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Celebrate the Holidays in Italy at Rosewood Castiglion del Bosco

by Katie Skrzek

Nov 10, 2025

© Rosewood Castiglion del Bosco

Daily

Experience a taste of Tuscany this holiday season with a stay at Rosewood Castiglion del Bosco.

© Rosewood Castiglion del Bosco

Housed in a centuries-old estate in the heart of Brunello di Montalcino wine region, this property boasts an array of suites and villas perfect for individuals or groups. The property is home to two-Michelin-starred Ristorante Campo del Drago and Osteria La Canonica, as well as a cooking school. Play a round of golf at The Club, Italy’s only private golf club.

Festive season celebrations begin at Thanksgiving, with a special weekend full of culinary-focused offerings. Guests may participate in a truffle-hunting experience and a cooking class and wine tour at Castiglion del Bosco winery, and a delectable Thanksgiving dinner will be served. As part of Rosewood Hotels’ Sense of Place program, Rosewood Castiglion del Bosco lights up with a variety of special events, Nov. 27–Jan. 7. The property’s piazza transforms into a winter wonderland, complete with an ice skating rink, holiday market and visits from Santa Claus. Guests visiting on the holiday will delight in sumptuous Christmas Eve dinner, Christmas Day brunch and New Year’s Eve dinner.

In addition to the festive programming, Rosewood Castiglion del Bosco offers guests an array of curated experiences including horseback riding, stargazing sessions, cycling tours, wine tastings and more.

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