Caribbean Hotels

Establishment neighborhood
The House
Paynes Bay, Bridgetown
Once you book, you are assigned to someone that basically looks after you throughout your trip. Your ambassador will do everything from picking you up at the airport, to getting you a rum punch, to setting up ‘jet lag revival’ massages upon arrival and arranging private dinners on the beach. Complimentary ice cream (we hear the house rum raisin is pretty insane), water and fruit by the pool and champagne breakfasts are nice perks. It’s a small place with only a handful of rooms and is adults only—so best for a couple.
Round House Inn
Though it lacks the glitz and grandeur of its high-end counterparts, Round House Inn is a worthy Barbados destination in its own right. Housed in a majestic, 19th-century colonial building overlooking the famous “Soup Bowl” break (legend has it, Kelly Slater caught some of the best waves of his life here), Round House features uninterrupted views of the Atlantic coast. Owners Robert and Gail Manley took great care to outfit each of the four natural coral-block guest rooms in subtle earth tones and wooden antiques, allowing the original architecture (skylights, deep-set windows) to take the spotlight. The no-frills atmosphere is undoubtedly inviting, but the main draw of this beachfront oasis is the eponymous Caribbean restaurant, which has locals, tourists, and guests flocking to its outdoor patio in droves. The homemade banana bread, Bajan pumpkin fritters, and flying fish and breadfruit soup—a wonderfully fragrant national dish—are not to be missed.
Sugar Beach
Val des Pitons, Soufriere, St. Lucia
One you arrive to Sugar Beach, you won't really want to leave—and that's kind of the point. Flanked by St. Lucia's twin volcanic Pitons, the property, tucked away on the island's west coast, is set amongst 100 acres of rainforest (meaning hummingbirds and butterflies are par for the course). Admittedly, it's a bit of a journey to get here, whether you fly in from the north or the south of the island, the road is steep and windy, but it's well worth the hour-long-drive. The recently renovated colonial-style cottages are the move—they're perched on the hillside and have their own claw-foot tubs, terraces as big as New York apartments, and are swathed in entirely in white from the slipcovered furniture to the four-poster beds. Each room has a private plunge pool,if you’re feel too lazy to wander down to the Caribbean, but should you make the effort, it’s one of those resorts where the main activity is ordering piña coladas to your beach chair while taking in the epic view. The spa is a necessary indulgence here, as the seven treatment rooms are tucked into private thatched-roof tree houses,…
Sivananda Ashram
Paradise Island
As far as ashrams go, Sivananda's approach to yoga is as traditional as it comes. What separates it from the pack, though, is its otherworldly Paradise Island location. Flanked by dense tropical gardens and white-sand beaches, the retreat makes next-level nirvana seem totally achievable. But don't be fooled by the idyllic setting, the yogic lifestyle is fully immersive here: A 5:30am wake-up call marks the beginning of a jam-packed day consisting of two mandatory meditations, two yoga classes, lectures, chanting, and nature walks. Accommodations are humble yet comfortable and range from shared beach huts and dormitories to private tents and garden rooms. At mealtime, the fare is vegetarian and prepared fresh on-site. Be sure to check the schedule as they host really interesting retreats.
Dorado Beach, a Ritz-Carlton Reserve
100 Dorado Beach Dr., Dorado
Laurance S. Rockefeller’s dream to create a resort and natural sanctuary in Puerto Rico became a reality in 1958, when he opened his resort at Dorado Beach. Environmental conservation remains a priority at this 1,400-acre property, and outdoor activities range from an eleven-mile hiking trail to two golf courses with views of the surrounding mountains and sea. Rooms come with floor-to-ceiling glass sliding doors, deep soaking tubs, and outdoor showers, and some have private plunge pools or rooftop terraces. The spa has steam pavilions, warm and cool pools, and a tree house for massages.
The Ritz-Carlton, Grand Cayman
Seven Mile Beach, Grand Cayman
This far-reaching property offers all the trappings one might expect from a Ritz-Carlton resort, plus access to the azure waters and white sands of not one, but two coasts—the North Sound on one side and Seven Mile Beach on the other. While the kids soak it up at the on-site water park or participate in one of many eco-adventure activities (supervised, of course), adults can improve their backswing at the Greg Norman-designed golf course or book a treatment at the La Prairie Spa. There are five restaurants on the property (ranging from casual to swanky), but only one is run by Chef Eric Ripert. The seafood-centric Blue by Eric Ripert has a particularly well-curated tasting menu and is considered by many to be the best dining experience in the Caribbean.
The Inn at English Harbour
English Harbour
People rave about the service at this twenty-eight-room resort on Antigua, which feels like you are being personally hosted. With just twenty-eight rooms and no kids under ten allowed, it’s an intimate and peaceful getaway, as everything you might need is on the property. There's a large heated pool, tennis courts, a beachside restaurant, a private white sand beach, hammocks, snorkeling, a rum bar, plus an on-site a library. The look is England meets the Caribbean, with grand colonial style architecture—standout features are the strong mahogany four-post beds with contrasting airy white linens. Apparently, the old–fashioned rum punch at The Reef Bar is not to be missed.
Jamaica Inn
Ocho Rios
The resort is known for having the same feel now as it did when it opened (when Sir Winston Churchill used to come here to paint). Colonial-style cottages offset the tropical beachside setting that has a bit of a retro Jamaican feel—and there's croquet on the lawn. Blessedly, there are no TVs to be found. The rooms are as on the beach as it gets (open the door and step in sand) and they are happy to bring you breakfast on your veranda if you don’t feel like making it over to the palm-covered dining room.
Fair Prospect to Folly Rd., Anchovy Gardens, Port Antonio
You can be as private or social as you like at this resort, which feels like a village of waterfront villas. Most people spend the day lounging by the infinity pool overlooking the sea, but you can relax by the private pool in your villa for a more secluded experience. The rooms are newly refurbished, simple, and modern, keeping the gorgeous setting the focus, with features like outdoor soaking tubs and sun decks. The town of Port Antonio, where the resort is located, was a hotspot in the 60’s and part of the experience is checking out the restaurants, bars, and live music in town. Fun feature: If you get tired of the beach, there’s a screening room that you can reserve.
Viceroy Anguilla
Barnes Bay, West End
If you're looking to escape your social scene on the Upper East Side, don’t come to this chicest-beach-house-you-have-ever-seen, designed by Kelly Wearstler, where the look is more heels than flip flops. The restaurants and bars are a step above your typical Caribbean resort experience—fresh made pasta at the signature restaurant Cobà, frozen cocktails and hummus wraps at the Half Shell, and cocktails and sushi for a very buzzy happy hour at the Sunset Lounge. The two-story spa and cute boutique that features local jewelry designers makes it a fun place to come with girlfriends.
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