The Best Time to Visit the Caribbean (and the Worst)

PHOTO: The Cove Eleuthera, Bahamas
Oyster.com

The best time to visit the Caribbean is pretty obvious. Just think about when you most want to go on an island retreat...over the holidays, right? When the weather stateside is largely still dreary and cold. If we're talking about the best time to visit the Caribbean in regard to temperatures and convenience, smack over the major holidays (Thanksgiving, Christmas, and Easter -- the latter coinciding with spring break) is arguably it. But if we're discussing finding the most bang for your buck, it's a different story.

See, the nearly 30 million Americans (calculated by the U.S. Office of Travel & Tourism Industries) who travel overseas annually seek a holiday beach getaway, just like you. Therefore, this is the time when flight and hotel prices skyrocket.

But if your heart is set on a Caribbean vacation in the next several months, we do know a few hacks that will help you stretch your dollar and still come home with an enviable tan and some cash in your waterlogged wallet.

PHOTO: Saving on Flights
Oyster.com

It seems no flights these days are cheap -- except maybe those jumping from one European city to the next in rickety planes where peanuts, even to purchase, aren't an option...

And we advise against those.

However, there are dates and times of day for flights that are noticeably cheaper than others, even during the ever-expensive holiday season.

Here are some guidelines to help you avoid insanely expensive ticket prices if you're planning a Caribbean getaway in the next six months:

  • Book your flight about seven weeks prior to your departure date. This will generally get you the best price, according to a study by CheapAir.com.
  • Flights taking off early in the morning or late at night are often the least expensive.
  • FareCompare.com. has found that Tuesdays, Wednesdays, and Saturdays are the cheapest days of the week to fly.
  • Your airfare will almost always be cheaper if you allow for a layover (ugh). But, in our opinion, you've really got to be in the holiday spirit to stay cheery when a connection is missed due to a canceled flight!
PHOTO: Waves Barbados
Oyster.com

Hotels...now we're really in our area of expertise.

Based on the booking and travel patterns of our Oyster.com users, as well as the fluctuating rates of the hundreds of Caribbean properties on our site, we've found some noteworthy statistics that will help you get the most bang for your buck during your next Caribbean hotel stay:

  • While travelers generally book hotel rooms between 40 and 80 days in advance, this really doesn't make much of a difference in price. Instead, it's the dates you plan on vacationing that matter, so read the fine print before you think booking your room three months in advance is beneficial; depending on the hotel's cancellation policy, it may end up doing more harm than good.
  • Not surprisingly, prices peak over the weeks of Thanksgiving, Christmas, and Easter. Research shows that you'll often find the best hotel deal if you book a room for one of the first two weeks of December.
  • Hotel rates also dip in the first full week after New Year's, and again in mid-April, when the weather stateside starts to warm up.
PHOTO: This infographic shows details on average room rates in the Caribbean for various dates between November 1, 2015 and May 31, 2016.
Oyster.com

Take a look at this Infogram to get more details on average room rates in the Caribbean for various dates between November 1, 2015 and May 31, 2016.

So Now That We've Laid Out All the Facts, Here's the Scoop:

  • The best time for stretching your dollar over a week-long Caribbean getaway this holiday season is from Saturday, December 5 to Saturday, December 12. And be sure to book an early morning flight!
  • The worst time to visit the Caribbean if you're looking for a solid bang for your buck is from Monday, December 21 to Monday, December 28. And don't skimp on a thing -- book a direct, midday flight to really up the price.

Now We Want to Hear from You: How far in advance do you book? Do you travel to the Caribbean during the holidays? How much time do you spend researching deals? Let us know in the comments!
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