Best Spends

This Travel Site Sends You to a Mystery Caribbean Resort -- for 75% Off

Grand Velas Resort, Riviera Maya, Mexico
Grand Velas Resort, Riviera Maya, Mexico | Courtesy Velas Resports
Grand Velas Resort, Riviera Maya, Mexico | Courtesy Velas Resports

The sandy white beaches of the Caribbean might be as close to heaven as we get in the Western Hemisphere, but the cost of getting to -- and staying on -- those islands can make the whole thing completely prohibitive.

Well, not always. Let us introduce you to CheapCaribbean, which, if you're willing to show a little blind faith, will send you to a luxury resort in the Caribbean for up to 75% off what you'd usually pay. For those who got a math waiver on the SAT, that means vacations that might typically cost $2,000 can be yours for as little as $500. It's called Deal of Fortune (no word if Merv Griffin has sued) and it's how you can afford to take the tropical vacation of your dreams.

Cheap Caribbean Mystery deal of fortune
Screencap courtesy of Cheap Caribbean

How it works

Unlike Pack Up + Go, which sends you anywhere it damn well feels like for the weekend, Deal of Fortune lets you pick which island and destination city you want to visit from a constantly updated list of potential destinations on its home page, and then sends you to a mystery resort in that place. Each destination has a range of travel dates (typically two to four months) and a class of resort you'll be staying at (typically 3.5 to five "suns," similar to the slightly ambiguous star system). Some are all-inclusive, some are not. Some include meals, some don't. And all include airfare. But CheapCaribbean tells you all this info upfront, so you know what you're in for.

You then select your travel dates (including specific flights), choose some optional extras like ground transfers and activities, and book the trip. A week before you leave, CheapCaribbean reveals the exact resort you'll be calling home for the next few days, and you get a trip at 50% -- or more -- off the price you'd otherwise pay.

But these deals are only good during off-season, right?

You pick your own travel dates, and can sometimes book up to six months in advance, so you can get these deals any time. You can literally book the day before if you want, it just depends HOW impulsive you want to be. Of course, just like with full-priced travel, you'll find better deals and lower prices during slower seasons. But that doesn't mean you won't still find 50-75% off discounts during, say, spring break or Christmas.

OK, so what's the catch? And how does it get these discounts?

The catch is you pay before you know which resort you'll be staying at. The resort description is incredibly vague, offering up such insightful details as "restaurants" and "swimming pool." But it will let you know if it's adults-only, or kid-friendly, so you don't get stuck at a pool with a bunch of screaming 8-year-olds/25-year olds. Beyond that you just have to put your faith in a company that's been doing Caribbean travel for over 15 years.

That experience is why CheapCaribbean can find deals other sites simply cannot. It negotiates deals with travel partners it's had for years, gets volume discounts for its reservations, and passes the savings along.

But the flights have to be expensive, right? It's the Caribbean.

Anyone who's been to the Caribbean knows the joy of shelling out more money to fly an hour and a half than you would to fly to Europe, but Deal of Fortune mitigates a lot of that cost too.

CheapCaribbean runs charter flights from most major US airports to these destinations, and those flights are a big part of why the Deal of Fortune prices are so low. Now, that's not the case from everywhere, and you may still find that a ticket to Aruba from your hometown puts this out of your price range. But before you say, "I live in Seattle; this is going to cost more than my student loans," take a look at what's available. You might just be surprised.

So that fruity drink on that white sandy beach isn't quite so far off as you might have thought. For less than the price of a few days in one of America's best weekend getaway cities, you can send yourself to an all-inclusive resort in the tropics. And if you don't need to plan out every last detail of your trip, you can be listening to "Single Ladies" on a steel drum as soon as Friday night.

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Matt Meltzer is a staff writer with Thrillist. Plenty of Caribbean pictures to be had on his Instagram: @meltrez1.
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