NOW: Castello di Casole has been in existence in one form or another for some 300 years.
Courtesy Timbers Resorts

We are scouting for boar on the private game preserve of the Castello di Casole, a ­medieval castle turned luxury hotel in Italy’s famed Tuscany region. But some members of our party (i.e., me) overslept, and as the faint glow of sunlight spreads above the soft green hills, our opportunity to see a boar — or cinghiale, as it’s known in these European parts — dims; the creatures are nocturnal. Nonetheless, we stare out the mud-splattered windows of our vehicle in hopes of spotting the legendary beast foraging for truffles in the dark woods, but the only thing we catch is a trespassing poacher looking shifty-eyed on the side of the road. Our driver, Claudio, one of several game wardens employed by the Casole, immediately pulls to a stop and radios security. There’s an edge to his voice, and even though I don’t speak fluent Italian, I understand enough to know the poacher is in deep cinghiale scat.

A few minutes later, we’re once again bumping along the dirt roads of the 4,200-acre Northern Italy estate, past forests and fields, olive groves and vineyards, until we ascend the hotel’s long driveway hemmed by towering cypress. The hunt is over, but the day is just beginning on this emerald hilltop property less than an hour’s drive from Florence, Siena and the walled city of San Gimignano.

In 2005, Colorado-based Timbers Resorts bought the Castello di Casole, which was built in the 1700s atop the ruins of a 10th-century castle, and transformed it into a 41-suite hotel that opened last July. Original materials found on the estate were used in its restoration, and the result is a


Castello di Casole
Località Querceto
53031 Casole d’Elsa
Siena, Italia
(888) 548-9429
charming, Tuscan-style complex with exposed stone walls, vaulted arches, terra-­cotta tiles and wood-beamed ceilings. There’s also a spa and wellness center in the former barrel-ceiling wine cellar, three restaurants, the aforementioned game preserve and an infinity pool offering spectacular views of the sunset.

There’s much to love about the hotel, including opportunities to take early-morning yoga classes in the chapel, ride bikes along miles of wooded trail, oil-paint on the hotel terrace, take Italian cooking classes, get a jolt at the espresso bar, hunt for mushrooms and, of course, taste wine. Oh, how you taste the wine. The on-site, elegant Ristorante Tosca offers more than 250 varie­ties of Italian vino and an English-speaking­ ­sommelier to assist with food pairings. Executive chef Daniele Sera, who formerly worked as a personal chef to the King of Morocco, uses produce from the hotel’s gardens and extra-virgin olive oil made from groves on the estate to concoct incredibly fresh and creative meals, such as coffee-scented veal cheek with salty pine-nut toffee. He’ll even cook your boar if you catch one.

I sip my first glass of wine, a smoky Chianti, at the hotel’s Bar Visconti, named for the Italian filmmaker Luchino Visconti, who lived at the Casole during the 1960s. Best known for his 1963 film The Leopard, Visconti often used the estate to entertain the jet set, including actors Sophia Loren and Burt Lancaster. “It was the getaway for filmmakers and European stars — a lavish Hollywood pad,” says Gary Ross, Timbers’ director of architecture. The bar has a masculine feel to it, with dark-paneled walls, a black-and-white marble floor and gleaming brass accents.

I pour my second (or is it fourth?) glass of wine of the night from a bottle in my room. It’s one of the hotel’s private labels, crafted using a blend of grapes from the property’s 88-acre vineyard. The Dodici is silky and bold, and I carry the glass up a winding staircase to my four-poster bed in the castle’s stone tower. Built in A.D. 900, the tower is all that remains of the estate’s original structure, and I am lucky enough to have snagged this two-story suite for the next four nights.