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Caribbean palm treeYes, we’re halfway into December, which is precisely when last-minute planners from the frozen, non-Sun Belt regions start dreaming of spending the holidays on a Caribbean beach somewhere, anywhere. Conventional wisdom, says a recent New York Times article, asserts that booking now for a late December getaway is “a fool’s errand, and a rich fool at that.”

But is it? If you’re flexible on destinations and dates, is it possible to still pull off a reasonably priced getaway around Christmas and New Year’s? Or would you be better off booking now for a trip later in the winter? Seth Kugel, author of the Times article, set about researching this very question, using Google’s “Explore Flights” page to find the best airfares.

Since there’s not a comparable search tool for lodging, Kugel went to, whose ratings he says he trusts more than TripAdvisor since only allows users who have booked and paid for a hotel to review it. His minimum criteria:

1) A trip for two people, between Saturday, Dec. 21 and Sunday, Jan. 5

2) The route: New York City to a tropical beach

3) A maximum flight time of six hours, including layovers

4) Four nights in a hotel (or guesthouse or hostel with private rooms) with a minimum rating of 7.5 (in the midrange of the site’s “Good” level)

His basic questions: What, if anything, was still available? Are certain travel days better than others? How much would you save if you booked a similar trip now for later in the winter?

Kugel’s search included 12 classically beach-y locales in and around the Caribbean, including budget destinations like Montego Bay, Jamaica; Punta Cana, Dominican Republic; and Cancún, Mexico; slightly more upscale spots like San Juan, P.R. and Key West, FL; as well as Panama. Here’s what he found:


The cheapest round-trip flights he could find are after the pre-Christmas weekend rush to get out of town but before Christmas Day (Monday, Dec. 23 and Tuesday, Christmas Eve). Traveling on the cheapest days meant a 30-50% savings over traveling on the most expensive, which were mostly for trips that included New Year’s.

Surprisingly, some of the cheaper flights were not much more expensive than ones to the same destinations more than two months out for midwinter break, the week starting Feb. 15. Sometimes, in fact, it was cheaper: You could get to Nassau in the Bahamas over Christmas for $422, but the lowest flight over February break was $476.

Kugel advises that anyone willing to travel during non-holiday or non-break stretches of January and February could save quite a bit. Some of the biggest differences: The best rate over Christmas for St. Thomas is $649 but that drops to $335 on some other winter dates; for Aruba, $622 vs. $396; Cancún is $685 versus $365; and for Barbados, a whopping $913 vs. $486.


Unlike flights, hotel prices followed no obvious pattern and tended to complicate things, Kugel writes. A $649 flight to St. Thomas makes Dec. 23 look like the best day to leave for the Virgin Islands, except the cheapest available hotel on with a rating over 7.5 for those dates was over $600 a night. Yikes!

On the bright side, sometimes cheaper flight days in fact match cheaper hotel days. Kugel was able to pair a $685 flight to Cancún on Dec. 24 with a $66-a-night room at the Hotel Suites Gaby. However, if you want to fly on Dec. 26 ($1,203), the cheapest available hotel was over $600 a night. But if you plan ahead and book now for a February vacation week, you can save 17-64% percent over holiday-time lows (sometimes even more if you’re open to other dates).

Best Deals

The overall cheapest four-night getaway Kugel found was to San Juan, from Dec. 21 to 25, traveling nonstop on JetBlue for $447 and staying for $78 a night at the Casa Del Caribe Bed & Breakfast. Grand total for two: $1,206. A Montego Bay combo was second at $1,558, and St. Maarten third at $1,836.

Kugel also notes that while it may not be as tranquil nor toasty a getaway, you can still get down to Miami Beach over the holidays more cheaply than any place mentioned above. There were plenty of flights for under $500 (compared with $250 or so later in winter). And the average high temperature? Mid-70s — not bad for the price tag.

Happy holiday travels!

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