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If you haven’t booked holiday travel yet, you’re already late
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If you haven’t booked holiday travel yet, you’re already late

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Christmas is less than 100 days away. And if 2021 hasn’t quite been the year most people hoped for, with no end of the pandemic in sight yet, it seems Americans are ready to bank on a big consolation prize: an epic holiday vacation.

“All day long, we’re booking Caribbean and Mexico, Caribbean and Mexico,” says Barkley Hickox, partner at the luxury travel advisory Local Foreigner, about the current flood of year-end requests. “The demand is huge,” echoes Paul Tumpowsky, founder of digital travel agency Skylark.

It’s also full of anomalies.

This year, Americans feel hemmed into fewer options than usual. Skiing in Europe — or visiting holiday markets there — feels too risky, says Tumpowsky, adding that clients are sick of having their trips canceled and rescheduled. Even if domestic travel is the only surefire bet, there’s no guarantee of December snowfall in the ski resorts or of warm-enough weather for swimming anywhere north of Florida.

“One of my board members — who in the past has made a holiday tradition of, say, spending $250,000 for a trip to Vietnam — this year, his plan is Miami,” Tumpowsky says.

“When people ask us about a safe bet for holiday travel,” says Hickox, “they’re not asking about COVID-19 policies.” Instead, she says, a “safe bet” translates to reliability: knowing the weather will be good and that border policies are unlikely to change. Hence, Mexico and the Caribbean, whose economies rely heavily on the winter tourism season.

Throughout the region, resorts are commanding astronomical prices for what’s left of their limited inventory. At the Mandarin Oriental Canouan in St. Vincent and the Grenadines, rooms over the Christmas-to-New Year’s period are running at $4,050 a night and up— more than four times the rack rates in November. A garden-view, entry level room at the Four Seasons Ocean Club in Nassau, the Bahamas, which usually fetches around $1,000 per night, is commanding $2,500 over the holiday period. (The cost doubles if you want views of the water). A relative deal, the Ritz Carlton Grand Cayman, on the island’s Seven Mile beach, is asking $1,719 for its somewhat old-school rooms. If you were to stay just one week earlier, you’d save $700 per night.

With few rooms remaining at all of them, it’s clear that people are willing to pony up, even if it’s for lack of better options.

“Costa Rica is as far south as you can realistically go,” says Tumpowsky, citing a mix of weather and border restrictions. “If you can convince yourself to go somewhere domestic, like Sea Island [in Georgia] or Palmetto Bluff [in South Carolina], it’s going to be stupid expensive—and cold.”

Leigh Rowan, whose consultancy Savanti Travel serves ultra-high-net-worth travelers in the Bay Area, adds one more limitation: “Hawaii is already full,” he says. “I mean full, full, full, full, full.”

For travelers hell bent on giving the festive season its due, that means a lot of considerations that wouldn’t apply in a “normal” year. Here’s how to navigate holiday travel planning if you—like so many others—are still unsure as to what travel will look like in three months.

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