There are places that feel like a destination, and then there are places that feel like a world of their own. Tucked into the rolling hills of Tuscany’s UNESCO-protected Val d’Orcia lies one of Italy’s most enchanting escapes: Castiglion del Bosco, A Rosewood Hotel where time slows, wine flows, and every detail whispers quiet luxury.
Among its 42 suites and 11 private villas, Villa Agresto stands out as a deeply personal retreat, where rustic charm meets refined elegance, and where you don’t just stay in Tuscany… you live it.
A Legacy Rooted in Italian Heritage
Before becoming part of the Rosewood portfolio in 2015, the estate was owned by the Ferragamo family, whose vision preserved the soul of this historic land. Today, the property spans thousands of acres of vineyards, forests, and olive groves—just 119 km from Florence, yet a world away from the rush of everyday life.
The hotel season runs from mid-March through January, capturing everything from spring blossoms to golden autumn harvests and cozy winter escapes.
Villa Agresto
Think stone walls, wooden beams, sun-drenched terraces, and interiors that feel both luxurious and lived-in. Every corner tells a story of Tuscany, but with the quiet polish of five-star service.
And then there are the touches that elevate everything, and available in every one of the 11 Villas:
- A private heated pool overlooking the countryside
- Your own Land Rover Defender to explore the estate freely (as well as outside of the estate)
- A dedicated “mamma in the villa”, preparing meals and making you feel like part of an Italian family
- Daily breakfast delivered to the villa
- Complimentary Tuscan dispensa (welcome grocery upon arrival)
- Lunch or dinner each day (your choice) at one of the hotels’ restaurants or an in-villa dining experience prepared by one of the chefs (alcoholic beverages excluded)
A few details: 5,285 ft² (491 m²), 6 kings (or 3 kings & 4 twin) + cribs, up to 12 guests, and 6 fulls & 1 half bathrooms.
Dining: Where Food Becomes Memory
Food here isn’t just nourishment, it’s ritual, celebration, and connection.
A few highlights to discover for yourself
- Campo del Drago (2 Michelin stars): A refined culinary journey through Tuscan flavors, elevated with precision and creativity.
- La Festa della Domenica (every Sunday, from June to September): A Sunday gathering that feels like a big Italian family lunch: long tables, laughter, and unforgettable dishes.
- Dinner in the Vineyards: As the sun sets over the vines, candles flicker and courses unfold under the open sky.
Experiences That Define Tuscany
At Castiglion del Bosco, the experiences are as rich as the landscape itself.
- Truffle hunting (year-round) through forests with expert guides and dogs
- Hiking and biking across the rolling hills of Val d’Orcia
- Cooking school, where you learn the secrets of Tuscan cuisine
- Picnics in the vineyards, simple yet unforgettable
And for those who love the game, Rosewood offers something truly unique:
Italy’s only private 18-hole golf club, set against one of the most breathtaking backdrops in the country.
The Hotel at a Glance
Castiglion del Bosco, a Rosewood Hotel, is an elegant Tuscan retreat offering spacious suites and villas, exceptional dining, and a rich estate experience. Guests can enjoy two restaurants, a cooking school, organic gardens, a spa, sports facilities, a private golf club, a Brunello di Montalcino winery, and a dedicated kids club for younger travelers.
Bookings
Get in touch with us today to start planning your family’s perfect escape to Tuscany.
As part of the Rosewood Elite program (through 360 Private Travel), Sophibee can offer you exclusive benefits, including daily breakfast, a hotel credit, VIP status, and additional privileges to enhance your stay at any Rosewood hotel and resorts worldwide.
Ilonka Molijn – van Ginkel
Creator & Founder of Sophibee
Luxury Travel Advisor Sophibee & 360 Private Travel
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