Italy: Tuscany: Where to Stay: Most Indulgent: Castiglion del Bosco

Castiglion del Bosco

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. Castiglion del Bosco, in the rolling hillside of Tuscany’s Montepulciano region, is such a property.

Not incidentally, this special place is owned, and was designed by, 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, a sprawling hilltop estate that has been a passion project for family patriarch 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, Castiglion centers around a historic borgo, which now houses several suites and exquisite common spaces, as well as includes 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, Castiglion 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 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 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. When exploring the region, it helps to come from a place that’s Ferragamo-run. 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 easily be organized.

Says Massimo Ferragamo about what the property means to him: “Seeing a historical place come back to life with a real purpose, where wine-making, hospitality, sporting activities and agriculture all play a role to deliver a special experience to everyone who visits, is very satisfying for me. It’s been an honor to be a part of it.”

Who Should Stay: Only 90 minutes from Florence, Castiglion del Bosco makes a great stop in any Tuscany itinerary. It’s 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 4-5 nights.

Room to Get: While the suites in the Borgo are beautiful and great for couples, the spacious villas are the real treasure here. Especially families with children, friends traveling together or couples looking for a really unique hideaway should consider booking one of these. Indagare’s Monique Brendel visited in the fall of 2012 and is happy to share her favorites. (Contact our Bookings Team.)

Indagare Tip: Summer may be most popular, but fall is a great time to visit. In late September you have the grape harvest and all its wine-based activities; in November white truffle season lures connoisseurs to this area.

Read an interview with Massimo and Chiara Ferragamo about their Castiglion dream.

Read more member raves about Castiglion del Bosco.