Laura Magruder for The New York Times
Catching a wave in San Juan, P.R.
We're into December, when last-minute planners from New York and other scarf-wearing regions start dreaming of spending Christmas break on a Caribbean beach somewhere, anywhere. Or, to put it more accurately, dream of having had the foresight to plan such a trip in August, when prices — both flights and hotel rooms — were still reasonable. Conventional wisdom has it that booking now for a late December getaway is a fool's errand, and a rich fool at that.
But is it? Could someone who was flexible on destinations and dates still pull off a reasonably priced getaway around Christmas and New Year's? Or would they be better off reserving now for later in the winter?
I decided to look into these matters with some good old-fashioned research. Well, not too old-fashioned: I used Google's "Explore Flights" page, an amazing site that lets you set a few criteria — what region you want to visit, how many days you want to go for, acceptable departure times and flight lengths — and then spits out a list of destinations with a day-by-day bar graph of the best airfares. (I found that they were occasionally inaccurate, especially with JetBlue flights, but the errors were within a $50 margin and always overestimated the cost.)
Unfortunately, no such tool works the same magic for lodging. So I decided I'd do standard searches on Booking.com, whose ratings I trust more than TripAdvisor since they claim to allow only users who have booked and paid for the hotel to review it. Here were my minimum criteria:
1) A trip, for two people, between Saturday, Dec. 21, and Sunday, Jan. 5 (which I'll call "Christmas break").
2) The route: New York City to a tropical beach
3) A maximum flight time of six hours, including layovers
4) And four nights in a hotel (or guesthouse or hostel with private rooms) with a minimum Booking.com rating of 7.5 (in the midrange of the site's "Good" level)
The idea was not to find and recommend specific itineraries. Instead I wanted to answer some questions: What, if anything, was still available? Are certain travel days better than others? And how would you save if you booked a similar trip now for later in the winter?
So on Tuesday afternoon and Wednesday morning of this week I searched 12 classically beachy locales in and around the Caribbean, including budget destinations like Montego Bay, Jamaica; Punta Cana, Dominican Republic; and CancĂșn, Mexico; slightly more upscale spots like San Juan, P.R., and Key West, Fla., ; as well as Panama, as a wild card. It was exhausting, but hardly exhaustive — I may not have found all the best deals, nor was my 7.5 rating requirement the way I would typically decide on lodging. But enough caveats. Here are my findings.
Flights
The cheapest round-trip flights are after pre-Christmas weekend rush to get out of town but before Christmas Day — in other words, Monday, Dec. 23, and Tuesday, Christmas Eve. (The only exceptions I found: San Juan, where leaving Saturday, Dec. 21, was the cheapest available, at $447, and Antigua, where traveling on Christmas Day was cheapest, at $880.) Traveling on the cheapest days meant a 30 to 50 percent savings over traveling on the most expensive, which were mostly for trips that included New Year's.
That was not a shock, although I had expected traveling on Christmas Day would have been cheapest in more than just one instance. What surprised me more was that some of those 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.
Still, anyone willing to travel during non-holiday or non-break stretches of January and February could save quite a bit. A few examples of the biggest differences: The best rate over Christmas for St. Thomas is $649, but that dips to $335 on some other winter dates; for Aruba, it's $622 versus $396; CancĂșn, $685 versus $365; and for Barbados, a whopping $913 versus $486. (Get your Bajan food in Brooklyn this year.)
Hotels
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