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The reality is that booking holiday travel in September already this year is too late. “Labor Day is usually the crucial moment for many people as they look at the remaining opportunities and hit the trigger,” Rowan says. “But private villas and homes in popular destinations were all gone in May or June this year. All with four to eight bedrooms – all away. ”

The consensus is that travelers applying now need to be flexible, either about the type of accommodation they book or where they are going. Or both.

“People who pushed deposits from 2020 to 2021 have been locked up for a year, and others planned early because they didn’t want to be stuck with nothing,” Tumpowsky explains. “For everyone else, this means that you have to look wider than you are used to. You can not just insist on going to Barbados or getting a certain category of premises. ”

Also, do not plan island hopping, Hickox says. Many hotels have longer minimum stays during the holidays – typically seven nights. Plus crossing different borders exposes travel plans to greater risk of nationwide shutdowns, testing of complications and additional nuisances.

If you are willing to think of an exotic destination like French Polynesia, many hotels have stricter cancellation requirements during the holidays, so a reservation can only be rescheduled – not refunded – if it is lost within 60 days of scheduled arrival. (Deposits can be taken as early as 90 days out.) It is a large window where things can change. An alternative is to seek out such exceptions as St. Regis Bora Bora, which offers free, 14-day cancellations even through Christmas, when a weekly reservation in a bungalow over water runs around $ 20,000.

And consider both classic destinations and next big places, agents say. “St. Barth is going to be at the top – it’s just going to be a zoo, as crazy as it’s ever been, ”Tumpowsky predicts, 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 for less conventional destinations in Mexico, including Oaxaca, Puerto Escondido, Todos Santos and La Paz. Those who have been shut out of the best hotels in Costa Rica, he adds, are considering Colombia, Panama and Nicaragua. The problem, he says, is that with some less developed destinations, “there may be less inventory. Sometimes it’s just three good hotels – and guess what, they’s probably all full too. ”

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