Castiglion del Bosco

Courtesy Castiglion del Bosco

DEPARTURES published a first look at Massimo Ferragamo’s over-the-top Italian estate, Castiglion del Bosco, in September 2008—the same month that Lehman Brothers disintegrated and took the global economy down with it. Six years later, the financial markets have rebounded, and so has the property. On a recent late afternoon at the resort, Ferragamo tells Julian Sancton about his evolving vision.

Sipping a glass of Brunello di Montalcino, surrounded by family, Massimo Ferragamo is surveying one of the most sublime landscapes in Tuscany. From the main terrace of Castiglion del Bosco, the medieval village he transformed into a rustic luxury retreat, he spots something grazing in a meadow below, pauses midsentence, and squints. Wild boar? No, deer. The avid hunter taps Marco Battaggia, his brother-in-law and the landscape designer of this 5,000-acre property, on the shoulder in a conspiratorial manner. To Massimo’s right is his elegant, athletic wife, Chiara, who helped oversee the hotel’s decoration. They are joined by their teenage son, Giacomo, on summer break from high school in the United States. Massimo seems to bask in the profound happiness of a dream fulfilled—and not easily so.

It was this Brunello, from the property’s vineyards, and this vista that first drew Massimo to Castiglion del Bosco 15 years ago. “There are few views that really stay in your mind,” says Massimo, who runs the U.S. operations of the iconic fashion brand founded by his father, Salvatore. “This one did.” Massimo’s original intention when he acquired the land, in 2003, was to turn it into what he calls a “private-residence club,” where a curated membership consisting of friends and friends of friends would pay dues and have yearly access to a villa in Tuscany without the constant headaches of actually owning a villa in Tuscany.

He spent five years restoring the town and surrounding farmhouses, which had operated essentially as a feudal estate for 800 years, retrofitting them with every comfort the sophisticated traveler has come to expect. He built a state-of-the-art winery and set up Italy’s only private golf club, with 18 holes designed by in-demand course architect Tom Weiskopf.

Massimo’s initial plan, however, would become a casualty of the global financial crisis. “We opened in June 2008,” he says. “So that timing was maybe, from an economic point of view, the worst.” He ran with it for a while, selling a few $2 million memberships, and was hopeful that this business model could work. But he soon ran into two obstacles: First, the general slowdown of the luxury market meant that there weren’t enough members to justify the large staff. Second, Italy’s byzantine land-use laws made such an equity-sharing membership prohibitively complex. “It was quite apparent that we couldn’t have gone on with that formula and that we had to change,” says Massimo.

Today Castiglion del Bosco is open to the public. In addition to the 23 suites in the old village, or the borgo, 10 fully restored villas, each with its own heated outdoor pool, are available to guests. Massimo has also put several villas on the market and sold three so far. Perks of ownership include access to the wine club and the golf club (which has remained private) as well as Castiglion del Bosco’s staff. “We take care of everything from the service point of view but also from the maintenance point of view,” says Massimo.

In 2014 Castiglion del Bosco’s occupancy was more than what they had budgeted, to the point where they had to turn away business. Massimo is now thinking of building more suites and extending the open season. (The property will remain closed during the dreary winter months.)

In January, Castiglion del Bosco became a Rosewood property. Meanwhile, Massimo’s vision continues to evolve: “Whenever you fulfill a dream, you have some other ones that pop up.” This statement betrays Massimo’s Italian romanticism and also his fastidious perfectionism, the subject of much teasing over a family dinner at the property’s excellent restaurant, Campo del Drago. “Basically I would like to see [Castiglion del Bosco] tied to a few other properties in Italy,” he says. “Maybe that’s something we could be looking into— to not only own a great experience in Tuscany but also own a great experience in Italy.”

Suites start at $590; villas, at $2,430; Montalcino; 39-57/7191-3001;

The Villa to Rent

It's impossible to go wrong with any of the villas, but our favorite is the five-bedroom Villa Sant'Anna, which has a fabulous view of the estate's vineyards. The main house, which sleeps nine, features a large Tuscan fireplace and a tennis court. Available through November 14. From $4,980.