Flee Winter (And Crowds!) at These 5 Under-the-Radar Caribbean Island Destinations

Score an uncontested beach chaise and a wintertime tan at these brilliant off-the-grid holiday spots.

Is it freezing where you are? Well, that means it's the perfect time to dream up a pristine beach vacay — and not the same one as everyone else you know. Skip the crowds and consider one of these five Caribbean island destinations for a zen winter getaway — where tourist crowds are scarce and vistas are beyond stunning.

1Port Antonio, Jamaica

Popular resort hot spots like Montego Bay and Negril may command most of the attention, but if you want a more tranquil Jamaican experience, head to the lush landscape of Port Antonio. 

As the capital of Jamaica’s “garden parish” of Portland, Port Antonio offers nonstop natural wonders, from waterfalls to rainforests. Located on the northeastern coast of the island and edged by the Blue Mountains, Port Antonio is a haven of old school villas and laid-back charm.

Float on a bamboo raft along the Rio Grande valley, frolic in the tree-lined Blue Lagoon and then relax like a Bravoleb in the hillside villas at Goblin Hills with views of the crystalline water of San San Bay. Check out the Tree Bar, fittingly nestled in the trunk of a towering ficus tree and lined with strings of twinkling lights. For a more rock-star-esque ambiance, head to Geejam Hotel. Buried deep in the rainforest, the hotel's seven quietly luxurious rooms (as well as the private recording studio) are a favorite retreat for the likes of Drake, Gwen Stefani, and Grace Jones.

2Anse Chastanet, St. Lucia

Perched high on a bluff, Anse Chastanet unfolds like a green carpet to paradise. St. Lucia is noted for unparalleled beauty and this unusual resort supplies in-your-face views of the island’s striking landscape. Set on 600 acres that display coconut palms, tropical flowers, two secluded beaches, and staggering vistas of the twin-peaked Pitons, the scenery is as much a part of Anse Chastanet as the 49 art-filled rooms.

Guests are enveloped in natural opulence that includes rooms with the fourth wall missing — showcasing up-close panoramas, balconies wrapped around blossoming trees, and tiled patios that stretch out to the Caribbean Sea. Electricity, phones, TV, and Wi-Fi are banned from rooms to ensure optimum peace and relaxation.

Neighboring Jade Mountain resort ups the game with “sanctuaries” adorned with 15-foot ceilings and private infinity pools, guaranteed to melt away any memories of snow storms and stress-filled days.

3Eleuthera

Blanketed with pineapple fields and pink-sand beaches, Eleuthera beckons visitors with old world charm and dreamy scenery. At just two miles wide and 110 miles long, this sliver of a Bahamian out island provides outsized enjoyment. Noted for entrancing cliffs that fringe the eastern side of the island as well as local traditions like bonefishing and sailboat racing, Eleuthera boasts laid-back experiences that will untighten the knottiest of muscles.

Although celebrities like Lennie Kravitz and Mariah Carey own homes on Eleuthera, most of the island remains low key and unspoiled. Many of the resorts have fewer than a dozen rooms, ensuring that you’ll never have to stake out a beach chair. Lounge in ocean front villas or cottages surrounded by native Kamalame trees at The Cove, or sink into the sight of a rosey-hued, crescent-shaped beach from a verandah at Pineapple Fields Resort and then head to the property’s popular local hangout, Tippy’s Beach Bistro, for fresh seafood and dancing.

4Islet Oscar, Martinique

Hop a 15-minute boat ride from the Martinique mainland and you’ll arrive on the tiny islet that boasts a historic guest house with four colonial-style bedrooms that supply the island’s only accommodations... which means that if you book all of the rooms, you’ll be kicking back on your own private island, with only the restaurant’s reserved dinner guests as occasional visitors.

Surrounded by shimmering water and open rooms filled with rustic details and canopy beds with mosquito nets, Islet Oscar is like a castaway’s paradise. Fresh, creole style dishes focusing on local fish and fruits and a gentle sea breeze that constantly sweeps over the island creates an idyllic vibe that’s hard to resist. Recline in the living room made from banana fiber sheets and listen to the gently lapping sea for the ultimate private island experience.

5Barbuda

The sister island to Antigua, Barbuda boasts more plants and wildlife — notably the frigate bird colony — than people. Mostly untouched by tourism, the pearl and pink sand beaches as well as the undeveloped terrain help Barbuda standout from most other islands.

A favorite of Princess Diana, the island remains off the beaten path with just three hotels, including Coco Point Lodge, with discreet, beachside cottages dotting a 164-acre peninsula, and Barbuda Belle, which has just seven bungalows surrounded by mangroves and a 15-mile stretch of beach.

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