Caribbean yachts, ski chalets, and private jets: how many billionaires spend Christmas

By the time Christmas week arrives, many billionaires and ultra-wealthy families aren’t deciding whether to travel—they’re deciding where to base themselves for a tightly managed season that often stretches from mid-December through New Year’s. The consistent theme is control: privacy, security, scheduling, and a curated experience that doesn’t depend on crowds or last-minute availability.

The warm-weather tradition: superyachts and private villas

For the billionaire set that wants sunshine in December, the Caribbean is a recurring favorite. The most talked-about hubs tend to be the places that can handle ultra-luxury demand at scale: top-tier villas, high-end hotels, yacht marinas, private chefs, security teams, and logistics crews that can make a trip feel “effortless.”

A typical Christmas-week Caribbean routine can look like this:

• Flying in privately, then transferring quickly to a villa or yacht

• Hosting small, invitation-only dinners rather than going out publicly

• Using a superyacht as both a luxury base and a way to disappear—anchoring off quieter coves when the main harbor gets crowded

• Island-hopping for variety: one stop for nightlife and restaurants, another for pure privacy

New Year’s is often the “main event” in this track—fireworks, harbor celebrations, and high-profile gatherings—while the days around Christmas can be noticeably quieter and more family-centered.

The winter version: ski towns built for the ultra-wealthy

For those who want snow, the holiday season often shifts to elite ski destinations where luxury real estate and high-end service are part of the local culture. The appeal isn’t just skiing—it’s the entire package: privacy, security, and a comfortable “chalet lifestyle” where everything is handled behind the scenes.

Common features of billionaire-style ski holidays include:

• Renting or staying in a private chalet with staff (chef, driver, housekeeping, sometimes security)

• Skiing early, before the busiest slopes, then retreating for private meals and spa time

• High-end après-ski that stays discreet—private rooms, member-only spaces, or in-home gatherings rather than packed public venues

• Short hops between multiple destinations, especially if weather or crowds shift

How they move: private aviation and tight scheduling

At this level, travel is often designed to minimize friction: flying at off-peak hours, landing at smaller airports when possible, and using chauffeured transfers or helicopters to skip traffic. Because holiday demand is heavy even for premium travel, many trips are planned far in advance—especially for scarce inventory like top villas, the best chalets, and prime marina access.

It’s also common for ultra-wealthy travelers to keep plans flexible, with backup options ready if weather, security concerns, or crowd levels change.

A quieter trend: wellness and retreat-style holidays

Not every billionaire holiday revolves around parties or ski scenes. A smaller—but increasingly visible—track is the retreat-style holiday: wellness resorts, meditation-focused getaways, and tightly structured “reset” trips aimed at recovery and mental clarity. For some, that’s a way to avoid the spotlight altogether while still treating the season as a major event.

The big picture

There isn’t one “billionaire Christmas.” But many holiday routines fall into a few repeatable formats:

• Warm-weather Caribbean trips centered on private villas and yacht life

• Snow-season getaways built around luxury chalets, skiing, and private social calendars

• Private, high-control logistics that reduce exposure and maximize comfort

• Selective visibility: some go public at New Year’s, but keep Christmas itself more priv