10 best Caribbean bargains this winter

Dara Continenza
View photos

Winter may be high season for the Caribbean, but that doesn't mean money-saving deals can't be found among its clear waters and sugar-soft sand. In fact, some experts believe that the best time to book airfare to the Caribbean is from New Year's to early March, when airlines are slashing prices before the big spring-break rush. So head to a warmer clime (for a lot less dime) with one of these great deals for hot spots like Jamaica, undiscovered charmers like Bonaire, and shopping paradises like St. Thomas.


Technically, the Bahamas is just outside the Caribbean Sea, but culturally and geopolitically, it's closely associated with the Greater Antilles and other Caribbean nations. It's also inexpensive this time of year, so we couldn't resist (you won't be able to, either). Time to embark to the land of duty-free shopping, megaresorts, and endless, summery sun.

Deals and Bargains: Flights to the Bahamas are incredibly cheap due to its proximity to the U.S. and frequent service from most major lines (think around $300 from Miami via Bahamasair). Add a sweet accommodations package (they're a dime a dozen this season, especially in February and March) and you'll have a budget break in no time. The famed Atlantis resort offers oodles of resort credits for travel from January 30 through March 5, including a $350 resort credit when you stay at the luxury all-suite The Cove Atlantis, plus access to The Cove's adults-only ultrapool and beach club. For a quieter kind of stay, Pink Sands Resort offers one free night with bookings of five nights or more through February 28, as well as airport transfers and daily breakfast. We recently included Pink Sands Beach on Harbour Island in our roundup of bucket-list beaches for its blush-pink sand and relaxing vibe.

View photos

Out Islands, Bahamas

The Bahamas Out Islands are perfect for true connoisseurs of island life. With few big resorts and sparse traffic, the pristine sand and sea take center stage in this collection of tiny isles, where major pastimes trend toward swimming, snorkeling, and relaxing.

Deals and Bargains: What better bargain is there than a free flight? We included the Bahamas Out Islands in our 2013 edition of 10 (Almost) Free Travel Deals for just this reason: With the purchase of a four-night air-inclusive package, MyOutIslands.com will throw in two round-trip airline tickets from Nassau—for free. Participating hotels span the islands and include luxury properties on Exuma and Eleuthera. Going one step further, Resorts World Bimini offers a private chartered seaplane from Miami with the purchase of a two-night stay (starting at a wee $389 per person).

View photos

 St. Thomas, U.S. Virgin Islands

Of the three major U.S. Virgin Islands, St. Thomas is perhaps the most budget-friendly, given the wide variety of accommodations options and activities built to entice cruisers (including prime duty-free shopping). Add in beautiful Magens Bay, one of the top beaches in the world, and you've got a complete Caribbean escape.

Deals and BargainsVisitUSVI.com is running its popular Intimate Treasures deal, which includes $100 in dining and attractions certificates and a complimentary gift bag; 14 St. Thomas hotels are participating. Frenchman's Reef & Morning Star Marriott Beach Resort has put together a number of money-saving packages, including a kid-friendly Family Island Adventure Package that includes a $200 credit toward the in-resort Adventure Center (rates from $224 per night). For cruising at bargain-basement prices, check out the seven-day sailing on Carnival's Liberty with a full-day stop in St. Thomas from just $369 per person.

Pro Tip: East Coasters can fly to the USVI for pocket change on JetBlue; a recent search turned up Monday-through-Monday flights in February and March from only $340 (Boston) and $431 (New York). (Photo by Frenchman's Reef & Morning Star Marriott Beach Resort)

View photos


The least crowded of the so-called ABC Islands (the others being Aruba and Curacao), teeny-tiny Bonaire is a diver's paradise, with one of the most abundant fish populations in the Caribbean Sea. Explore its active dive sites before settling into some quiet, inexpensive digs ashore. There are no high-rise resorts on this island, so crowds tend to be thin, prices low, and deals abundant.

Deals and BargainsPriceofTravel.com notes that Bonaire is "certainly one of the cheaper Caribbean islands for accommodations." Indeed, find seven-night stays at Bonaire's Harbour Village Beach Club from just $1,450 per person, including six single-tank dives and a full daily breakfast. A similar deal at the PADI five-star Divi Flamingo includes seven nights with unlimited shore diving from $837 per person. Even landlubbers will enjoy TripAdvisor Travelers' Choice 2013 winner Coral Paradise Resort, where vacation packages include a four-door car rental and free taxi pickup (from just $760 per person). See TourismBonaire.com's hotel guide for more options and savings.

View photos

Dominican Republic

This ever-popular destination draws tourists of every stripe, from spring breakers seeking low-cost beach thrills to families looking to make sandcastles in the sun. A wealth of all-inclusive resorts clustered around Punta Cana offer a lot of bang for your travel buck this season.

Deals and Bargains: According to Priceline, round-trip flights to the DR are unusually inexpensive this year, with flights from Chicago in the low $400s. Take advantage of cheap airfare and consider a number of budget-friendly hotels, including Barcelo Bavaro Palace Deluxe (with 30 percent off through January 31 and up to 20 percent off from February 1 onward), the Four Points by Sheraton Puntacana Village (with a la carte rates from $92 per night), and 40 percent off rack rates plus up to $400 in resort coupons at Dreams Palm Beach Punta Cana for travel through April 18.

