Anyone longing to see a truly authentic Chianti town should head straight for San Casciano Val di Pesa. Pretty, historic, full of local colour, typical trattorie and bars that spill out onto the street, this small town is now fast becoming a crucial stop on the Chianti trail.

San Casciano is perfect as a day trip destination from Florence or even as a base from which to explore the area, as it’s one of the gateways to the Chianti region. Located 18 kilometres south of Florence, it’s easy to get to by car or public transport, and offers a nice range of restaurants, gelaterie and boutique shops to keep you entertained.

Visit San Casciano Val di Pesa in Tuscany, Italy

It’s one of the most sought after destinations for people who want an alternative to Florence but who are looking for a place with a bit of life. Lots of expats have decided to buy houses in or around San Casciano because of its superb location. What’s more, it’s not a sleepy country village, but a lively place with some very good restaurants, (we absolutely love the “Cantinetta del nonno”!), a theatre, a cinema, and a few nice places for aperitivi.

There’s a lovely green space just outside the walls, “Il Piazzone” with a great view over the valley and plenty of space to relax, where people of all ages can meet for a chat or an ice cream. In San Casciano Val di Pesa you can savour real Tuscan life in a place that hasn’t been overtaken by tourists yet. Better still, it’s a very good place to choose if you’re travelling with kids.

⇒ Find out about the best places to visit in the Chianti region.

Charming small towns in Tuscany to explore during your stay.

San Casciano Val di Pesa

Museum of Sacred Art Giuliano Ghelli

There’s a small but well kept Museum of Sacred Art (entrance from the library in via Lucardesi, 6). It hosts religious-themed paintings from the 14th and 15th centuries, including Cenni di Francesco famous for his late Gothic taste, the Sienese Ambrogio Lorenzetti, and a painting attributed to 13th century master Coppo di Marcovaldo. Here Saint Michael defeats Lucifer and saves a bull from certain doom.

The museum hosts a rare piece from the Master of Cabestany, an anonymous sculptor active in the second half of the 12th century. It’s a sculpted column representing the birth and the Baptism of Christ, with plenty of details. His figures are peculiar: they have long faces, almond-shaped eyes and many are folded in drapery.

⇒ Art passionate? Don’t miss our post about the Best Museums in Florence.

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A long history, and some illustrious guests in San Casciano Val di Pesa

Built along the ancient Via Cassia that linked Florence to Rome, San Casciano was an important stronghold of the Florentine Republic against rival Siena. After being attacked too many times, Florence decided to fortify the village with a set of walls.

The Emperor Henry VII passed through here in 1312, and later members of the Medici family stayed in San Casciano Val di Pesa. Once Siena had been defeated, the town was reinvented as a favourite stop for royalty, and the rich and  powerful, on their way to Rome. They used to stay at the ‘Cassero’, today converted into private flats.

Not much remains of the town’s Medieval walls. But if you head for the the piazza, you’ll see a silvery stag standing atop the wall. This is a contemporary artwork by Mario Merz that represents the freedom of nature. There is also a neon Fibonacci number sequence, that symbolises our efforts to control nature.

⇒ More trip ideas? Here’s a few itineraries in Tuscany made for your interests!

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When to go and how to get there

San Casciano Val di Pesa is a good place to base yourself if you’re visiting Florence or Siena. With regular and frequent bus services between San Casciano and these towns (but also Greve in Chianti, and other destinations in the Chianti area) you could organise your sightseeing during the day and come back here before dinner. Especially in Summer it’s a lively and pleasant place to be, with plenty of events to enjoy.

Tip: every Monday morning San Casciano Val di Pesa puts on a lively market that sells everything from cheap clothes to shoes and flowers, fruit and vegetable. While on Wednesday afternoon all shops are closed. The big supermarket “Coop” is just outside the centre, and it’s open all day. Shops are open between 9-13 and 4:30-7:30pm (closed on Sunday).

Note: avoid peak hours (8-9am and 6-8pm) when travelling to and from Florence, as this is quite a busy road.

What to see nearby

Villa Machiavelli, Albergaccio – the author of “The Prince” passed his exile at his estate in Sant’Andrea in Percussina (a few kilometres from San Casciano). Today it hosts a charming restaurant, and they organise tours of the Villa and wine tasting too.

Cantina Antinori – at Bargino, a few kms. from San Casciano, you can visit the splendid Antinori cellars. A wine tasting experience in an architectural masterpiece, one of the Top Experiences for Wine Lovers in Tuscany!

=> One Day Itinerary Exploring the historic towns of San Casciano, Montespertoli and Certaldo.