Editors' Picks

Rosewood Castiglion Del Bosco

Grand estate, contemporary classic, immersive

Loc Castiglion Del Bosco, Montalcino SI 53024


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Indagare Adored

At a Glance

Take an Italian agricultural estate in Tuscany, complete with a winery and a historic village; add plush lodgings; and then pile on amenities—golf, tennis, spa, pool, fitness center. The result: Castiglion del Bosco. In 2003, Massimo Ferragamo (of the Salvatore Ferragamo clan) was scouring the Val d’Orcia for a parcel of land where he could produce his favorite Brunello di Montalcino wine. He visited the Capanna vineyards, and was so entranced by their beauty that he came away with a 5,000-acre estate. Eventually CDB was born, with the restored village serving as the hub for 42 rooms and suites, alongside a medieval church and 12th-century castle ruins. Amid the golden hillsides, the 300-year-old stone farmhouses now house 11 villas outfitted with contemporary comforts and private pools. Throughout, Ferragamo style and the handiwork of Florentine craftsmen shine, as do the local activities. During harvest season, you can even join in the grape-picking.

**The Standout:** Access to a superb winery making Brunello di Montalcino, from two vineyards, Capanna and Gauggiole **Don’t Miss:** Truffle-hunting in the woods with local experts and their adorable hounds

Indagare Loves

  • Every detail, from décor to activities, celebrates the surrounding Val d’Orcia
  • La Canonica cooking school and the organic garden
  • The priceless fresco by Pietro Lorenzetti, displayed inside the borgo’s tiny church
  • The 18-hole private golf club located within the estate, where Rosewood Castiglion del Bosco guests have privileged access


In an ever-flattening world, it’s becoming increasingly difficult to find those unique hotels that seem to not only be in a destination but to embody the very essence of a place. Rosewood Castiglion del Bosco, a serene Tuscan retreat in the rolling hillside of the Montalcino region, is such a property.

Not incidentally, this special place is owned, and was designed by Massimo Ferragamo, a member of one of Italy’s premier fashion families: the Ferragamos. The family name has long been synonymous with gorgeous leather goods and an artisanal, utterly Italian sensibility. This philosophy is also at the heart of Castiglion del Bosco, a sprawling hilltop estate that has been a passion project for Massimo Ferragamo and his wife, Chiara. Together they poured love, style, time and money into creating their vision of the ultimate Tuscan hideaway.

Only a 90-minute drive from Florence, Rosewood Castiglion del Bosco centers around a historic borgo, which now houses several suites and exquisite common spaces, as well as freestanding stone houses, all of which were lovingly restored and turned into villas. When it came to furnishing these spacious homes, Chiara Ferragamo and her interior designer went into overdrive, handpicking everything from the lavish fabrics to the antique furniture.

Each of the villas has its own distinctive look and feel, though all feature the inspired work of modern-day Florentine craftsmen. Take the memorable mini-bars, which are covered in sumptuous leather and embossed with the CdB logo. Incidentally, they are also a great example of style and function working together, as these set pieces are also stuffed with delicious local products. Thanks to the attention to detail, Rosewood Castiglion del Bosco is one of those rare places where guests feel as if everything has been considered for them in advance.

As beautiful and comfortable as the suites and villas feel, guests are also spoiled for choice when it comes to on- and off-property activities, all of which make the most of the region’s bounty. During the harvest, guests can sign up for a day in the vineyards, helping to pick the grapes and ending with an estate wine tasting and a hilltop picnic. In any season, food plays an important role in the CdB experience. The property has two bars and two restaurants, one more casual with incredible wood-oven pizzas, the other a more upscale affair. Vegetables and herbs come from the on-property garden, and guests are encouraged to stop by the kitchen, watch the chefs at work and make requests. Cooking classes are also available.

Exploring the region, too, is made easy. Whether it’s a private tour to the excellent Brunello wineries nearby or a falconry and archery adventure for kids, a host of experiences can be organized. The property also has a kids club, making it an excellent option for families.

Who Should Stay

Anyone looking for a resort-like experience wrapped in the full glory of Tuscany: Only 90 minutes from Florence, Rosewood Castiglion del Bosco makes a great stop in any Tuscany itinerary. It is such a special place that the biggest complaint we have gotten is that guests wish they had stayed longer. It can easily keep everyone entertained for four to five nights.

— Monique Brendel Thofte

Written by Indagare

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