WHERE TO STAY AND PLAY Ski families can get a head start on the season in the Aosta Valley, in Northwestern Italy. A high altitude gives the Alpine resort Breuil-Cervinia good snow as early as October, all against the backdrop of Monte Cervino, what Italians call The Matterhorn. The range of accommodations there include Aux Pieds Du Roi, a self-described “eco maison” with funky interior design and easy access to the lifts (rooms start around $461/night).

Farther south, in Rome, the Roma Jazz Festival runs from November 1 to December 1. Book one of the 18 art-filled rooms and suites at Hotel Vilòn, a renovated 16th-century palazzo; the hotel (from around $646 a night) will offer a Thanksgiving alla Romana dinner at Adelaide, its restaurant. Also in Rome, large families can rent dreamlike private accommodations — say, a palace with Italian Renaissance frescoes or a penthouse overlooking Piazza Venezia — from The Grand House and hire the Michelin-starred chef Cristina Bowerman to cook Thanksgiving dinner.

Finally, in the town of Fasano, in Puglia (one of The Times’s 52 Places to Go in 2019), three- and seven-day wellness retreats at Borgo Egnazia (from around $296 a night) include therapeutic sessions with a “Master of Laughter,” spa treatments and more. Around Thanksgiving, a twinkly holiday market opens in the resort’s on-site piazza. In Gagliano del Capo, visitors can immerse themselves in Apulian culinary traditions through orecchiette-making classes and vineyard and olive-grove tours at Palazzo Daniele. In November, rates at the new nine-suite boutique hotel, which is housed in a 150-year-old palazzo, start around $260 a night — less than half the summertime price tag.

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