Monteroni d'Arbia owes much of its development to the expansion of Siena’s Santa Maria della Scala Hospital, which, as early as the 1200s, acquired vast lands in the area. In 1322, the construction of a majestic mill, managed by the Siena institution and located opposite the Church of San Donato, marked the beginning of the growth of Monteroni village, centered around La Grancia di Cuna. The route then winds through the heart of the Sienese clays, reaching Asciano, a medieval village with Etruscan origins. Breathtaking landscapes, rolling clay hills (biancane) and gullies (calanchi), and fairy-tale panoramas are the treasures that this fascinating variant of the permanent Eroica route offers. In September, the town comes alive with the traditional Palio dei Ciuchi, a celebration featuring a parade, flag performances, and rivalry between seven local districts.

Points of interest: Monteroni d'Arbia Mill, Ancient Walls, and Siena Gate.