Among the rolling hills of Val d’Orcia and the chestnut forests of Monte Amiata lies the municipality of Castiglion d’Orcia, which, in addition to its renowned village, includes a number of small hamlets. This land, rich in historical, cultural, and artistic beauty, offers a route filled with unique landscapes that will captivate cyclists as they gaze at the distinct silhouette of the Aldobrandeschi Fortress, dating back to the 10th century, perched atop a rocky spur 570 meters high. The village is considered the oldest settlement in the area, and as of August 2023, following extensive restoration and safety works, the Aldobrandeschi Fortress has reopened to the public for visits.

Points of interest: Aldobrandeschi Fortress, Tentennano Fortress.