Experience the flavors and charm of Tuscany this holiday season with a stay at Rosewood Castiglion del Bosco.
© Rosewood Castiglion del Bosco
Set on a centuries-old estate in the heart of the Brunello di Montalcino wine region, Rosewood Castiglion del Bosco offers a refined selection of suites and private villas ideal for solo travelers, couples, and groups. The estate features two acclaimed dining venues, Ristorante Campo del Drago—recognized with two Michelin stars—and the more casual Osteria La Canonica, alongside a hands-on cooking school where guests can master Tuscan recipes.
Golf enthusiasts can enjoy The Club, Italy’s only private golf course on the property, while food and wine lovers will find abundant opportunities to explore the region’s renowned vintages through guided tastings and tours at the on-site Castiglion del Bosco winery.
Holiday festivities begin at Thanksgiving with a culinary-focused weekend that includes a truffle-hunting experience, a cooking class, and a guided wine tour, culminating in a special Thanksgiving dinner. As part of Rosewood Hotels’ Sense of Place program, the resort’s seasonal celebrations run from November 27 through January 7. The estate’s central piazza is transformed into a festive winter setting with an ice skating rink, a holiday market, and family-friendly visits from Santa Claus. Guests staying over the holidays can enjoy an elegant Christmas Eve dinner, a generous Christmas Day brunch, and a celebratory New Year’s Eve dinner.
Beyond the holiday schedule, Rosewood Castiglion del Bosco curates a variety of immersive experiences year-round. Options include horseback riding across the estate’s rolling hills, guided stargazing sessions under clear Tuscan skies, scenic cycling tours, cellar visits with expert-led wine tastings, and bespoke culinary activities. These curated offerings are designed to showcase the landscape, flavors, and traditions of the region while providing memorable, personalized moments for every guest.
Whether you seek a peaceful retreat, an active outdoor escape, or a food-and-wine focused holiday, Rosewood Castiglion del Bosco blends historic charm with modern luxury to deliver a distinctive Tuscan experience during the festive season and beyond.