Duration: Maximum 6 hours.

Through Cassia Road, it is possible to reach the beautiful Monastery of Monte Oilveto Maggiore, mother house of the Olivetan Benedictine order, founded by San Bernardo Tolomei in 1319. The coenobitic complex, surrounded by a dense forest of cypresses and timber trees, is still a cultural and spiritual center of considerable importance in the heart of the Crete area.
Immersed in the silence of the place, the visitor can admire real masterpieces of Renaissance art such as the inlaid wooden choir by Fra Giovanni da Verona (1503-1504) in the abbey church, and the main cloister frescoed by Sodoma and Luca Signorelli with stories of the life of St. Benedict.
Do not miss the monastic library and the art gallery. For lovers of good wine, the abbey opens its wine cellars to the public, testifying to the ancient rural work already promoted by Olivetan monks in the Middle Ages.

A few kilometers away, for those passionate about timeless destinations, a visit to the picturesque villages of the Asso valley is recommended. Surrounded by beautiful clay hills, these villages include Chiusure, a fortified medieval town; San Giovanni d’Asso, famous for the white truffle; Montisi, Castelmuzio,Petroio and Trequanda, urban settlements that grew out of ancient fortified farm or castles dating back to Middle Ages and which remain almost unchanged.
Continuing in the neighborhood, you can also reach Asciano, a medieval town that dominates the upper Ombrone Valley, which is still surrounded by ancient walls marked by square towers that characterize its urban profile. Through the main street, the visitor can admire medieval housing and important historical sites such as the Basilica of St. Agatha, a beautiful Romanesque church dating from the 11th century, and the Civic and Archaeological Museum.

Back on the Via Cassia, a stop in Buonconvento is also recommended. This medieval village was constructed at the confluence of the Arbia and Ombrone Rivers as an ancient place of rest and shelter for pilgrims, travelers, and merchants going along the Via Francigena. The town still has compact medieval city walls with very pretty urban views. In 1313, Emperor Henry VII (the Henry VII of Dante) died here. Along the main street of the village, one can see such notable monuments as the Ricci Palace, an interesting and rare Art Nouveau structure in the Siena area, which is now the seat of the museum of Sacred Art of Val d’Arbia, as well as the parish church of Saints Peter and Paul, which dates back to the 14th century but was renovated in 1705.