At the slopes of the Amiata mont, between the Ombrone Valley and the final stretch of the Val d'Orcia, the town of Cinigiano grew around a XII century medieval castle, under the jurisdiction of some powerful vassals of the Aldobrandeschi counts. Later it was governed by the Guidi counts until the end of the Xiv century, when it was conquered by Siena. During the XV century, after the defeat of the Sienese army, Cinigiano entered the orbit of Florence.
Wonderful medieval village, traces if the ancient city walls are still visible, as well as military fortifications such as the medieval catle of Colle Massari, the Porrone castle (XIII century) and the Vicariello castle (XIII century). The Church of San Michele Arcangelo was re-built during the XVI century, when the façade was completed with pilasters and bricks. Inside it is possible to admire a beautiful XV century baptismal font and important XVII and XVIII century frescoes.