The 9 Caribbean Islands You Need to Visit in 2019

The Caribbean is back, baby. Recovery might still be under way, but one thing’s certain: for these nine islands, 2019 is their year.

Senior Editor, Jetsetter | @lindseytravels |

See recent posts by Lindsey Olander

Room at SIlversands in Grenada
Living room at SIlversands


Despite escaping the wrath of Irma, this Lesser Antilles isle still remained off tourists’ radars—until this year, that is, thanks to the highly anticipated debut of Silversands, the most luxurious hotel to hit Grenadan sands since Spice Island opened more than two decades ago. What to expect: 43 sleek, light-filled suites from Paris-based architects AW2 (have you heard of Amanjena?); a buzzy Thai restaurant; a spa and rum bar; and an unbeatable location on Grand Anse, the island’s best beach. As if on cue, two new direct flights from American Airlines and Air Canada are making getting there that much easier.



Anguilla’s comeback since Irma has been inspiring to watch, and 2019 is the year it can finally say it's “back in business.” Three of Anguilla's best hotels have reopened following impressive renovations, including Belmond Cap Juluca (whose $120 million revamp introduced a "disappearing spa" that melts into the landscape), Malliouhana, an Auberge Resort (now with two-tiered infinity pools and new beachfront suites), and the Four Seasons, whose Kelly Wearstler–designed interiors and cliff-side restaurants are as alluring as ever. Don’t miss a visit to Shoal Bay, a two-mile stretch some consider to be one of the best beaches in the world.

RELATED: The Best Hotels in Anguilla are So Dreamy, You'll Never Want to Leave

Bedrooom of Barbuda Belle Hotel
Restaurant at Barbuda Belle Hotel


Barbuda Belle, one of our favorite hotels in the Caribbean and the only luxury option on Barbuda, was forced to shutter in 2017 when Irma's 180-mph winds destroyed much of the property. You could say the excitement was real when the property reopened this past November, debuting two freshly built bungalows (bringing the total count to eight) along with a shiny new beach bar and grill. What’s more, Delta recently announced a new nonstop flight from JFK to Antigua's V.C. Bird airport—the gateway to this tiny sister island.

Bedroom of Mandarin Oriental Canouan
Living room at Mandarin Oriental Canouan
patio of Mandarin Oriental Canouan


The first Mandarin Oriental to “break ground” in the Caribbean took over the bones of the lavish Pink Sands Club, a 33-room all-suite retreat in the heart of St. Vincent and the Grenadines. The result is expectedly luxe—think multi-story villas, personal butlers, two fine-dining restaurants, and a spa with palapa-style treatment rooms on a hill overlooking the sea. Flashes of pink nod to the resort’s roots and you’ll find them everywhere, from the umbrellas lining the tortoise-roamed beach to the loungers by the pool. Word on the street is a Soho House and an Aman are also in the works, but if Instagram shows us anything about what’s trending right now, it’s that Canouan is already the place to be.

RELATED: The Best Luxury Hotels in the Caribbean Worth the Splurge

Le Barthélemy Hotel
Le Barthélemy Hotel
Aerial view of Le Barthélemy Hotel

St. Barts

One of the Caribbean’s most glamorous islands has finally reclaimed her throne. The palm trees are back, the beaches are beautiful again, and the island’s legendary hotels—including Cheval Blanc and Le Barthélemy—are reopen and better than ever (with Le Guanahani and Eden Rock looking to be ready by the end of the year). One notable newcomer on the scene is Villa Marie Saint-Barth, a breezy 25-room escape above Flamands Bay involving bungalows, Asian-inspired spa treatments, resident turtles, and a storied French restaurant (Francois Plantation) that pre-dates the hotel.

Aerial drone view of Caribbean resort Bavaro, Punta Cana

The Dominican Republic

Those in the mood for a sophisticated all-inclusive that hasn’t yet been overrun with spring breakers, set your sights on the Dominican Republic. Far from the crowds of Punta Cana’s main drag, the five-star Grand Reserve at Paradisus Palma Real is for couples who only settle for the best. In this case, that’s freestanding soaking tubs and private balconies with whirlpool tubs in all 288 rooms, a private beach and beach club, seven restaurants, a sumptuous spa that uses Natura Blissé products, a cigar bar, and even an on-site water park. Want to take that vaca one step further? Swim-up suites grant you direct pool access—and bragging rights.

RELATED: Jetsetter's 2019 Best of the Best Hotel Awards



Travel to Cuba is still not the easiest thing for Americans. For general travelers, your visit has to fall under the specifications of the “Support for the Cuban people” category, which dictates you stay in casas particulares (private residences) as well as patronize only locally owned restaurants and shops (i.e. not support any businesses that benefit the Cuban military). Still, interest in this once closed-off nation is stronger than ever. Whether you’re planning to stay in Havana or strike out for Trinidad or Viñales, it’s best to plan your trip with a local, who will know the businesses you can visit and book all your reservations.

See All Hotels in Cuba
Bedroom of Dorado Beach in Puerto Rico
Spa at Dorado Beach
Pool at Dorado Beach

Puerto Rico

When Puerto Rico native Lin-Manuel Miranda announced he’d be performing in a two-week run of Hamilton in San Juan this past January, Puerto Rico was put back on the map—and, for the first time in what’s seemed like years, it's all good news. Despite still experiencing the aftershocks of Hurricane Maria, the island is welcoming tourists back with open arms, currently clocking in as the fifth-most-booked spring break destination for Americans this year. Dorado Beach was the first resort to reopen, attracting big names like Uma Thurman, Neil Patrick Harris, and chef Jose Andres who rallied to show their support. San Juan, too, is thriving, and a new hotel—the very stylish, adults-only O:LV Fifty Five—marks the beginnings of a new era.


The Bahamas

We don’t know about you, but those double-header Fyre Festival docs that recently took Netflix and Hulu by storm only made us hungry for more—of the Bahamas, that is. According to the Tourism and Aviation Minister, 2018 was a banner year for tourism in the islands, and 2019 shows no signs of slowing down. Atlantis and Rosewood Baha Mar both debuted huge changes for Nassau, the islands are officially Zika-free, and a new focus is now on the lesser-visited Out Islands including Cat Island, Eleuthera, and Andros, where the 96-acre private island resort Kamalame Cay is drawing sun-seekers with its airy beachfront bungalows, stilted spa, and miles of unspoiled sands.

What to Wear in the Caribbean

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