8 Reasons Why You Should Go to the Caribbean This Winter

After a catastrophic 2017 hurricane season, the Caribbean is back in business and ready to welcome travelers.

8 Reasons Why You Should Go to the Caribbean This Winter

Picture yourself in this hammock on Grand Cayman’s famed Seven Mile Beach.

Courtesy of Shutterstock.com

It’s been more than a year since Hurricanes Irma and Maria cut across the Caribbean, leaving varying degrees of devastation in their wake. While some islands recovered quickly or completely avoided the storms, others places are finally back in business for high season this winter after a long rebuilding process.

From iconic hotel reopenings in places hit hard by the storms to annual food festivals and brand-new flight routes to harder-to-access islands, here are the eight reasons you’ll want to book a warm-weather getaway to the Caribbean this winter.

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Lin-Manuel Miranda arrives in Puerto Rico on a JetBlue flight in advance of his three week run of “Hamilton.”

Courtesy of JetBlue

Watch Lin-Manuel Miranda reprise his role in Hamilton
San Juan, Puerto Rico From January 11 to 27, 2019, Lin-Manuel Miranda is bringing his Broadway musical Hamilton to San Juan to help raise money for his Flamboyan Arts Fund, which supports rebuilding Puerto Rico’s art community after the devastating effects of Hurricane Maria. The regularly priced tickets sold out almost immediately, but there are still $5,000 VIP tickets available to several performances.


A majority of San Juan’s hotels are open and ready to welcome guests in town for the show, including the El San Juan Hotel and Dorado Beach, a Ritz-Carlton Reserve, which both reopened in late 2018 after extensive restorations. The iconic Condado Vanderbilt Hotel, which managed to stay open during its hurricane restoration work, celebrates its 100th anniversary in 2019, too.

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In addition to the annual Cayman Cookout, the first KAABOO festival will take place on Grand Cayman’s Seven Mile Beach.

Courtesy of Shutterstock.com

Eat at the Cayman Cookout with Eric Ripert and José Andrés

Grand Cayman, Cayman Islands

Chef Eric Ripert is hosting the 11th annual Cayman Cookout at the Ritz Carlton, Grand Cayman over the weekend of January 16 to 19, 2019, with other big-name chefs like Emeril Lagasse and José Andrés (a winner of a 2018 AFAR Travel Vanguard award).

If music and comedy are more of your thing, you can pick up tickets to the first KAABOO Cayman festival to see the likes of Blondie and David Spade perform on February 15 and 16 on Seven Mile Beach.

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The Skybar opens at the SLS Baha Mar in January.

Courtesy of Baha Mar

Drink a cocktail at the first rooftop lounge in the Bahamas
Nassau, Bahamas In addition to the Rosewood Baha Mar, which opened in June 2018, this winter is full of other firsts for the 2,300-room resort that also includes a Grand Hyatt and an SLS hotel. In January 2019, the Bahamas will get its first rooftop lounge when Skybar opens on top of the SLS Baha Mar. Before watching the sunset with a craft cocktail in hand from 20 floors above the Caribbean Sea, you can also order a burger from Umami Burger’s new beachfront Airstream trailer location that just opened at the resort in December 2018.

To encourage people to come to the Bahamas, Baha Mar is also offering an “Embrace Your Winter Blues” deal at all three properties. From now until February 15, if you book five nights for stays between January 6 and April 30, 2019, you’ll receive one night free.

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The obelisk at Malecón in Santo Domingo, Dominican Republic.

Photo by Filipe Frazao / Shutterstock.com

Celebrate the 175th anniversary of the Dominican Republic’s independence
Santo Domingo, Dominican Republic For the Dominican Republic, 2019 is a big year. A 169-room Four Seasons is in the works to open at the new Tropicalia resort near the town of Miches on the northern coast of the island. But more importantly, the nation is celebrating the 175th anniversary of its independence from Haiti this winter.

Carnival celebrations typically happen around the Dominican Republic for the entire month of February, but the main military parade takes place in the capital of Santo Domingo’s waterfront promenade, the Malecón, on Independence Day, February 27.

Plan Your Trip With AFAR’s Brand-New Guide to the Dominican Republic

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The Gingerlily mansion villa at The Liming Bequia

Courtesy of Small Luxury Hotels

Check in to The Liming Bequia
Bequia, St. Vincent and the Grenadines On November 1, 2018, The Liming Bequia opened on the second largest island in the country (pronounced Bek-way), south of the main island of St. Vincent. A member of Small Luxury Hotels of the World, this 13-villa property focuses on privacy; it includes the Gingerlily, a five-bedroom mansion beach house. Most villas have their own private infinity pools or hot tubs, but guests staying at the Gingerlily will also have private gardens and a kitchen for cooking to make their stay feel even more like home (if your home was just steps from the beach).

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If you live in the Midwest or South, getting to Aruba—and its famous pink flamingos—will be much easier this winter.

Courtesy of Shutterstock.com

Fly to Aruba with fewer connections

Orangestad, Aruba

The tiny southern Caribbean island of Aruba, just off the coast of Venezuela, has been easily accessible from East Coast cities like Miami, Charlotte, and Philadelphia for years. But this winter, the middle of the United States is finally getting its due. On December 22, 2018, American Airlines is launching nonstop service from Dallas/Fort Worth International Airport and Chicago O’Hare Airport, making it easier than ever to experience Aruba’s white sand beaches, animal sanctuaries, and beautiful national park from the Midwest and Texas.
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Trunk Bay on St. John in the U.S. Virgin Islands

Courtesy of Shutterstock.com

Help with hurricane recovery on the U.S. Virgin Islands

St. Croix, St. Thomas, and St. John

The U.S. Virgin Islands were some of the hardest hit by the hurricanes and are still recovering. That doesn’t mean you can’t go this winter. Although only half of lodgings on St. Croix, St. Thomas, and St. John have reopened, all of the beaches are back and ready to visit. To find out which hotels are welcoming guests this winter, check out the list the tourism board updates online (which includes The Fred, the first new hotel in St. Croix in 30 years; it opened in April 2018).

To help continue the restoration work during your trip, you can also participate in Purpose in Paradise, a program the tourism board started to help connect visitors with volunteer projects like beach cleanups in Virgin Islands National Park, coral reforestation on St. Croix, and home construction projects for local residents on St. John.

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The historic Great House at Cobblers Cove

Courtesy of Cobblers Cove

See the newly renovated Cobblers Cove in Barbados
Speightstown, Barbados Even though Barbados escaped the hurricanes of 2017 relatively untouched, the more than 50-year-old Cobblers Cove hotel on the west coast of the island recently completed a three-year renovation. One of only four Relais & Châteaux hotels in the Caribbean, the 40-suite property now has all new flooring, furniture, and, most importantly, bigger bathrooms. But fans of Cobblers Cove will be delighted to find that the iconic spot hasn’t changed the signature pink and white color palette of its turreted main building.

>> Next: AFAR’s 25 Places to Go in 2019

Lyndsey Matthews is the senior commerce editor at AFAR who covers travel gear, packing advice, and points and loyalty.