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Best Luxury Thanksgiving & Christmas Getaways 2025

Luxury Thanksgiving getaways are not just about the destination – they’re about creating private, unforgettable moments with the people who matter most.

For me, the holiday season is more than just a celebration. It’s the moment to slow down, reconnect, and create memories in extraordinary places. Every year I see more and more travelers searching for exclusive escapes that offer both privacy and luxury. Think private villas on the beach, Alpine chalets with heated pools, or a glamorous city break with VIP perks.

At Travel WorldClass, I design every journey with one thing in mind: making your Thanksgiving and Christmas holidays unforgettable. Here are my favorite destinations for 2025. Whether you’re traveling as a couple, with family, or looking for a once-in-a-lifetime festive experience.

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ALPINE CHALETS IN ASPEN & ST. MORITZ

There’s something magical about spending Thanksgiving or Christmas surrounded by snow-covered peaks.

Aspen, Colorado is one of the most searched-for destinations for luxury holiday escapes in the U.S. – and for good reason. The town transforms into a winter wonderland with festive lights, boutique shopping, and world-class ski slopes. Families love it for the cozy mountain chalets with private fireplaces and ski-in/ski-out access, while couples can enjoy spa treatments and après-ski champagne in style.

St. Moritz and Courchevel in Europe bring a different kind of glamour – where heli-skiing, Michelin-starred dining, and private mountain guides turn the Alps into your playground. Booking a private chalet here means a personal chef preparing Thanksgiving dinner or a Christmas feast in the privacy of your own alpine retreat.

With Travel WorldClass Travel Design, I make sure your chalet comes with VIP touches: ski passes arranged, private instructors booked, and festive dinners created just for you.

PRIVATE VILLAS IN THE CARIBBEAN

The Caribbean remains one of the top searched regions for private villas during the holidays. If snow isn’t your style, you can trade it for palm trees and turquoise waters.

  • St. Barts is perfect for couples looking for jet-set glamour. Villas here often come with infinity pools, clifftop views, and direct access to chic beach clubs like Nikki Beach.

  • Turks & Caicos and the Bahamas are ideal for families, with spacious beachfront estates where children can play freely while adults enjoy spa services or sunset cocktails.

  • The Dominican Republic has become a hidden gem for private estates and golf retreats, offering great value compared to more traditional luxury islands.

Imagine a Thanksgiving dinner served on your private terrace by a personal chef, or a Christmas morning waking up to the sound of waves instead of snow.

With Travel WorldClass, I unlock villas not listed on public booking sites, and ensure extras like yacht charters, private chefs, and festive beach dinners are all part of the experience. More information here.

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FESTIVE CITY BREAKS IN NEW YORK & LONDON

For those who love the sparkle of the season, nothing compares to a city escape.

New York City is iconic during Thanksgiving: the Macy’s Thanksgiving Day Parade, ice skating at Rockefeller Center, and holiday shopping on Fifth Avenue draw visitors from around the world. For Christmas, the entire city glows – from the famous Rockefeller Christmas tree to luxury hotel displays at The Plaza, Baccarat, and The Peninsula. Families can enjoy festive shows like The Nutcracker, while couples book romantic suites with skyline views.

London is just as enchanting at Christmas. Think sparkling lights along Regent Street, festive markets at Hyde Park’s Winter Wonderland, and the most luxurious afternoon teas at Claridge’s or The Connaught. While Thanksgiving is less traditional in the UK, many five-star hotels now offer private Thanksgiving dining experiences for American guests – and I can make sure you have the best table.

Through Travel WorldClass, I secure prime viewing spots for the parade in NYC, sold-out holiday shows in London, and insider restaurant bookings that make city holidays completely seamless. Request here.

PRIVATE VILLAS IN THE U.S. IN PALM SPRINGS & FLORIDA KEYS

If you prefer to stay closer to home, two of the most searched-for U.S. holiday villa destinations are Palm Springs and the Florida Keys.

Palm Springs is perfect for couples seeking a chic, sunny escape. Private villas here often feature mid-century modern architecture, desert mountain views, and heated pools – ideal for Thanksgiving by the pool with champagne instead of turkey in the oven.

The Florida Keys are beloved for family holidays. Large oceanfront villas offer space for multi-generational travel, with private docks, yachts, and access to snorkeling or diving trips. It’s one of the few U.S. spots where you can combine Christmas festivities with a tropical climate.

Booking through Travel WorldClass means your villa comes with VIP perks – from private chefs who prepare holiday feasts, to spa treatments and yacht excursions arranged down to the last detail.

WHY BOOK NOW?

The truth is simple: the world’s most exclusive escapes book out fast. Thanksgiving and Christmas are peak travel moments, and the most beautiful villas and chalets are gone months in advance.

Booking with Travel WorldClass means:

  • VIP perks at top hotels & villas.

  • Insider connections – from Michelin-starred tables to yacht charters.

  • 24/7 personal support.

  • Luxury, designed around you.

Thanksgiving and Christmas are the moments that matter most – and where you spend them makes all the difference. Whether it’s a snow-covered chalet in the Alps or a private villa in the Caribbean, I’d pleased to design your holiday journey with the exclusivity and elegance it deserves.

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Ready to plan your next luxury escape?
With in-depth knowledge and strong connections to the world’s most exclusive hotels, I’ll ensure every detail of your journey is seamless and unforgettable. Discover more on my travel advice page

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