San Casciano in Val di Pesa: Chianti, History and Trails

San Casciano in Val di Pesa lies on the hills between the valleys of the Pesa and Greve rivers. The location between the two river valleys provides the landscape setting for the historic sites, regional products and the Anello di Calcinaia loop trail.

History, Art and Notable Places

Porta al Prato is the only surviving gate of San Casciano’s medieval town walls and was rebuilt after the bombing in July 1944. The Church of Santa Maria al Prato was built in 1304. Next to Santa Maria al Prato is a painted cross attributed to Simone Martini and dated to the third decade of the 14th century. Since 2014, the Torre panoramica del Chianti has housed the contemporary installation “Bulk-Icosaedro” by Patrizio Travagli and WOKdesign.

Etruscan Traces and Sacred History

The Etruscan Tomba dell’Arciere is dated to approximately the middle of the 7th century BC. From San Casciano, it can be reached via the Via Grevigiana towards Mercatale; then follow the signs to Montefiridolfi and the Etruscan tomb. The Pieve di Santo Stefano a Campoli was first mentioned in 903. It lies on the slopes of Poggio di Monte Foscoli in densely wooded surroundings and offers a wide panorama in a rural setting.

Chianti and Olive Oil

San Casciano in Val di Pesa belongs to the Chianti Classico subzone and is known for the production of extra virgin olive oil. Chianti Classico and extra virgin olive oil represent two separate regional themes: the wine connection lies in the subzone, while the oil connection lies in local production. Those who include regional products in their travel planning can therefore consider these two themes separately.

Hiking the Anello di Calcinaia

The Anello di Calcinaia loop trail runs through the valleys along the Terzona River in the municipality of San Casciano in Val di Pesa. It can be hiked year-round. This year-round accessibility allows planning without being tied to a single season. The loop trail takes approximately four hours; this estimated time corresponds to a longer part of the day. For day planning, the approximate four-hour duration can be set aside as a separate time window for the entire loop trail. The start and finish are in the village of Calcinaia on the road from San Casciano in Val di Pesa to Mercatale, near the turnoff to Via Castelbonsi. As a loop trail, the route returns to the starting point in Calcinaia after it has been completed in full. The fixed starting and finishing point and the approximate duration give the hike a clear time frame without requiring any additional sections of trail.

Further Destinations for Orientation

Cerbaia, San Pancrazio, Ponte Rotto, Bargino, La Romola and Bagno A Ripoli offer further points of interest for planning your own trip.

For the main travel overview: Florence.