Castiglion del Bosco – a 900-year-old borgo with two MICHELIN stars at the table

Above Montalcino, where the Brunello vines run out toward the Val d'Orcia, Castiglion del Bosco occupies a medieval borgo first recorded in the 1100s, bought in 2003 by Massimo and Chiara Ferragamo and turned, piece by piece, into one of Tuscany's most serious addresses. The MICHELIN Guide gives it Three MICHELIN Keys, its mark of an extraordinary stay, noting that the hotel is only the visible tip of a vast agricultural estate of preserved vineyards and forest. Within the same stone walls sits Ristorante Campo del Drago, awarded a second MICHELIN star in the 2025 guide under Tuscan-born chef Matteo Temperini, making it one of only two restaurants in Italy to reach two stars that year. A 12th-century castle still stands over the hamlet, a 14th-century Lorenzetti fresco survives in its chapel, and the estate has pressed Brunello since the early 1900s. The result is a working village reimagined as a hotel, not a hotel dressed as a village.

01The house

Castiglion del Bosco is a 5,000-acre estate in Montalcino, founded in the 1100s and restored by the Ferragamo family with deep respect for its history and soul, the hotel's own account explains. Massimo Ferragamo envisioned the property as a home rather than a destination, while his wife Chiara Ferragamo shaped its interiors piece by piece, travelling the country to source antiques and working with artisans to restore them.

The bones of the place are genuinely old: a 12th-century castle still crowns the estate, and its chapel guards a 14th-century fresco by Pietro Lorenzetti, a work the hotel itself calls a little-known treasure of Sienese art. Beyond the borgo, trails run through woodland, ruins and vineyard, and the estate has produced Brunello di Montalcino since the early 1900s, standing among the 25 founding members of the Consorzio del Vino Brunello. The hotel opened within the restored village in 2008.

02Rooms and suites

The resort's 42 suites fuse authentic Tuscan heritage with modern comforts: exposed wooden beams and antique furnishings sit alongside contemporary technology, with terraces, pergolas and views that stay green through the seasons. The MICHELIN Guide notes the suites range from 580 to nearly 2,000 square feet, and that many come with terraces larger than the room itself, pushing the stay out into the hillside.

Insider tip

In the UNESCO-listed Val d'Orcia, a short drive from Montalcino's 14th-century fortress and the Brunello wine routes.

Beyond the main borgo, eleven villas occupy restored 17th- and 18th-century farmhouses scattered across the estate, each with its own terrace, garden and heated infinity pool; villas also come with a Land Rover Defender or similar 4x4 for guests to explore the grounds during their stay.

03Where to eat

Ristorante Campo del Drago sits at the heart of the medieval village and has carried two MICHELIN stars since the 2025 guide, having won its first star in 2023. Executive chef Matteo Temperini, who joined the estate's kitchens in 2019, sources ingredients only from Tuscan soil, working with a trusted horticulturist on the resort's own organic vegetable garden and building the menu around its produce.

For something more informal, Osteria La Canonica occupies what was once the home of the village priest, serving trattoria-style Tuscan cooking, while a cooking school under the same name lets guests work alongside the kitchen team. In-villa dining extends the experience further, with garden barbecues, stone-oven pizzas and private breakfasts served in the villas themselves.

04The bar

The Lobby Bar occupies an intimate room with a Tuscan fireplace, built for a light lunch, afternoon tea or a late cocktail, while a separate Pool Bar serves the estate's two outdoor pools through the day. Guests also have access to three bars or lounges across the property, including the clubhouse at the golf course.

05Spa and grounds

The Spa draws on ingredients from a historic Florentine apothecary, set in rooms the hotel describes as suffused in earth tones, and opens daily from 10am to 7pm. Treatments include a Tuscan Botanical Renewal built around local olive oil and a Tuscan Herbal Ritual, alongside sauna, steam bath and treatment rooms for two.

Golf is the estate's other signature: The Club at Castiglion del Bosco is Italy's only private golf club, an 18-hole, par-72 course designed by Tom Weiskopf in partnership with Phil Smith and opened in 2012, laid across the contours of the Val d'Orcia hills. Weiskopf added a short 19th hole, the Brunello Hole, where players can settle a match over a magnum of the estate's own wine.

06The neighbourhood

The estate sits within the Val d'Orcia, a UNESCO World Heritage landscape of cypress-lined hills south of Siena, with the walled town of Montalcino and its 14th-century fortress a short drive away. The Castiglion del Bosco winery, one of the historic producers of Brunello di Montalcino, is on the grounds, with tastings and vineyard tours arranged through the hotel.

The hotel also builds its calendar around local ritual rather than imported spectacle: guests have joined the Festa della Domenica with villagers, and been taken into the Palio di Siena seated among locals and greeted by a Contrada captain, a way of watching Tuscany's oldest horse race from the inside rather than the stands.

For a weekend. For a lifetime.