5 Great Getaways in the Caribbean for a Winter Escape (2024)

It is the season in theCaribbean, where balmy temps, curvaceous coves and tropical co*cktails offer the perfect remedy for the winter blues. This year, there are even more reasons to chase the sun to your favorite island destinations. New nonstop flights from several U.S. gateways, and new and renovated resorts making their debut across the region offer even more justification (as if you need it!) 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 $400 a night (at the Hampton by Hilton Grand Cayman Seven Mile Beach) to more than $1,000 a night (at Six Senses La Sagesse in Grenada).​

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Anguilla

Travelers can enjoy boating and other activities when visiting the island of Anguilla.

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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 American Airlines now offers daily nonstop flights fromMiami, so travelers can have their toes in the sand by lunchtime. For travelers taking the ferry ride from St. Maarten, the Blowing Point Ferry Terminal opened in January 2023. 

Quinn is the newest addition to secluded Long Bay. The intimate hideaway boasts three suites that enjoy access to the amenities of the neighboring villa, Quintessence Hotel. Among them: an infinity pool, a spa and a wine cellar. Also, the Aurora Anguilla Resort & Golf Club (formerly the CuisinArt Resort & Spa) recently debuted on Rendezvous Bay with 178 suites, seven restaurants and a refreshed Greg Norman–designed 18-hole championship golf course. Adding to the lineup of amenities this year is the Aurora Entertainment Park with a lazy river, three water slides, a kids’ splash pad, cabanas and a swim-up pool bar.​

Cayman Islands

Sea stars can be found around Little Cayman Island.

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This three-island destination (Grand Cayman, Cayman Brac and Little Cayman) remains a Caribbean favorite. One standout addition 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, and a hot breakfast is included in the rate. Popular with Caymanians as well as guests is the hotel’s 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. 

In addition to the nonstop flights betweenLos Angelesand Grand Cayman, Cayman Airways also resumed service from Denver late last year, making it a cinch to jet from the mountains to the sands of Seven Mile Beach.​

Dominica

Trafalgar Falls is one of 12 waterfalls to see on the island of Dominica.

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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. Recently, 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, newcomer Coulibri Ridge 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 and a yoga pavilion, and complimentary high-speed Wi-Fi is available throughout. 

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

St. Lucia

The island of St. Lucia is known for its iconic volcanic peaks.

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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 fromNew York City. This winter, look for increased nonstop service from Atlanta, Miami, New York and Philadelphia on American, Delta and JetBlue.