8 Reasons Why You Should Go to the Caribbean This Winter

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.

Courtesy of JetBlue

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

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.

Related

Here’s What You Need to Know About Getting Tickets to See “Hamilton” in Puerto Rico

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.

Courtesy of Shutterstock.com

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

Courtesy of Baha Mar

The Skybar opens at the SLS Baha Mar in January.

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.

Photo by Filipe Frazao / Shutterstock.com

The obelisk at Malecón in 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

Courtesy of Small Luxury Hotels

The Gingerlily mansion villa at The Liming Bequia

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).

Courtesy of Shutterstock.com

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

Trunk Bay on St. John in the U.S. Virgin Islands

Courtesy of Cobblers Cove

The historic Great House at Cobblers Cove

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