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 Castel Monastero 

Monastery made modern

Set in a restored medieval monastery deep in the Tuscan hills, Castel Monastero feels more like a tiny stone village than a conventional hotel.

The glorious setting does most of the talking here. A cluster of honey-coloured buildings gathered around a quiet piazza, with vineyards, woodland and big open skies stretching in every direction. Castel Monastero started life nearly a thousand years ago, and the sense of history still hangs around the place, but it has been carefully turned into a beautifully restored retreat rather than anything remotely museum-like. Days settle into an easy rhythm of long lunches, a swim, perhaps a wander through the grounds before dinner. If you like the idea of countryside calm and a hotel that encourages you to slow down, it works beautifully.

Why we love Castel Monastero

  • You stay in an authentic medieval hamlet rather than a purpose-built resort, but still get all the luxury hotel comforts.

  • There’s an excellent fine-dining restaurant on site, ideal for celebratory evenings or when you feel like making dinner an event.

  • There’s a proper destination spa with indoor pools, hammam, sauna and a full thermal circuit.

  • You get a choice of doing very little or filling your days with wine, food and Italian countryside experiences.

5 stars
Apr - Oct
Rural Tuscany
Pisa: 2¼ hours
In the Chianti countryside near Siena, surrounded by vineyards, olive groves, and rolling farmland.
Allow about 1 hour 15 minutes by car from Florence Airport, or around 2 hours from Pisa.
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Facilities

  • Restaurants & bars
  • Board
  • Spas & wellness
  • Activities
  • Families
  • Good to Know

Food is taken seriously here. Contrada sits on the main piazza and offers a refined dinner experience when you feel like making an evening of it. La Cantina is the relaxed alternative, tucked into what used to be the monastery’s wine cellars and serving straightforward Tuscan cooking for lunch and dinner. It’s the kind of place where you happily linger over pasta, grilled meat, and a bottle of local wine.

Contrada
A refined Michelin-starred restaurant (1 star Michelin) dinner option on the piazza. Here, seasonal Tuscan ingredients are turned into thoughtful, beautifully presented dishes.

La Cantina
A relaxed cellar restaurant serving classic Tuscan cooking.

Chigi Bar
The natural gathering spot for an early evening aperitivo or a slow nightcap once the countryside settles into quiet.

Aqva Pool Bar
The place for a spritz, something light to eat, and a long pause between dips in the pool.

What's Included

Breakfast at Contrada

Upgrade Options

Half Board • Breakfast at Contrada • Lunch or dinner at La Cantina

The spa is a major part of the appeal rather than a small add-on. Spa Monasterii spreads across around 1,000 square metres with two indoor pools, including a high-salt relaxation pool, plus sauna, hammam, whirlpool, a Kneipp path (where you walk through alternating warm and cold water pools to boost circulation), and treatment rooms. Outside, you’ll find three swimming pools set among the gardens with views across the surrounding countryside. There’s also a gym and occasional yoga sessions.

The hotel offers wine tastings, cooking classes, and truffle hunting, which suit the setting perfectly. Tennis courts are on site, and the surrounding countryside is great for walking or cycling. If you feel like dialling things up, staff can also arrange Vespa trips through Chianti and hot air balloon flights.

Families are welcome here, particularly those happy with a slower countryside pace. Connecting rooms and larger suites make it easier to spread out, and restaurants are relaxed enough to accommodate younger diners. During the summer months the hotel runs a weekly programme of activities for children aged three and over, including games, treasure hunts and crafts. Babysitting can also be arranged. The indoor spa facilities are adults-only, and the rural setting means most of your time will be spent enjoying the hotel and its grounds rather than popping out to nearby attractions.

A tourist tax is payable locally at the hotel.

Transfers are not included.

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