San Casciano in Val di Pesa is often referred to as the gateway to Chianti, because it’s the northern most town in the region, but the moniker holds when you look out over the vineyards that roll away to the south of the town. Our Gurus’ picks for the best places to stay in San Casciano in val di Pesa include a couple of Tuscan castles, some beautifully converted mid-sized villas, and farmhouses that have been converted into rural idylls. Our list also includes some properties with incredible views of Chianti, and incredible wine lists too!

The Chianti region undulates a bit more than the rest of Tuscany, and if you’re driving an increase in hairpin turns will herald your arrival into the area. San Casciano perches at the top of a hill; it’s an impressively medieval sight on the horizon, though the surrounding area is also scattered with hill forts, hamlets and churches. The centre of the town is charming with its historical heart ringed by 14th century walls, though this is very much a working Tuscan town. Because of this, it is slightly off the tourist track which means that you're likely to find authentic trattorias where you can sample the real flavours of the region.

As with many of our recommendations in Tuscan towns, not all of the best places to stay in San Casciano in val di Pesa are within the walls of San Casciano. Some are converted villas or farmhouses in the valley below, or on hillsides around the town.

The Best Places to Stay in San Casciano in val di Pesa

For Romantics

• The Villa Mangiacane is a five star villa hotel with a traditional, rosy exterior, and 27 romantically decorated rooms and suites, complete with antiques, four-poster beds, open fireplaces and huge bath tubs. Some of the larger suites have double height ceilings with mezzanine levels. And there’s a butler service. When dining you’ve the option of private meals in your room, or on a romantic terrace, or in the elegant restaurant — which also has a notable wine list. Everywhere you look the views are really something too.

For Families

• The Villa Il Poggiale is a sun-kissed, 16th century Tuscan villa with towers, pillars, fragrant gardens, and an incredible view. There are just 24 rooms and suites, all individually, and charmingly, decorated with paintings, frescoes and antiques. The restaurant specialises in regional cuisine, and of course serves an impressive list of regional wines. There’s also a pool, gym, spa, complimentary bike hire, and babysitting available.
• The Castello di Bibbione is a traditional Tuscan castle with glorious views over the Chianti countryside from many of its 13 farmhouse-style apartments, but especially from its sunny terraces and gardens. This is a good choice for families and groups, with some apartments sleeping up to six; there’s also a private villa on the property, which sleeps up to 12 and has its own private pool. The communal pool is lovely, an impressively proportioned infinity pool, and there’s a wellness centre. The Castello also has guest bikes. Self-catering, though they do offer breakfast.

For a Rural Retreat

• The Villa I Barronci is a carefully converted villa in beautiful grounds on the outskirts of San Casciano, in the direction of Florence. Its 21 rooms and suites have been simply arranged and decorated with lost of white against wooden floors and beamed ceilings. Our Gurus' favourite rooms have mezzanine levels, creating even more space. The pool has a view, and there’s a small wellness centre. 
• Salvadonica is a carefully converted farmhouse set amongst vineyards and olive groves. The original stone and tiled floors, stone walls, and wood-beamed roof have been really beautifully incorporated into the contemporary style of the current building, and the 19 rooms are light, airy, and stylishly minimal. The best rooms have frescoes and vaulted ceilings. As well as a pool surrounded by olive trees, Salvadonica has a tennis court and boules green. The restaurant serves excellent Tuscan cuisine, on a beautiful terrace.

For an apartment or villa

• If you think a self-catering option would best suit your needs then browse through the wide variety available online with our partner, Booking.com.

Travel Information

• Florence Airport, Amerigo Vespucci, is about half an hour away from San Casciano in val di Pesa by car. Pisa Airport may be useful to visitors too, about an hour's drive away.
• If you plan to hire a car, which we would advise if you want to get out and explore further afield, we recommend you visit our online partner Rentalcars.
• Like most of Tuscany, San Casciano in val di Pesa is busiest during the summer, but also hottest. If you’re not a fan of temperatures over 30°C, then planning your trip for spring or autumn will probably be more pleasant for you. April through June, or September through November are more pleasant weather wise. Easter and the Sancascianese Medieval Carnival are big events to look out for, and December offers all the festivities of Christmas.

Still not sure where to stay?

• You could expand your search to include all the best places to stay in Tuscany
• Consider some of Tuscany’s other historic towns. What about Cortona, Siena, Montepulciano, Arezzo or San Gimignano?
• Consider refining your search by the kind of accommodation you’re looking for? See our recommendations for the best wine hotels in Chianti, for example.
• Alternatively, you could contact one of our friendly gurus for personalised advice.