting Guidoriccio da Fogliano on horseback in the background, in addition to Montemassi castle, painted the tents of the camp surrounded by some of his troops vineyards. The property south of Montemassi was assigned to the family of Siena Bichi.
In 1632 the Grand Duke Ferdinand II of Tuscany founded the Marquis of Montemassi and Roccatederighi, led by Secretary of the Malaspina Mulazzo guide which is then passed to the Cambiaso in Genoa, the Marquis and the Marquis of Roccalbegna Bichi Bichi Rispoli until 1826. For plots dynastic property of Montemassi passed to Forteguerri, other noble Sienese family who strongly innovated over the centuries agriculture Maremma and embellished art their possessions from great patrons. Since 1998 the estate Rocca di Montemassi is owned by the Zonin family.
Images Rocca di Montemassi