Billionaires are unleashing their private jets and superyachts to prepare for the holiday season, which is sending many off to familiar hot spots.
Every December, the richest of us decamp to expensive destinations for some quality time with family and friends – often other billionaires.
This year will be no exception.
“It’s going to places that are exclusively pretty much high net worth,” Winston Chesterfield, the founder of Barton, a consulting firm focused on luxury and the wealthy, told Business Insider. “They want these private resorts away from everyone else because they don’t want to be around everyone else.”
Already, many of the world’s largest yachts have fled to warmer waters.
According to the ship tracker Marine Traffic, Jeff Bezos’ yacht, Koru, and Barry Diller’s Eos are floating in the Caribbean Sea. Eric Schmidt’s Whisper is heading to Barbados, while Len Blavatnik’s Odessa II was last spotted docked in Antigua.
Once their billionaire owners board, several of these ships will likely make their way to St. Barts.
“I always say if you want to have your toes in the sand and eat a croissant that feels like you’re in Paris, St. Barts is the place for you,” Elisabeth Brown, the membership director at the luxury concierge service Knightsbridge Circle, told BI.

Last year, Bezos, his fiancée, Lauren Sánchez, and Michael Jordan were photographed on St. Barts, and David Geffen’s superyacht, the Rising Sun, was spotted in the vicinity.
For those who don’t spend their nights on yachts, luxury hotels like Eden Rock and Cheval Blanc, owned by the billionaire Bernard Arnault’s LVMH, are going for upwards of $5,000 a night for a room at this time of year.
The cheaper hotels aren’t exactly low budget — which is part of the allure. A night at the least expensive hotel of the week between Christmas and New Year’s can be more than $3,000 a night.
“There is nothing mass-market about it,” Chesterfield said. “It’s impossible to be there unless you are really wealthy.”
Some superrich travelers look further north for their fun, opting to embrace colder temperatures.
“The holidays in the mountains are more of an escape than any other holidays, even escapes to their own remote private islands and things,” Chesterfield said.
In Europe, that translates to the Alps. Gstaad, St. Moritz, Courchevel – a favorite of the Russian oligarchs- and Val-d’Isère are some classic ultrahigh-net-worth favorite places to go during winter according to Chesterfield and Brown.
Chesterfield said he’s seen some choose quieter destinations lately, such as Crans-Montana in Switzerland, where the billionaire Vicky Safra has a home, or Kitzbühel in Austria.
“You’re less likely to bump into people that you know there,” he added.
Some of the most well-off have eight-figure chalets that they rent out for as much as $40,000 a week in peak season. Real-estate prices are climbing in these places too: homes in Gstaad, the priciest locale, cost 41,500 euros, or about $43,350, per square meter, Knight Frank’s 2024 Alpine Index reports.
Buying luxury condos within resorts, like the Six Senses in Courcheval, is also becoming more commonplace, largely due to amenities that can include spas, saunas, ski valets, and concierges.
Aspen, of course, remains the ultimate stateside ski resort.
According to a 2023 study by the data firm Altrata, this town has the highest concentration of residents whose net worth exceeds $30 million. Among its residents are billionaires such as Steve Wynn, Daniel Och, and Terry Taylor, while pictures of some of the most affluent celebrities in town have emerged in recent years while taking holiday downtown shots of Rihanna and Kylie Jenner.
“It’s the closest you’ll get to a European après situation,” Brown said. “Great mountains, great skiing, the hotels are top-notch, the restaurants are awesome.”
There’s a restaurant by the chef Nobu Matsuhisa, designer shops like Prada and Gucci, and private clubs to make the überrich feel at home. Plus, there are plenty of top resorts like the St. Regis and Little Nell, where rooms cost four figures a night.
Of course, sometimes billionaires are just like us — at least kind of. One of Brown’s clients is gifting their family a trip to Disney World, though it will cost more than the typical American family’s vacation to Cinderella Castle.
“It’s a few days, for about seven or eight people,” Brown said. “It’ll probably end up being $75,000, give or take.”