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Last updated: 19 January, 2023
Expert travel writer: Nicky Swallow

Originally a traditional country estate, complete with 10th-century castle and its medieval stone hamlet, Castello di Casole has been transformed into a luxury 5-star retreat.

Set in over 4,000 acres of wooded hillsides and farmland that includes a game reserve, 25 acres of organic of vineyards and 30 of olive groves, you could lose yourself for the day without ever leaving the property.

The castle, with its palatial spaces and 39 suites, has been meticulously restored leaving original features intact, while making concessions to 21st-century luxuries: a spa, superb infinity pool, gym and several restaurants.

This is an ideal choice for those looking for serious luxury and an away-from it all feel, although there’s easy access to Volterra, Chianti and its vineyards, the walled hilltop village of Monteriggioni and Siena itself.

Surrounding area

Set in 4,200 acres of unspoilt countryside, there is no danger of traffic noise. The only sounds will be of nature; birds, bees and the odd tractor. The views are of unspoilt, timeless Tuscan countryside.

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Key facilities

Airport transfers*
Beach: None
Fitness centre
Fitness classes
Golf course
Hot tub
Kids club
Parking: On-site (free)
Pool (adults only)
Pool (indoor)
Pool (outdoor)
Pool (kids)
Tennis courts
WiFi: Free

Food & drink

All inclusive
Kids menu
Restaurant on-site
Self catering
Additional charge

Room types


Room facilities

Air conditioning
Flat screen TV
Jacuzzi (private)
Pool (private)
Tea & coffee making facilities

Bedding options

2+ bedrooms
3+ beds
Connecting rooms
Rollaway/sofa bed

Bucket list experiences our writer says you must do in this destination, closest first

A day in San Gimignano

San Gimignano, Tuscany, Italy[16.5 miles]

Sometimes dubbed ‘Tuscany’s Manhattan’ for its clutch of slim medieval towers (visible for miles around), iconic San Gimignano is the region’s most famous (and most visited) hill town.

Best for ages: 18+ | Free

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A day in Siena

Siena, Tuscany, Italy[19.9 miles]

Arguably the most perfect medieval city in the world, Siena is a glorious ensemble of red brick buildings and exquisite monuments, famous for its fan-shaped Campo and Il Palio horse race.

Best for ages: 18+ | Free

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Palio di Siena

Siena, Tuscany, Italy[20 miles]

The most famous bareback horserace in the world, Il Palio is an extraordinary spectacle that sees horses and riders gallop three times round Siena’s glorious, medieval Piazza del Campo. A centuries-old means of settling of neighbourhood scores, it defines the social, cultural and political fabric of the city each year.

Best for ages: 13+ | Free | 3 hours

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A day in Volterra

Volterra, Tuscany, Italy[20 miles]

Steeped in history, the fortified hilltop town of Volterra offers glimpses of Etruscan and Roman life, among streets dating back to the 12th and 13th centuries.

Best for ages: 18+ | Free

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Other worthwhile experiences in this destination if you have the time or the interest, closest first

Dish of home-made creamy Tuscan chicken

Cooking classes at Jul’s Kitchen

Colle di Val D'Elsa, Tuscany, Italy[5.5 miles]

Colle Val d’Elsa Food writer/blogger and photographer Giulia Scarpaleggia and her husband run the excellent ‘Jul’s Kitchen’ offering a range of hands-on cooking classes alongside courses in food writing and photography. Classes are held in their house in the countryside between Siena and Florence.

Best for ages: 13+ | £70 | 3 hours

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Siena Market

Siena Market

Siena, Tuscany, Italy[19.7 miles]

Siena’s principal market, held each Wednesday morning, is one of the best in Tuscany. Stalls are set up at La Lizza, filling the streets around the Fortezza. Apart from excellent produce (cheeses, charcuterie, olive oil and wines, fruit and vegetables), you’ll find clothing, shoes, bags and household items.

Best for ages: 8+ | Free

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Pasticceria Nannini

Pasticceria Nannini

Siena, Tuscany, Italy[19.7 miles]

A historic cafe and pastry shop that’s been around for almost a century. It’s a great place to sample and buy panforte (the dense, flat cake made with nuts, dried fruit, spices and honey) and light, almond-y Ricciarelli biscuits.

Best for ages: 4+ | Free

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Osteria Le Logge

Osteria Le Logge

Siena, Tuscany, Italy[20.2 miles]

Located a minute’s walk from Piazza del Campo and occupying a former grocer’s shop with a retro vibe, Le Logge is a classic osteria. They offer a creative take on regional dishes such as tagliatelle with Tuscan ragu, stuffed rabbit with blueberries, black garlic and fermented carrot and braised beef cheek.

Best for ages: 13+ | £30

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Destination guides including or relevant to this place to stay


Tuscany, Italy

The astonishingly beautiful region of Tuscany has it all: art cities and ancient hill towns, high mountains and long sandy beaches, alongside luxurious hotels and some of Italy’s best food and wine.

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