San Casciano in Val di Pesa: Culture, Chianti and Landscape

San Casciano in Val di Pesa lies in the hills between the valleys of the Pesa and Greve rivers. The town combines this distinctive landscape setting with medieval and Etruscan history, contemporary art, and the regional character of Chianti Classico. This allows you to plan a stay combining culture, landscape and regional produce. One clear focus is either the historic sites or the Anello di Calcinaia circular route, which provides an entire day devoted to the landscape.

Cultural history across several periods

Porta al Prato is the only surviving gate of San Casciano’s medieval city walls. It was rebuilt after the bombardment in July 1944. The Church of Santa Maria al Prato was built in 1304. Next to it is a painted cross attributed to Simone Martini and dated to the third decade of the 14th century. Together, these two sites connect San Casciano’s medieval history with a specific artistic reference. A considerably older period is represented by the Tomba dell’Arciere. The Etruscan tomb is dated approximately to the middle of the 7th century BC. From San Casciano, the tomb 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 also expands the picture with a site of ecclesiastical history set in the landscape. It was first mentioned in 903 and lies on the flank of Poggio di Monte Foscoli in a densely wooded setting. From there, you can enjoy a broad panorama in a rural environment. Since 2014, the Torre panoramica del Chianti has also housed the contemporary installation “Bulk-Icosaedro” by Patrizio Travagli and WOKdesign. The range of places worth visiting therefore extends from the Etruscan tomb to contemporary art.

A circular route with fixed points of reference

The Anello di Calcinaia circular route runs through the valleys along the Terzona River in the municipality of San Casciano in Val di Pesa and can be walked year-round. The route takes approximately four hours. The starting point and destination are in the village of Calcinaia on the road from San Casciano in Val di Pesa to Mercatale, near the turn-off for Via Castelbonsi.

Chianti Classico area 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. Wine and olive-growing culture are therefore among the town’s defining regional characteristics. Together with the hills between the Pesa and Greve, this creates a profile in which cultural monuments are not presented in isolation but in connection with the landscape and the produce of the surrounding area.

Discover more places

If you would like to compare additional destination pages for your travel planning, you can find [Ponte Rotto](Ponte Rotto), [San Pancrazio](San Pancrazio), [Montefiridolfi](Montefiridolfi), [La Romola](La Romola), [Mercatale](Mercatale), [Bargino](Bargino) and [Cerbaia](Cerbaia).

For the higher-level travel overview: Florence.

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Monterappoli.