Also known locally as "I Casaloni," Cepparello Castle represents a fascinating example of medieval architecture, set in a wild landscape. Erected in the 1100s, the fortification anciently dominated the surrounding valley and served as an important stronghold for the defense of the territory. With its imposing structure, characterized by walls and watchtowers, the castle reflects the military ingenuity of the time. The last bastion of Florentine power, it was destroyed by the Ghibelline faction Sienese after the notorious Battle of Montaperti in 1260.
Although it has lost much of its former glory, its ruins offer a glimpse of charm and history among the nature that thrives in the Monsanto countryside. The ruins can be reached by a path that leads into the woods from the road near Villa La Paneretta. It continues downhill and then climbs up the valley, for a total round-trip distance of about 3 kilometers and 800 meters of uphill elevation gain.
The castle's formerly strategic location also offers views of the surrounding area, making it an attractive destination for those who enjoy hiking among history and natural landscapes. Its presence continues to tell stories of the distant past and contributes to the rich cultural heritage of the area.