Exclusive Escapes: Where the Ultra-Wealthy Will Spend Their Holidays

As Christmas holidays roll in, the world’s elite flock to luxurious destinations, carving out time with family amidst other billionaires. This year follows the same trend, with high-net-worth individuals gravitating toward secluded havens far removed from the masses.

Winston Chesterfield, founder of the luxury-focused consulting firm Barton, remarked that these affluent travelers seek exclusive resorts designed to keep them away from crowds. Warm-weather retreats are already buzzing, as many of the globe’s most opulent yachts have made their way to tropical waters.

In the Caribbean, vessels like Jeff Bezos’ Koru, Barry Diller’s Eos, Eric Schmidt’s Whisper, and Len Blavatnik’s Odessa II have been spotted navigating idyllic seas. These floating palaces often converge at St. Barts, a perennial favorite among the ultra-rich. Elisabeth Brown, membership director at the luxury concierge service Knightsbridge Circle, described it as the perfect blend of Parisian charm and beachside relaxation, where visitors can enjoy world-class cuisine with their toes in the sand.

St. Barts’ allure lies in its pristine beaches, high-end accommodations, and long-standing reputation as a playground for the wealthy. Esteemed families like the Rockefellers and Rothschilds established estates there decades ago, and it remains a magnet for modern billionaires. Last year, Jeff Bezos, Lauren Sánchez, Michael Jordan, and David Geffen’s superyacht Rising Sun were among the high-profile sightings.

For those preferring hotels, options like Eden Rock and Cheval Blanc, owned by Bernard Arnault’s LVMH, offer unparalleled luxury at upwards of $5,000 a night during peak season. Even the more “affordable” accommodations hover around $3,000 a night, ensuring the island’s exclusivity.

Meanwhile, some of the wealthy choose to embrace winter’s chill, trading sunny beaches for snow-capped mountains. In Europe, destinations like Gstaad, St. Moritz, Courchevel, and Val-d’Isère remain go-to spots for opulent alpine getaways. Winston Chesterfield noted that quieter ski towns such as Crans-Montana or Kitzbühel have gained popularity, offering privacy and exclusivity.

For those who prefer to buy instead of rent, high-end chalets in the Alps sell for astronomical sums, with properties in Gstaad reaching over $43,000 per square meter. Resort-based luxury condos, such as those in Courchevel’s Six Senses, are increasingly desirable for their lavish amenities, including private spas, ski valets, and concierge services.

Across the Atlantic, Aspen reigns as the premier destination for America’s elite skiers. Home to a dense population of ultra-high-net-worth individuals, the town attracts billionaires like Steve Wynn, Daniel Och, and Terry Taylor, as well as celebrities like Rihanna and Kylie Jenner during the holiday season. Aspen’s upscale restaurants, luxury shopping, and private clubs create an unparalleled après-ski experience, with accommodations like the St. Regis and Little Nell commanding top-tier prices.

Of course, even the wealthiest occasionally indulge in mainstream escapades. One affluent family reportedly chose Disney World for a holiday gathering, though their version of the trip—estimated at $75,000 for a group of eight—hardly resembles the average family vacation.

From private islands to posh ski resorts, the world’s billionaires continue to redefine the art of holidaying, proving that exclusivity is the ultimate luxury.

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