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5 Great Getaways in the Caribbean 

Expanded direct flights, new resorts and exciting amenities make these five islands even more alluring this winter

a kayak on the beach in the cayman islands in the caribbean

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Cayman Islands

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’Tis the season to visit the Caribbean, where balmy temps, curvaceous coves and tropical cocktails offer the perfect remedy for the winter blues. This year, there are even more reasons to chase the sun to your favorite island destinations. Spontaneous getaways are back on the table since most Caribbean countries have removed advance travel applications and pandemic-related travel restrictions. Combine that with new nonstop flights from several U.S. gateways and resorts making their debut across the region, and travelers have plenty of reasons to plan an island getaway. Of course, the cost of a getaway depends on which property and how long you stay, but rates range from about $300 a night (at the Hampton by Hilton Grand Cayman Seven Mile Beach) to more than $1,250 a night (at Quinn in Anguilla).

a boat in prickly pear anguilla in the caribbean

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Anguilla 

In the past, visitors had to fly to the island of St. Maarten, then hop a ferry or a puddle jumper to get to Anguilla, the tiny island beloved for its 33 pristine beaches, beautiful resorts and relaxed beach bars. But in November, American Airlines is adding eight nonstop 3½-hour flights a week from Miami, so travelers can have their toes in the sand by lunchtime.

Two hotels join the island’s lineup this winter: On secluded Long Bay, Quinn is an intimate hideaway boasting three suites that enjoy access to the amenities of the neighboring villa, Quintessence Hotel. Among them: an infinity pool, spa and a wine cellar. Also, the former CuisinArt Golf Resort & Spa changed hands last year and is now Aurora Anguilla Resort & Golf Club. The 178 suites and villas have sweeping views of Rendezvous Bay; seven restaurants feature ingredients grown in the resort’s hydroponic gardens; and for golf, the Greg Norman-designed 18-hole championship course and nine-hole short course are refreshed and ready for play.


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sea stars under the waves on little cayman island in the caribbean

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Cayman Islands

This three-island destination (Grand Cayman, Cayman Brac and Little Cayman) was the last in the Caribbean to reopen to tourists at the end of last year. So for visitors returning, hotels and attractions that opened in early 2020 will effectively be new. 

One standout newcomer is the Hampton by Hilton Grand Cayman Seven Mile Beach, a beachy-chic retreat steps from the sand. Rooms are a study in casual style, with neutral colors and mid-century modern furniture (a hot breakfast is included in the rate). Popular with Caymanians as well as guests is the hotel’s new restaurant, Ms. Piper’s Kitchen + Garden. Conceptualized as the home of fictional Ms. Piper, an adventuress who arrived on the island in the 1970s, it’s a charming indoor/outdoor spot that serves lunch and dinner in a poolside garden embellished with pink-striped parasols. 

To get here, Cayman Airways will offer nonstop flights between Los Angeles and Grand Cayman in November as the only direct service from the West Coast to the Caribbean.

trafalgar falls in dominica in the caribbean

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Dominica

This eastern Caribbean country is known as “Nature Island,” and given its lush tropical landscape, 365 rivers and 12 waterfalls, the title isn’t mere hype. Last year, American Airlines launched the first nonstop flights from the U.S., which depart daily from Miami and take just 3½ hours. 

For a sustainable stay, Coulibri Ridge opened in October. The eco-resort is an off-the-grid oasis on the hillside above the village of Soufrière that’s powered solely by solar energy, wind turbines and a rainwater-sourced irrigation system. Sustainability requires very few sacrifices here: Coulibri’s 14 studios, lofts and penthouses all feature kitchens and terraces with views of neighboring Martinique, and some even boast private pools and garden showers. There are two restaurants, a yoga pavilion and complimentary high-speed Wi-Fi is available throughout. 

Also new around the island: a kayaking route called the Waitukubuli Sea Trail that runs between Dominica’s northern and southern tips, giving paddlers a close-up view of marine life (watch for turtles and dolphins) as well as access to hidden beaches.

harbor ocho rios jamaica in the caribbean

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Jamaica

Jamaica has bounced back from the pandemic slump, rolling out the red carpet for more than 5 million sun seekers since it reopened for travel in the summer of 2020. The Caribbean’s largest English-speaking island — home of rum, reggae and the world’s fastest woman, Shelly-Ann Fraser-Pryce — will also welcome travelers from Chicago Midway, St. Louis and Denver airports this season on new Frontier Airlines flights to Montego Bay. 

In Ocho Rios, near the island’s famous 180-foot-high cascades at Dunn’s River Falls, Couples Sans Souci resort has been renovated and offers a new restaurant, coffee bar, spa and refreshed rooms. Planning ahead? The Sandals Dunn’s River resort is set to open in May 2023 with seven pools, nine bars and a dozen restaurants about a 30-minute drive from Sans Souci.

a view of the pitons in saint lucia in the caribbean

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St. Lucia

Known for its iconic volcanic peaks — the Pitons — this lush southern Caribbean island has a dreamy tropical landscape reminiscent of the South Pacific, but it’s only about a 4½-hour flight from New York City. This winter, look for an increase in nonstop service from New York, Boston, Philadelphia, Chicago, Miami, Atlanta, Charlotte and Dallas on American, Delta, JetBlue and United. 

Making a December debut, the all-inclusive Zoetry Marigot Bay will have 124 suites (some with private plunge pools) and a “rum cave” for tastings. It’s fitting, perhaps, that in the only country in the world named after a woman, the Landings Resort and Spa in Rodney Bay is the first in the region devoted exclusively to women’s wellness, including a program of spa treatment that launched this summer to soothe everything from menstrual pain to postpartum challenges and menopause. Nearby, the new eight-room, wellness-focused hotel Sol Sanctum offers an intimate, alcohol-free escape with yoga, tai chi and meditation classes.

Sarah Greaves-Gabbadon is a Miami-based freelance writer and editor who specializes in coverage of the Caribbean. She has appeared on numerous television outlets, and her work has been featured in National Geographic and The Washington Post. Her website is JetSetSarah.com.

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