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If you haven’t booked holiday travel yet, you’re already late
Cast a wide net
The reality is that this year, booking holiday trips in September is already too late. “Labor Day is usually the defining moment for a lot of people, when they look at the remaining options and hit the trigger,” says Rowan. “But private villas and homes in popular destinations were all gone by May or June this year. Anything with four to eight bedrooms — all gone.”
The consensus is that travelers looking now have to be flexible, either about what type of accommodation they’re booking or where they’re going. Or both.
“People who pushed deposits from 2020 to 2021 have been locked in for a year, and others planned early because they didn’t want to get stuck with nothing,” explains Tumpowsky. “For everyone else, it means you have to look more broadly than you’re accustomed to. You can’t just insist on going to Barbados or on getting a particular category of room.”
Don’t plan on island hopping, either, says Hickox. Many hotels have longer minimum stay commitments during the holidays — typically seven nights. Plus, crossing various borders exposes itineraries to greater risk of countrywide shutdowns, testing complications, and additional annoyances.
If you’re willing to think about an exotic destination such as French Polynesia, many hotels impose stricter cancellation requirements over the holidays, so a booking can only be rescheduled — not refunded — if it’s forfeited within 60 days of scheduled arrival. (Deposits may be taken as early as 90 days out.) That’s a big window during which things can change. An alternative is to seek out such exceptions as the St. Regis Bora Bora, which offers no-charge, 14-day cancellations even through festive season, when a weeklong booking in an overwater bungalow runs roughly $20,000.
And consider both classic destinations and next-great-places, say the agents. “St. Barth is going to be over the top — it’s just going to be a zoo, as crazy as it’s ever been,” predicts Tumpowsky, based on early demand. Rowan says his clients, who “are sick of Cabo at this point in the pandemic (they’ve been so many times),” are looking to less-conventional destinations in Mexico, including Oaxaca, Puerto Escondido, Todos Santos, and La Paz. Those who’ve been shut out of the best hotels in Costa Rica, he adds, are considering Colombia, Panama, and Nicaragua. The issue, he says, is that with some less-developed destinations, “there may be less inventory. Sometimes it’s just three great hotels—and guess what, they’re probably all full, too.”
Knowledge is power
Before making any deposits, familiarize yourself with the terms of the reservation. If you’re expected to pay 60% of your accommodation cost up front, are you comfortable parking that sum of money with your chosen hotel? The answer may depend on whether you’re going there to join a crew for a New Year’s party or it’s a destination you’ll be happy to return to.
Try to investigate the destination’s contingency plans, too. At this point in the pandemic, says Hickox, there are historical precedents for how destinations have handled outbreaks: Anguilla has been quick to tighten the rules, for example, whereas such places as the Dominican Republic have been reluctant to do so. “The biggest concern we have is: Are these places going to be ready?” says Tumpowsky. “What will the rules be?”
You can also look to the airlines for good clues. “St. Kitts has connectivity problems with the Northeast because the island can’t figure out a plan to handle outbreaks,” Tumpowsky says. “Airlines want to understand what it would take to close down—what demand is going to look like—so hazier forecasts make airlines less willing to drop in a daily flight from New York vs. requiring a connection in Miami.”
Get insurance
Be prepared for a medical evacuation, if you should come to need one —especially if you’re heading to an island with limited hospital beds. There’s still a pandemic raging, after all. Companies such as Covac Global sell policies that cost around $800 for a two-week trip, guaranteeing that you’ll be repatriated with no questions asked should you register positive on a COVID-19 test while on vacation.
You’ll also need a separate travel insurance policy to protect your investment. “Cancel-for-any-reason policies generally ensure that you get 75% of your deposit back,” advises Rowan. “We’re recommending it to everyone.” (This tool by SquareMouth makes it easy to comparison shop for policies.)
Or wait until the very last minute
Don’t expect last-minute deals this year; there won’t be enough open inventory for any luxury resort to justify lowering its prices. But you may find increased flexibility if you’re prepared to wait and see, particularly when it comes to those minimum-stay requirements. It’s a beneficial approach for the cash-rich and time-poor.
Position yourself to take advantage of last-minute cancellations. “People will still feel uncomfortable at the last minute, someone will get sick, and hotels won’t tell the person who tested positive for COVID to come down, anyway,” says Tumpowsky. “But in order to be first in line for cancellations,” he adds, “you need an adviser.”
The best way to leverage that advantage is to know exactly what you want. A family of five that compromised on their Christmas vacation by booking a two-bedroom suite instead of the three-bedroom villa can have their adviser monitor the accommodation they preferred for cancellations. “We’re good at being at the front of the line if there’s a very specific thing you’re after,” Tumpowsky explains.
“My best advice for someone who’s just starting to plan is that flexibility is key,” adds Hickox. “Take everything as it goes. You’ll have a good experience if you can just roll with the punches.”
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