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Hotel of the Week: This 900-Year-Old Borgo In Tuscany Also Hides a World-Renowned Private Golf Club

Restored by the Ferragamo family, Castiglion del Bosco, A Rosewood Hotel, opens for the season with decadent wine and culinary offerings, stargazing, and 18 holes surrounded by a UNESCO landscape

By Jill Sieracki
Aerial view of a villa with a pool surrounded by greenery and rolling hills under a clear blue sky.
Aerial view of Castiglion del Bosco, A Rosewood Hotel, in Tuscany. Photo: Courtesy of Rosewood Hotels

The breathtaking rolling hills of Tuscany are a tried-and-true destination for epicurean-focused travelers, who come to sample the robust wines, impeccable Italian cuisine, and even try their hands at some of the culinary adventures like truffle hunting. However, it’s not often that the Italian countryside tops the list for those more focused on birdies than Brunello.

Sunrise over a hillside villa with an infinity pool surrounded by lush greenery and distant rolling hills.
Aerial view of Castiglion del Bosco, A Rosewood Hotel, in Tuscany. Photo: Courtesy of Rosewood Hotels

Castiglion del Bosco, A Rosewood Hotel, a 5,000-acre estate dating back to the 1100s, offers the best of both worlds with an established vineyard producing Brunello di Montalcino, a two-Michelin-starred restaurant, and an immersive hands-on cooking school, as well as an 18-hole championship course designed by British Open winner Tom Weiskopf and clubhouse overlooking the UNESCO-protected Val d’Orcia.

Newly opened for the season, the property was meticulously restored by Massimo and Chiara Ferragamo. Medieval Tuscan farmhouses have been transformed into private accommodations, each individually customized while still adhering to traditional Tuscan aesthetics—warm woods, deep red tones offset by creamy neutrals, rough textures juxtaposed with sumptuous velvets and honed surfaces.

Elegant bedroom with a canopy bed, patterned cushions, wooden ceiling beams, and a view of greenery through a large window.
Villa Gauggiole at Castiglion del Bosco, A Rosewood Hotel. Photo: Courtesy of Rosewood Hotels
Cozy living room with pink sofas, round dining table, large windows, and a view of a garden.
Interior of a two-bedroom suite at Castiglion del Bosco, A Rosewood Hotel. Photo: Davide Lovatti
Open double doors revealing dining room with table, chairs, and a scenic view of lush hills through large windows in the background.
Villa Chiusa dining room. Photo: Courtesy of Rosewood Hotels

Gourmands visiting for the season can enjoy private tours through the 62-hectare vineyard, followed by tastings led by the hotel’s oenologist, Cecilia Leoneschi, or embark on a guided truffle-hunting session. Dinners can be savored in the two-Michelin-starred Ristorante Campo del Drago, where Executive Chef Matteo Temperini transforms ingredients culled from the estate’s organic kitchen garden into tantalizing dishes like Monnalisa gnocchi with wild mushrooms and vineyard garlic or Bassano white asparagus served risotto style with fresh almonds and nasturtium pesto. More casual meals are served in trattoria Osteria La Canonica, while hands-on cooking classes start in the garden before moving into the kitchen.

Outdoor restaurant setting with elegantly set tables overlooking scenic landscape and mountains in the distance during sunset.
Ristorante Campo Del Drago. Photo: Davide Lovati

More rest-focused guests can head to the spa, where products from the famed Florentine apothecary Officina Profumo Farmaceutica di Santa Maria Novella elevate skin and body treatments. Truly rejuvenating are some of the curated therapies that draw influence from Castiglion del Bosco itself, like a body scrub and massage inspired by the rose garden envisioned by Chiara Ferragamo, or the wine wrap and sauna evocative of the on-site vineyards.

Ancient stone ruins surrounded by tall cypress trees and lush greenery under a partly cloudy sky.
Castle ruins on the grounds of Castiglion del Bosco, A Rosewood Hotel. Photo: Davide Lovatti
Horse race in a crowded city square, with jockeys in colorful outfits, spectators watching from behind barriers.
Palio, the famous horse race of Siena. Photo: Courtesy of Castiglion del Bosco, A Rosewood Hotel

Those with an insatiable wanderlust will find plenty of room to roam at Castiglion del Bosco, where visitors can hike, bike, or travel by horseback past a 12th-century castle or chapel housing a 14th-century fresco by Pietro Lorenzetti without ever exceeding the property’s boundaries. Those planning their summer travel should look to experience the Festa Della Domenica, a celebration taking place every Sunday from June through September when the heart of the borgo turns into a lively fair with artisan booths and feast-style tables. Or come for the Palio di Siena Experience, a high-energy medieval horse race, during which Castiglion del Bosco guests can experience the longstanding tradition from a private palace overlooking Piazza del Campo.