This Gorgeous Tuscan Resort Was Once The Ferragamo Family’s Private Retreat
Rosewood Castiglion del Bosco is a castle-like getaway with a Michelin-starred restaurant and world-class wines.
Roll along a seemingly endless cypress-lined drive and you’ve entered the Rosewood Castiglion del Bosco, a beauteous luxury destination retreat in the pastoral countryside of Val d’Orcia, southern Tuscany. A collection of Medieval castles, ancient villages, vineyards, wineries, olive groves, fields of golden grain and sunflowers, this year the Castiglion del Bosco upped its already non pareil game.
Here you can walk in the hallowed footsteps of the iconic Ferragamo family, while hanging your Borsalino in one of eleven restored historic, private villas within the fashion house’s one-time country estate-turned five-star resort, which retains the feel of a private compound. New interior design updates and a plethora of cool new experiences have made this into the area’s top luxury hospitality draw.
Nine of the property’s eleven private villas within the estate are restored 17th and 18th century farmhouses, “restyled to provide modern luxury while maintaining its comfortably sophisticated Sienese footprint.” The epitomy of private residency, the villas are each singular in their décor and design. All boast their own heated infinity pool, terraces and gardens, and state-of-the-art kitchens, designed by Florentine tastemaker Riccardo Barthel in classic Tuscan country house style.
As an additional adventurous new amenity added this year, each of the residences is equipped with a Land Rover Defender or 4X4 off-road vehicle to cruise the region’s verdant landscapes, villages, and serene Orcia River valley. The entire sprawl of 2,470 acres is situated in the Val D’Orcia Natural Park, and is protected as a UNESCO World Heritage Site.
While the famed Salvatore Ferragamo luxury brand was founded in 1927 in Florence, and the family bought the estate in the 1970s, the Castiglion del Bosco’s origins date back 900 years. Besides its stellar restaurants (one of which earned a coveted Michelin star just this year), spas, and insurmountably distinct suites, the property holds the 1100 AD ruins of a castle, a medieval 14th century church and village. If guests aren’t history buffs, they’ll become converts. And the Ferragamo family still maintains ties to the property making sure their impeccable aesthetic traditions are carried on.
A Mecca for both gastronauts and oenologists, the Rosewood Castiglion del Bosco calls home two haute cuisine restaurants, the Osteria La Canonica and the Michelin-starred Campo del Drago Restaurant, both helmed by Chef Matteo Temperini. Osteria La Canonica nods in menu and setting to an authentic Tuscan trattoria. The Campo del Drago Restaurant serves original dishes made with that abundance of locally sourced organic produce: tradition meets innovation. Most menus are seasonal and based upon the freshest of availability.
The chef makes his picks from the Borgo’s organic vegetable garden. Guests can experience it all by taking the in-house cooking school and learn about those reds at its winery. (Take a breather and a Sambuca at any of the estate’s three character-rich bars; two are poolside.) Dinner in the organic garden is a given, simply for the panoramic view of Montalcino. The expansive vegetable garden provides the herbs and vegetables used in the two restaurants.
Wine lovers, take note (or notes). This is where the fabled Brunello di Montalcino is produced, “a refined ruby red, intense and complex, with golden yellow and burgundy nuances, all of which evoke the bright colors of the vineyards illuminated by the sun in autumn.” The Castiglion del Bosco winery hosts a multitude of experiences and activities related to tasting.
A highlight is September’s annual grape harvest festival. Castiglion del Bosco is a historic winery and the fifth largest producer of Brunello di Montalcino. Winemaker Cecilia Leoneschi oversees harvesting, a two-step process of manual selection and aging in barrels, within the vacuous cellar. You can visit the various winemaking and wine-oriented hospitality offerings, and see for youself why they have garnered so many awards.
Want to work it off? The estate’s spa is suffused with earth tones and natural shades, and is an essential link in Rosewood Castiglion del Bosco’s health-and-wellness program. There’s a gorgeous swimming pool with views of the rolling hills and vineyards. Plus an exclusive 18-hole golf course next door designed by Tom Weiskopf, which is is the only private golf club in all of Italy. Guests of Rosewood Castiglion del Bosco have privileged access.
If excursions are your thing, there are several new ones to hop on: take a helicopter on Fly Brunello from the resort to Val d’Orcia, choppering over the Brunello region, encompassing the villages of Montalcino, Pienza and Montepulciano, where vineyards mix with picaresque landscapes. This experience includes a private visit to a dynamic duo of wineries: Podere Le Ripi and Castiglion del Bosco. Day-trippers will also lunch at the Michelin-starred restaurant Il Silene on Monte Amiata.
Or guests can road trip to nearby Siena to see the sights, or to Florence in a resort-planned excursion, which begins at the Castiglion del Bosco Wine Lounge, inside Palazzo Cappon, then continues to the Ferragamo Museum, dedicated to the founder of the fashion house, famous for its soles and soul. The current exhibition, “Salvatore Ferragamo 1898-1960,” is a tribute to the founder of the eponymous brand. The exhibition recalls the first retrospective on Ferragamo presented in 1985 at Palazzo Strozzi, Florence. Upon request, book a personal shopping service at the Ferragamo boutique in Via dei Tornabuoni.
The resort in recent years has been presented numerous awards: the Campo del Drago Restaurant (for its Michelin star in 2024), as well as those from 2 Forchette, Gambero Rosso’s 2024 Italian Restaurant Guide; Rosewood Castiglion del Bosco (included in 50 Best Discovery); and a five-star rating this year by the Forbes Guide. In the Rosewood Hotels & Resorts platform, the estate is not alone in the highest standards of hospitality. It includes 33 one-of-a-kind luxury hotels, resorts and residences in 21 countries, from New York City to China.
