![Luxury Holidays [Adobe]](https://www.chicstylecollective.com/wp-content/uploads/2025/07/Chic-Style-Collective-Hero-Image-307-960x650.jpg "Chic Style Collective | Where Do the Rich Holiday? The Luxury Holidays Favoured by the Ultra-Wealthy 2026")
The best luxury holidays to book now
When it comes to travel and luxury holidays, the ultra-wealthy don’t just book a flight and check into a hotel—they charter private jets, buy out entire resorts, or retreat to estates only accessible by helicopter. For billionaires, celebrities, royals, and old money families, luxury travel is not just about location—it’s about privacy, prestige, and peerless service.
So, where exactly do the rich holiday in 2025? Below, we explore the luxury holidays that top the travel lists of the elite.
1. St. Barts – The Caribbean Playground of the Billionaire Set
A long-time favourite of the international jet set, St. Barts is where superyachts gather over New Year’s and designer kaftans rule the beach clubs. With just enough French flair to feel chic and the exclusivity of a private Caribbean island, this is a magnet for names like Jeff Bezos, Beyoncé, and the Kardashians.
Where to stay: Eden Rock, Cheval Blanc, or a private villa perched above Gouverneur Beach.
2. Lake Como, Italy – Old Money Elegance in the Alps
Few destinations exude quiet luxury like Lake Como. With historic villas, dramatic mountain views, and an impossibly elegant pace of life, it attracts Hollywood royalty and European aristocrats alike. Think George Clooney sipping espresso on his lakeside terrace or the Agnelli family mooring vintage Rivas by the dock.
Where to stay: Villa d’Este, Passalacqua, or a privately owned 18th-century palazzo.
3. The Hamptons, USA – Summering East Coast Style
For America’s elite, the Hamptons remains a summer tradition. More than just beaches and white picket fences, it’s about legacy homes, invitation-only soirées, and social cachet. From East Hampton estates to Sag Harbor sailboats, this enclave is where Manhattan’s old money escapes July heat.
Where to stay: Renting a heritage home on Georgica Pond or checking into the Topping Rose House.
4. Courchevel 1850, France – The Most Luxe Ski Resort in the World
In winter, the wealthy head to Courchevel 1850 for perfectly groomed slopes and champagne-fuelled après-ski. Russian oligarchs, royals, and tech founders favour its ski-in/ski-out chalets and ultra-luxe boutiques, including Chanel and Louis Vuitton with their own skiwear lines.
Where to stay: Les Airelles, Cheval Blanc Courchevel, or a private catered chalet with full staff.
5. The Maldives – Private Islands and Underwater Suites
When privacy is paramount, the Maldives is unmatched. With its constellation of private island resorts, you’ll find A-listers and billionaires in overwater villas with their own butlers, chefs, and plunge pools. Discretion is key—many guests arrive barefoot and stay off social media.
Where to stay: Velaa Private Island, Cheval Blanc Randheli, or The St. Regis Maldives Vommuli’s private residence.
6. Aspen, Colorado – Where Wealth Meets Wilderness
Aspen blends rugged alpine beauty with designer ski fashion, Michelin-starred restaurants, and serious real estate. From snowboarding billionaires to New York media moguls, Aspen is the American winter escape of choice. The social scene is as hot as the après-ski cocoa.
Where to stay: The Little Nell, Hotel Jerome, or your own multi-million-dollar ski chalet.
7. Amalfi Coast, Italy – Mediterranean Glamour Reimagined
For the stylish and the storied, the Amalfi Coast is irresistible. Its winding roads, lemon groves, and pastel cliffside towns attract yacht owners, fashion insiders, and old European money. It’s not uncommon to spot Valentino’s yacht docked off Positano or a Vogue shoot at Villa Treville.
Where to stay: Le Sirenuse, Villa Cimbrone in Ravello, or chartering a yacht along the coast.
8. Dubai & Abu Dhabi – The New Age of Hyper-Luxury
For those who equate wealth with scale, Dubai and Abu Dhabi offer gold-leafed hotels, designer malls, and desert resorts with falcons on hand. It’s luxury amplified—Rolls-Royces in the hotel driveways, Michelin-starred dining in the sky, and bespoke experiences on demand.
Where to stay: Bulgari Resort Dubai, Emirates Palace Mandarin Oriental, or the Royal Suite at Burj Al Arab.
For the ultra-rich, holidays are about more than just location—they’re about exclusivity, experience, and escaping the ordinary. Whether it’s a chalet in the Alps, a villa in Italy, or a private island in the Indian Ocean, the wealthiest choose destinations that reflect their personal taste and protect their privacy. Because when money is no object, the world is not just your oyster—it’s your private jet runway.
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