San Casciano in Val di Pesa
San Casciano in Val di Pesa is a hilltop village in the Florentine Chianti, between the Pesa and Greve valleys
Updated 19 July 2026
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The story
The story of San Casciano in Val di Pesa
Introduction and location
Perched on a ridge in the heart of the Florentine Chianti, San Casciano in Val di Pesa lies just a few kilometres south of Florence, within its Metropolitan City. The town overlooks the valley of the Pesa river, bordering the Val di Greve, along the ancient Via Cassia that once linked Florence and Siena. Surrounded by vineyards and olive groves, it retains much of its medieval layout, including sections of the old walls. Outlying hamlets such as Mercatale in Val di Pesa, Cerbaia, Montefiridolfi and Sant'Andrea in Percussina complete a largely rural municipal territory, offering a classic Tuscan hillside landscape.
History and origins
San Casciano's origins date back to the Middle Ages, when the town grew as a strategic control point along the Via Cassia, fought over by Florence and Siena. Over the centuries it was repeatedly fortified, and stretches of the old walls and gates can still be seen today. The area is also linked to Niccolò Machiavelli, who retired to the nearby hamlet of Sant'Andrea in Percussina after being excluded from Florentine political life, devoting himself to writing at his family estate known as L'Albergaccio. It was here that he composed part of his most famous work.
Nature and landscape
The countryside around San Casciano is quintessential Chianti: gentle hills covered in vine rows and olive groves, interspersed with woodland and cypress-lined ridge roads. The Pesa river valley runs through the municipality, offering views of cultivated fields and small rural hamlets. Scenic lanes connecting the outlying villages reveal a classic Tuscan agricultural patchwork of stone farmhouses, isolated parish churches and villas set among greenery. This largely unspoiled rural environment is one of the reasons the area appeals to travellers seeking slow, landscape-focused tourism.
Things to do and see
In San Casciano's historic centre, visitors can wander among lanes and squares enclosed by the old walls, visiting the Collegiata dei Santi Cassiano e Giovanni Battista, the town's main church, and the Museo di Arte Sacra, which houses works gathered from churches across the area. Just outside town, in Sant'Andrea in Percussina, the sites connected to Machiavelli can be explored. The surrounding hills offer walking and cycling routes through vineyards and wineries, many of which welcome visitors for tours and tastings. The hamlets of Mercatale, Cerbaia and Montefiridolfi are worth a stop to experience the slower pace of the Chianti countryside.
Flavours and traditions
San Casciano in Val di Pesa lies at the heart of the Chianti Classico DOCG production area, identified by the Black Rooster (Gallo Nero) mark, and the local economy has long been tied to winegrowing and extra virgin olive oil production. Many farms in the area offer cellar visits, guided tastings and direct sales of their produce. Local cuisine follows Tuscan tradition, with simple dishes based on bread, pulses, grilled meat and seasonal vegetables, often paired with wines grown on the surrounding hills. Local festivals and farmers' markets punctuate the calendar, showcasing the area's produce.
Not to be missed
- The historic centre of San Casciano with its medieval walls
- The Collegiata dei Santi Cassiano e Giovanni Battista
- The Museo di Arte Sacra
- L'Albergaccio in Sant'Andrea in Percussina, Niccolò Machiavelli's residence
- Chianti Classico wineries and tastings in the surrounding hills
To see
What to see in San Casciano in Val di Pesa
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Routes in San Casciano in Val di Pesa
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