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“This season is a great time for really slowing down and enjoying the calm and quiet of Tuscany,” says Ferragamo, who enjoys brisk winter nature walks on the meandering unpaved roads of the surrounding Val d’Orcia region, making his way through the gentle hills and Sangiovese grape vineyards. After those walks, he finds that “the villas are the perfect retreat for painting, reading, and being inside with a fireplace, a good local Brunello wine, and good company.”

One of the bedrooms at Villa Stabbi.

Courtesy Rosewood Castiglion del Bosco

Here, Ferragamo shares a few favorite personal picks for what to do and see—and, of course, where to eat and drink—while you’re his guest.

“Many people assume fall’s harvest season is the best time to experience wine in Tuscany, but February is also exciting. That’s when we release the new vintage of the coveted red Brunello di Montalcino, celebrating its debut with two special events. Benvenuto Brunello welcomes the wines with two days (this year from February 19-22) of presentations and tastings, and the non-competitive Brunello Crossingrace (February 11-12) sees runners jogging through breathtaking countryside, stopping for guided tours of wineries that highlight the connection between sport, land, wine and food.”

“Adventurous travelers can try their hand at truffle hunting during the winter months. It’s thrilling to go out searching with local experts and their impressive dogs, and delicious tastings afterwards make this a delightful experience.”

“Driving around Tuscany is one of my favorite activities during the offseason—the crowds have disappeared, the atmosphere is festive, and the villages are filled with activity. Guests can use their villa concierge to book a trip to nearby towns by Vionic Kennedy Leather Block Heel Ankle Boots 64Ey1yen
, for a really Italian experience. My favorite stops include Etilivia Colorblock Sneakers maqT3a
, which boasts the region’s only Michelin-starred restaurant, Silene; and Pienza, one of Tuscany’s biggest and best producers of Pecorino cheese.”

“On a cool winter day, nothing beats a warmingglass of red wine. One of my favorite restaurants to visit and have a glass is Drogheria Franci, in Montalcino.”

“Travelers who are looking for unique and authentic items to bring back home should visit some of the wonderful local shops, especially wonderful to pop into when it’s cold outside: Pianigiani leather shop, in Buonconvento, for artisanal, made-to-order leather pieces; Montalcino 564 , in Montalcino, for a selection of high-quality Italian textiles; Enoteca La Fortezza , in Montalcino, for a wide selection of the best local and Italian wines; and Mulino Val d’Orcia , in Pienza, for organic pasta made from ancient, local grains.”

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