9 Caribbean Resorts to Beat Your Winter Blues

If the idea of a Caribbean getaway immediately conjures images of turquoise seas and white sand, well, that’s fair. After all, the region is one of the world’s quintessential vacation spots. But the beaches are only part of the story. Comprising hundreds of islands, 13 independent nations and a smattering of other territories and dependencies, the Caribbean offers a surprisingly diverse array of experiences—with resorts that are just as varied.

You can embrace French glamour in St. Barts, play croquet in the British territory of Anguilla, sample bean-to-bar chocolate in Saint Lucia or dive deep into literary history in Jamaica. The following nine resorts run the gamut from historic to forward-looking, classic to modernist, with activities that include yacht rides, rounds of golf and cooking classes. Oh, and those out-of-this-world beaches? They’re a given.

Cap Juluca, A Belmond Hotel, Anguilla (Anguilla)
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Marked by whitewashed walls, plastered columns and courtyards with mosaic tiling, this member of the Belmond portfolio draws design inspiration from Greco-Moorish architecture and is meant to evoke Moroccan riads. On-site activities include basketball, pickleball and tennis, and there’s a croquet lawn that will remind you Anguilla is a British Overseas Territory. The alfresco Cip’s by Cipriani nods to the hotel’s sister property in Venice, while the casual Cap Shack bar, set on the sparkling sands of Maundays Bay, is a lovely spot for snacking to the sounds of calypso and reggae tunes.

Grace Bay Club (Turks and Caicos)
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The Mediterranean-inspired Grace Bay Club sits on Grace Bay Beach, often ranked among the world’s best beaches. Choose between the adults-only Hotel, the family-friendly Villas Suites and the luxe resort-within-a-resort known as The Estate. There’s a queen conch and a spiny lobster on the Turks and Caicos national flag, so you know the seafood must be good in these parts. It just so happens the resort’s Infiniti Restaurant & Raw Bar is one of the best places in Providenciales to try some.

Eden Roc Cap Cana (Dominican Republic)
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On the eastern tip of the Dominican Republic, this Relais & Châteaux property comprises thatched-roof oceanfront bungalows, suites with private pools and sprawling villas that sleep between seven and 24 guests. Eden Roc is particularly popular with food lovers, thanks to a roster of restaurants that includes Blue Grill & Bar for seafood, Mediterraneo and more, plus an elegant cocktail lounge called Riva Bar, inspired by 1960s Monte Carlo. Beyond restaurants, culinary experiences include mojito-making workshops, rum and chocolate tastings, and classes that will teach you to make anything from sushi to the island’s beloved plantain-based mofongo.

Le Barthélemy Hotel & Spa (St. Barts)
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St. Barts is known for its French sophistication, and this polished yet playful resort fits right in. After all, it’s the brainchild of a Parisian designer and French chef, who ensure it’s up to Gallic standards. Set on a curving stretch of sand called Grand Cul-de-Sac, Le Barthélemy is home to the only Spa La Mer in the Caribbean. It also has Abyss, where chef Jérémy Czaplicki, who helmed award-winning restaurants in France, brings a fine-dining ethos to the French-Caribbean menu. Be sure to order the house champagne; bottles are aged under the surface of the Atlantic Ocean.

Four Seasons Resort Nevis, West Indies (Saint Kitts and Nevis)
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The Four Seasons brand made its first foray into the Caribbean with this West Indies outpost 33 years ago. In 2019, the resort finished a complete overhaul that saw the addition of seafoam-green botanical wall covers and geometric carpets that evoke the stained-glass windows in many Nevis churches. The property sits on the site of a 1790s coconut and sugar plantation, and history abounds at every turn: You can see the ruins of an old stone windmill from the golf course or take a guided tour of significant sites from the life of Alexander Hamilton, the island’s most famous native son.

Jumby Bay Island, Antigua (Antigua)

A 10-minute yacht ride whisks you to this 300-acre private island paradise off Antigua that’s centered around a circa-1830 property. Once you arrive, the experience is all-inclusive, from meals and water sports to free-flowing cocktails and Taittinger champagne. Suites take advantage of the permanently pleasant weather with open-air bathrooms, and some include private pools. But the Caribbean Sea and its diverse fauna are the stars of the show here. Adults can snorkel, kayak, paddleboard or sail, while kids can learn about hawksbill turtles and even see them hatching.

Jade Mountain Resort (Saint Lucia)

This architectural marvel sits on a cliffside overlooking Saint Lucia’s twin volcanic spires, the Pitons. The owner, who is also an architect, kitted out the 29 “sanctuaries” with tropical hardwood, local stone and Barbadian coral finishes—and 24 come with private infinity pools. In each, ceilings soar to 15 feet, and the fourth wall is missing to allow for truly uninterrupted views. Guests at Jade Mountain also enjoy access to sister property Anse Chastanet Resort for even more dining options. The two hotels are separated by more than 2,000 cacao trees, and chocoholics can take part in tours, tastings and truffle-making classes.

Silversands Grenada (Grenada)

Looking out over Grand Anse Beach, this Spice Island resort features a roughly 330-foot infinity pool (said to be the longest in the Caribbean), plus rooms and villas oriented to the west to maximize sunset views. When you’re not relaxing in the spa or sampling rare and small-batch rums at Puro, the resort can set you up on adventures around the island, including diving to the world’s first underwater sculpture park, hiking to waterfalls and moonlight kayaking in an illuminated boat. Silversands also recently expanded with the boutique Beach House, where 28 canopied suites dot a cliffside and adjacent beachfront.

GoldenEye (Jamaica)

If the name of this Jamaican resort rings a bell, that’s because it’s the former estate of Ian Fleming, who wrote all the James Bond novels here. Set among tropical vegetation, it was also a hideaway for musicians like Sting and Bono for a time. Island Records founder Chris Blackwell eventually acquired the property and added cottages and beach huts to the villas. Skip a Vesper martini and opt instead for rum and jerk barbecue at the Bamboo Bar, and save time for a FieldSpa treatment, which uses flowers, roots, leaves and herbs grown on the resort’s farm.

Lead photo courtesy of Eden Roc Cap Cana.