Ocean View Club
Gaol Lane, Dunmore Town
Harbour Island is one of those quick getaways for East Coasters that's ideal for many reasons, the primary one being that there's nowhere to go (unless it's into the water). The life of the island revolves around the ocean: Playing in it, eating by it, drinking by it, fishing in it...add the fact that everyone in NYC seems to vacation there and you've got a pretty sizable social scene, too. Harbour Island is also great for kids, in part because it's sleepy and quaint and there really aren't any cars (except for a few taxis)—you access the island by boat. There are a few fancy resorts that dot the shoreline, but we're into Ocean View Club, a teeny tiny spot where all the rooms are done up individually, to pretty great effect. It also has a small and mighty restaurant, where you'll find significantly better fare than at many of the other spots on the island.
Playa Grande Beach Club
5 Aut, 33000, Playa Grande
On Dominican Republic’s slightly more wild north shore, interior designer Celerie Kemble and her financier husband wanted to create a low-key beach retreat that had the intimacy of a friend’s private home. Here, Kemble applies her playful aesthetic, a kind of Palm-Beach-meets-island-living-vibe to the immaculate grounds: there are high-back wicker chairs, ikat throw pillows, copper bathtubs, seagrass rugs and cane furniture. Each white-washed bungalow (there are six one-bedrooms and three three-bedrooms, best suited for families traveling together) has its own distinct feel and is lovingly curated with vintage pieces Kemble has hand-picked on her travels as well as those designed by local craftsman. Cool lattice-framed cabanas dot the lap pool, should you tire of the views on the mile-long private beach. Come evening, much of the activity centers around the Beach Club, which serves up a Caribbean-inflected menu and, of course, strong cocktails and a lively atmosphere.
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.
P.O. Box N7550 Paradise Island, Nassau
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.
Queen's Highway , BS, Gregory Town 1548
The only international property from the Enchantment Group (a.k.a. the good people who brought us Mii Amo), The Cove delivers on everything you'd want from a Caribbean vacation, starting with the pristine white sand, which you'll find in spades at the protected, private cove it occupies. The tranquil rooms, decorated in soft, gentle whites and neutrals, feature sliding doors that open directly out to ocean views framed by swaying palm trees. At 57 rooms, The Cove is much more intimate than their namesake resort, though it's unsurprisingly kitted out with an incredible infinity pool and spa. There are two excellent restaurants (and a wonderfully lazy bar) on site, but should you want to venture further afield, the candy-colored town of Harbour Island is a short ride away, and concierge can also organize every adventure imaginable, from kayaking to fishing to sailing.
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.
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.
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