Associated Artists Gallery, Southport

MONTALCINO, Italy “The best things happen by chance.”

Massimo Ferragamo still marvels at his fortuitous first visit to the small town of Castiglion del Bosco and how this blossomed into a luxury project nestled in Tuscany’s Montalcino, in the heart of Val d’Orcia, around 23 miles from Siena and 65 miles from Florence.

As chairman of Ferragamo USA, a subsidiary of the Florence-based Salvatore Ferragamo company, he has been living in the U.S. for the past 20 years, but admits his “heart continues to beat for Tuscany.” Looking for a house in the region with the goal of producing wine, only the Brunello di Montalcino area would do. “Frankly, it’s the most beautiful part of Tuscany and one of the most prestigious brand names for wines in Italy,” he contends.


Massimo Ferragamo 

He started looking at houses and vineyards covering about seven acres. Instead, he ended up buying almost 5,000 acres that include a medieval hamlet with a 14th-century church containing a fresco by Pietro Lorenzetti; the ruins of a fortress, whose stylized tower is now also the venue’s logo, and 20 farmhouses.

“When I first saw it, I was speechless not only because of the size of the property, but also because of its layout. There was nothing that disturbed the view in any direction; you felt as if you were back in the Middle Ages. Nothing has changed, it’s incredibly green and despite the previous five owners over the past 20 years, the property had never been parceled out,” explains Ferragamo, in his laid-back and friendly manner.

Castiglion del Bosco

The Capanna vineyards at Castiglion del Bosco.  Courtesy Image

Ferragamo restored the hamlet and the farmhouses, which were dilapidated and used as tool sheds, but the vineyards were in the right spots, although he had to replant half of them. Today, Castiglion del Bosco is the fifth largest producer of Brunello di Montalcino, with almost 150 acres of vineyards, out of the 240 makers of the famed and prized wine.

Ferragamo saw the potential of what he thinks was a “diamond in the rough” and has developed it to include a private, by-invitation-only golf club designed by golf champion Tom Weiskopf, winner of the British Open, and a club house.

“Tom is very talented and adapted the course to the hills, without ruining the land,” Ferragamo observes of the expansive 444-acre, 18-hole course. There are 100 members belonging to the club — and beyond the beauteous surroundings, there are other perks. Any player who gets the 19th hole in one receives a Magnum of Brunello, although this has only happened twice so far, he says. While Ferragamo prides himself on the privacy allowed to guests, former President Obama’s visit with the American ambassador to Castiglion del Bosco in May made news here. Fifty percent of the resort’s guests are Americans, says Ferragamo, but Asians are also beginning to visit.

Hiking, biking and a cooking school are other activities offered, as well as a gym and a spa as part of the hotel and villas.

Beyond the golf club, Castiglion del Bosco includes a five-star hotel, comprising 23 suites and 11 out of the 20 farmhouses from the 17th and 18th centuries restored as villas by interior designers Chiara Ferragamo, Massimo’s wife, and Teresa Bürgisser Sancristoforo. Each villa is different, characterized by special details as the two interior designers worked with local artisans and producers, using Carrara marble or travertine with veins the color of wine, for example, and luxurious textiles and bed linens from C&C Milano. “Guests should feel comfortable, as if they already knew the place, without it being too traditionally Tuscan,” says Ferragamo.

Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco  Durston Saylor

The villas have between three and six bedrooms, big fireplaces and each includes a private heated pool. Daily rates for a villa in winter start from 2,500 euros for a minimum stay of three nights, and include daily cleaning, security 24/7 and concierge, plus, with the full optional service, a dedicated maid and a chef.


Villa Sant'Anna. Castiglion del Bosco

Villa Sant’Anna at Castiglion del Bosco.  Matteo Carassale

At the hamlet, near an organic vegetable garden, there is a restaurant and a trattoria, where an oven-baked pizza is a must, headed by chef Enrico Figliuolo. In high season, the resort employs between 220 and 240 people.

While Ferragamo invested in the hamlet in 2003, Castiglion del Bosco didn’t open for business until 2008. “I could write a book about wrong timing,” he laughed, pointing to the early signs of the global recession at that time. Starting in 2015, Ferragamo partnered with Rosewood Hotels and Resorts, which manages the hospitality and not the golf course and the vineyard. According to Ferragamo, Rosewood’s luxury is not standardized and “is not ostentatious, so it fits with Tuscany, and puts guests in touch with the region. After all, their tag line is ‘a sense of place,’ which is what I would like to offer.”

The golf course and the activities connected to the vineyard remain open year-round, including the wine club, which looks like a luxurious library where members store their own bottles — a peek shows cellars labeled Frédéric Fekkai, the beauty entrepreneur, as well as Justin Timberlake and Jessica Biel. While the hotel usually closes from mid-March to mid-November, for the second year the villas will remain open through the winter.

Although Ferragamo’s brother Ferruccio has invested in the winemaking estate and resort Il Borro Relais and the Ferragamo family, including the two siblings, has developed the Lungarno Collection of hotels in Florence, Castiglion del Bosco is an entirely separate business and none of the ventures plays the Ferragamo name’s card.

“This was a very specific project. When I first saw Castiglion del Bosco, it’s as if it was asking for help,” says Ferragamo.