View photos

Puerto Rico

This U.S. commonwealth has it all, from golfing to gambling and from salsa dancing to surfing. Beyond San Juan's vacation condos, the island abounds with waterfalls, colonial history, and the national rainforest of El Yunque. The best part? You don't even need a passport to get there.

Deals and Bargains: According to Priceline, in late January and early February, flights are as low as $329 from New York on JetBlue or Delta. (And right now, JetBlue Getaways is offering amazing deals on four-night packages, including airfare, accommodations, and resort credits, starting at $745 per person.) Inexpensive hotel options aren't hard to spot, either. For instance, the highly rated San Juan Marriott Resort & Stellaris Casino has a kids-eat-free deal that, at around $244 per night in March, won't drain your bank account, while the Wyndham Grand Rio Mar Beach Resort & Spa doles out a $100 food-and-beverage credit plus 25 percent discounts on sports and spa treatments for four-night stays. And a bit of Internet research will uncover even more deals; we found the cheapest rates clustered around San Juan.

View photos


The island nation of Jamaica has a number of destinations—namely Negril, Montego Bay, and Ocho Rios—that abound with bargain-priced all-inclusives come colder months. Some 3 million people visit this island, with its uniquely African heritage and a party scene fueled by world-famous rum. The best news is that an excess of hotel inventory is leading to some hot deals right now.

Deals and Bargains: Enjoy rates from $160 per night in March at Moon Dance Cliffs, a picturesque spot in Negril that's also a perennial TripAdvisor fan favorite. Sandals features up to 65 percent off when booking last-minute rates for winter, including at its original property in Montego Bay (where rooms come with butler service and multiple pools set the standard for Jamaican all-inclusives). For a true budget stay that comes with an ocean view, check into the Silver Seas Hotel, where advanced bookings for February and March start at $78 per night.

Pro Tip: Jamaica is a popular destination on Groupon Getaways; we often see as much as 45 percent off all-inclusive packages.

View photos

St. Lucia

Commonly thought of as a paradise for honeymooners and the well-heeled, St. Lucia may be surprisingly budget-friendly. Savvy travelers can find ways to swap their snow boots for bathing suits and make this a luxe yet wallet-friendly destination.

Deals and Bargains: Save up to 50 percent on winter travel at Coconut Bay Beach Resort & Spawhen booked by January 31. Splurge a little on a once-in-a-lifetime vacation at four-star Ti Kaye Resort & Spa, where winter rates have been slashed by 25 percent for travel through April 15—and some rooms come with private plunge pools. Or cruise your way through St. Lucia and Martinique on a brand-new sailing trip with adventure-travel outfitter Intrepid; starting at $1,130 per sailor, this tour works out to be about $160 per person, per day. Browse vacation packages and other specials on StLuciaNow.com.

View photos

Riviera Maya, Mexico

Activities along this stretch of Caribbean coastline are charming and varied, from wreck dives in Puerto Morelos to ziplines that thread through natural parks. Explore subterranean cenotes, climb ancient ruins, or just kick back in a beach lounger with a fruity drink, stress-free (and without breaking the bank).

Deals and Bargains: Plenty of competition in the airline market makes the Riviera Maya cheap to reach, and a surplus of resorts means staying is just as reasonable. Book by January 31 and get 40 percent off rack rates at a number of Palladium properties in the region, including the Grand Palladium Riviera Maya Resort & Spa and the adults-only The Royal Suites Yucatan by Palladium. As of press time, CheapCaribbean.com has four-night air-inclusive vacation packages at the Ocean Coral & Turquesa from just $749 per person (normally at least $1,000). Check out this up-to-date roster of deals. (Photo by Grand Palladium Riviera Maya Resort & Spa)

View photos


Its rainy season (from June to mid-November) may be the cheapest time to visit, but year-round, Belize offers great value for travelers willing to do some research. Its eastern shore is bordered by the Caribbean Sea, making this region a tropical getaway—complete with crystal-clear water, barrier reefs, and mangrove swamps just waiting to be discovered.

Deals and Bargains: Airfare to Belize isn't quite as cheap as other Caribbean destinations; however, you can find discounted accommodations in the country's laid-back beach towns. Placencia's Blue Crab Beach House, a cozy vacation rental on a private beach, offers weekly rates of just $900 and accommodate up to four people. In ritzy Ambergris Caye, Pelican Reef Villas offer 15 percent off room rates for stays through April 30, with two-bedroom pool-view rooms going for $262.65 per night. Most conveniently, the Belize dollar has a 2:1 exchange rate with the U.S. dollar, which means that prices on accommodations and goods are very reasonable. In fact, Lonely Planetnotes that "shoestring travelers can survive on BZ $60 to BZ $80 a day." (Photo by Ambergris Caye, Belize via Shutterstock)

More from Smarter Travel:

•  10 (Almost) Free Travel Deals: 2013 Edition
•  10 Caribbean Destinations You Can Afford to Visit
• Top Five Bargain Destinations for Winter 2013/2014