Casole d’Elsa, once a historic Etruscan settlement, is a village situated along the spine of a hill with a stunning panoramic view of the Sienese countryside. In the 11th and 12th centuries, the town was a fiefdom under the control of the Volterra Bishops, passing to Sienese control in 1260. Its strategic position meant it was perfectly situated to defend itself from external attacks, but also meant it subsequently needed to have new fortifications built, including two round towers that still stand, creatingthe village with its characteristic city walls.
The medieval village has also been given the Orange Flag of the Touring Club.