[Editors Update] While these prices are from 2013, they'll give you a good sense of how much you can save during the season. More importantly, our risk factor assessments can help you determine whether the deals are worth the gamble.
Nine months out of the year, Caribbean islands are a postcard-ready panorama of blue skies, swaying palm trees, and cocktail-sipping, hammock-lounging bliss. But from September to November (as in, right now), they are associated with another thing: hurricanes. As we speak, reports are showing that the season's first tropical storms are already forming.
But for those willing to roll the dice, hurricane season can also yield up some incredible bargains. Flights, cruises, and hotels often go for a fraction of their peak season rates, at a time when most travelers are too spooked by the thought of having their trip washed, blown, or flooded down the drain.
And if you're worried about showing up to a ghost town, rest assured: of the 25 million tourists who visited the Caribbean in 2012, roughly a fifth of them were brave enough to travel between September and November, the peak of hurricane season.
To give you a head start, we logged onto Expedia and CheapCaribbean and chose some hotel-and-flight packages for a range of dates in late October and mid-November. All packages are priced per-person, based on double occupancy, with flights from Miami. Other departure cities are usually available for more.
Clearly, none of the following destinations can provide guarantees on anything weather-related (otherwise they wouldn't be offering the deals in the first place!). But with prices this low, you can afford to have your trip cancelled and still have extra cash lying around to re-book the whole thing from scratch. Now, get out those bathing suits!
Punta Cana, Dominican Republic
The win: The Dominican Republic's sunny east coast resort spot has been on our mind all summer, and now is the perfect time to go. The all-inclusive IFA Villas Bavaro, which offers 262 villas among 23 bungalows, all with private garden areas and easy access to Bavaro Beach, is available for a three-night package, airfare included, for just $763. Meanwhile, if you need something a little more upscale, the luxury all-inclusive Dreams La Romana, all of whose rooms have balconies, has a three-night package from $699.
The gamble: Medium. In the past ten years, one hurricane (2004) and three tropical storms (2003; twice in 2007) have blown through the Dominican Republic with severe consequences to both the eastern and western coasts.
San Juan, Puerto Rico
The win: Puerto Rico is a long-running favorite when it comes to cheap beach getaways, but in hurricane season, certain deals can be too hard to pass up. Like? Three nights at the stunning 4-star San Juan Marriott Resort & Stellaris Casino – a hotel perched right on enchanting Condado Beach – for just $474 for three nights, including airfare. Alternatively, those looking to spend time in San Juan proper will pay just $484 for a round-trip flight plus three nights at the classic Sheraton Old San Juan Hotel & Casino, whose chic rooftop pool is one of the hotel's top attractions.
The gamble: Low/medium. Though plenty of storms have passed relatively close to Puerto Rico, only Hurricane George in 1998 caused damage to the interior of the island, though in 2011, the island sustained extensive flooding from both Hurricane Irene and Tropical Storm Emily.
Riviera Maya, Mexico
The win: Mexico spans a wide area, with plenty of interesting cities, unique adventure spots, and miles upon miles of empty white sandy beaches. But seasoned travelers know Riviera Maya is one of the country's true gems, and getting there is a cinch: the Catalonia Riviera Maya Resort and Spa, an all-inclusive resort south of Playa del Carmen with a private beach and balconies in all the rooms, costs only $494 per person, including airfare. Twenty-five miles north, the lush Fairmont Mayakoba offers lush tropical mangroves, infinity pools, and a spa for just $642 for three nights, including airfare (not bad at all, considering the same room during peak season goes for almost $400 per night).
The gamble: Medium. Jutting out into the Caribbean Sea across from Cuba, Cancun is most vulnerable to northwest-headed hurricanes and tropical storms than other parts of Mexico, and in 2011 it was hit by Category 3-level Hurricane Rina.
Montego Bay, Jamaica
The win: Holiday Inn probably isn't where you'd normally turn to for some proper R&R, but that's because you haven't been to Jamaica's Holiday Inn Sunspree Montego Bay. The 518-room, all-inclusive hotel sticks you right in front of Montego Bay, which you'll likely have all to yourself, as crowds in October and November tend to dwindle. The price? $545 for a three-night getaway, including airfare. And if the traditional resort experience doesn't appeal, then how about a stay at a upscale 400-acre estate just a few miles down the road? Half Moon's exquisite landscaped gardens, two-mile long beach, and old-world rooms with four-poster beds start at just $792 for the same period, including airfare.
The gamble: Low/medium. Though Hurricane Sandy passed within 50 miles of Montego Bay in 2012, the last hurricane to hit the area full-on was 2004's Hurricane Ivan, which brought 155mph winds and moderate damage.
Nassau and Paradise Island, Bahamas
The win: Beach-loving travelers are rarely short on incentives to visit the Bahamas – though we're feeling an exceptionally strong pull right now towards places like Atlantis Coral Towers, the mid-range island-themed section of the sprawling beachfront resort. A water park, 11 pools, three beaches, a movie theater, casino, and, oh, about a gazillion restaurants will be yours for the taking during the traditionally-quieter fall season: book three nights in a terrace room, including airfare, for $675 – alternatively, for just $40 more per night, you can upgrade to the Royal Towers.
The gamble: Medium. In 2007, Tropical Storm Noel passed straight through Paradise Island, and was upgraded to a Category 1 Hurricane; however, despite being on the direct route for hurricanes that hit mainland U.S., only a handful of such storms have hit Nassau's northeastern coast in the last 100 years.
For a good resource on hurricane history by region, visit HurricaneCity.