Ashley Isaacs Ganz was perplexed when she contacted a Swiss hotel on behalf of a client. He wanted to spend the holidays there with his extended family and needed several rooms and suites from December 23 through January 2. The property politely balked, explaining that this year, anyone wishing to stay over the festive break would need to commit to a minimum interested in staying during dates that are not convenient.”
This year, bolt-holes from Jackson Hole to Courchevel are imposing the same constraints—the Les Airelles property in the French Alps, for example, has a 14-night requirement—as are some five-star villas. “There’s a luxury ranch outside of Aspen that was ‘rates upon request,’ and they vetted the guest as well as the length of stay,” says Kevin Jackson of EXP Journeys, another Robb Report Travel Master. Hotels in the other winter-season hot spot, the Caribbean, are no less greedy. Both Sandy Lane in Barbados and Antigua’s Jumby Bay Island are demanding you pay for two weeks over the holidays, whether or not you’re there the whole time.

The apres ski in Vail, Colorado, March 1964.
Slim Aarons/.
“It’s the No. 1 thing that gets pushback from my clients,” says Jonathan Alder of Jonathan’s Travels. “Americans do not have that flexibility of this much time off.”
Festive minimums aren’t new, but the ballooning length of required stays this year is novel. With both Christmas and New Year’s Day falling on Fridays, there’s no way to split the holidays into two blocks of seven nights, since no one wants to travel on either of those days.
The other shift is the increase in demand: There are far more would-be guests than there are rooms to house them. Hotels hold all the (key) cards.
“People are traveling more than ever,” Ganz says. “You’ve got to be willing to do what [properties] are asking…. They can do this, because the demand is there.”
There are some upsides to such uptightness. If occupancy remains consistent for such an extended period, it effectively creates a pop-up country club, says Cari Gray of Gray & Co., another Travel Master. “You get to know the staff and have your own ski guide for the whole time,” she explains. Then there’s the implicit appeal of knowing you’re only going to encounter other certified V.I.P.s.
But this isn’t enough to entice everyone. Last year, one of Jackson’s clients, who always travels with extended family, wanted to spend two weeks in the Caribbean, splitting his time between hotels. He quickly rejected paying for nights he wouldn’t use. Instead, he chartered a six-cabin yacht for the first time, spending about $1 million on the two-week charter, or roughly 20 percent more than the combined cost of several rooms across various properties.
He could flit around the Bahamas at his leisure and have the entire experience configured to his liking, from chef-made meals to daily activities. “The client said, ‘We just loved it—we’re yachters now,’ ” Jackson says. “And the properties have lost him as a guest.”