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.