Italy has inspired and perfected the art of “la dolce vita” or “the sweet life.” With legendary hotels and resorts scattered across Europe, it’s perhaps no surprise that Italy is home to the continent’s best resort. Castiglion del Bosco, A Rosewood Hotel, was voted No. 1 resort on the continent in Travel + Leisure’s World’s Best Awards 2026. The retreat is located near Montalcino in the Val d’Orcia, a UNESCO World Heritage Site renowned for its sweeping hills, cypress-lined drives, famed vineyards, and centuries-old Tuscan towns.
The history of Castiglion del Bosco, A Rosewood Hotel, dates back nearly a millennium, when it was a medieval fortress and hilltop village. The Ferragamo family, known for the Italian fashion house of the same name, purchased the sprawling estate in 2003 and transformed its stone buildings and farmhouses into a luxury resort with over 40 suites and 11 private villas. The property maintains its traditions of winemaking and agriculture with acres of vineyards, farms, and gardens. Its restaurants — including one with two Michelin stars – serve farm-fresh Italian cuisine, while the on-site vineyards and winery harvest and bottle Brunello di Montalcino wine. Castiglion del Bosco also brims with classic resort amenities, including swimming pools, an 18-hole golf course, and a spa. While the 5,000-acre estate offers plenty to do, there’s a ton more to discover in the surrounding Tuscan landscape, from charming cities to natural hot springs.
Castiglion del Bosco is about a three-hour drive from Rome and roughly two hours from Florence. Villas are available to rent year-round, while the resort closes for the winter between early January and mid-March.
Staying and dining at Castiglion del Bosco, A Rosewood Hotel
To experience Europe’s best resort for 2026, guests can check into the resort’s accommodations, split between spacious suites and private villas. The suites are designed in a warm color palette with Tuscan touches, including wood-beamed ceilings, botanical art, and views of the Val d’Orcia countryside. Some suites even have private terraces from which to enjoy morning coffee or an evening aperitivo.
Groups seeking more space can book one of the villas, which are centuries-old stone farmhouses redesigned into luxe escapes. These multi-bedroom abodes feature private swimming pools, full kitchens, outdoor patios for alfresco meals, and a 4×4 vehicle for exploring the surrounding countryside.
The region’s bounty is on full display at the resort’s duo of restaurants, both overlooking the Val d’Orcia. The two-Michelin-starred Ristorante Campo del Drago serves multi-course tasting menus of innovative Tuscan cuisine with ingredients sourced from the on-site kitchen garden. For a more relaxed trattoria-inspired experience, Osteria La Canonica offers local Italian favorites, such as risotto with Montalcino saffron, fire-roasted pizza, fried veal chop, and Tuscany-spiced lamb sausage. “Enjoying dinner as the sun set over the vineyards was one of the most memorable moments of our trip,” raved a Google reviewer. Even if you’re not a guest of the hotel, you can still reserve a table at either restaurant to sample the estate’s cuisine and Brunello di Montalcino wines. During the warmer months, the resort also hosts Festa della Domenica, a weekly dinner party held from late June through late September. Guests dine under a canopy of fairy lights while enjoying Tuscan specialties and wine served in the historic village square.
Activities and amenities at Castiglion del Bosco, A Rosewood Hotel
Set amid the UNESCO-listed Val d’Orcia, a region known for its food, wine, and views, Castiglion del Bosco offers a seemingly endless array of activities and adventures. Guests who simply want to relax can lounge by the hotel’s main infinity-edge Borgo pool or the Silent Pool, both of which overlook the rolling countryside. For even more pampering, the hotel’s spa offers indulgent treatments inspired by Tuscany’s herbs, wine, roses, and more. Golfers can tee off at the property’s private 18-hole golf course, while bikers and hikers can conquer the hilly trails that weave through the 5,000-acre estate.
Wine enthusiasts will want to visit Castiglion del Bosco Winery to tour the over 150-acre vineyards and sample Brunello di Montalcino produced on-site. At La Canonica Cooking School, foodies of all ages can learn Italian cooking techniques. Participants tour the property’s kitchen garden to pluck herbs and vegetables before preparing homemade pasta, pizza or pastries.
The resort is also an ideal base for exploring Tuscany, where you can cruise down cypress-lined lanes past centuries-old farms and villages. Less than an hour’s drive from the resort is Siena, a charming, history-rich city in Italy that’s considered the friendliest in all of Europe. The city is famous for its Palio di Siena, a centuries-old horse race held every summer in the central Piazza del Campo square. After exploring Siena, take a break from the city’s crowds and drive about 30 minutes away to Petriolo, secret natural hot springs that offer an idyllic respite.
