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5 Caribbean Getaways to Escape Westchester Winters

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Photo courtesy of Rosewood Little Dix Bay

Escape from the cold Westchester winter and head where it’s sunny at one of these five gorgeous Caribbean getaways.

By Andrew Dominick, Samantha Garbarini, Maya Ono, Gina Valentino, and Nicole Russo Steinthal

Caribbean pool

The view from a one-bedroom pool-suite terrace at Rosewood Little Dix Bay. Photo courtesy of Rosewood Little Dix Bay

Virgin Gorda

Magic Hour is 4 p.m. at Rosewood Little Dix Bay (rosewoodhotels.com/en/little-dix-bay-virgin-gorda) on Virgin Gorda. Afternoon sunlight spills down the half-mile crescent beach, lined with cushion-topped loungers. The translucent water laps against the shore, while nearby sea turtles break the surface as they come up for air, alerting snorkelers to their presence. Beach attendants stroll the sand with ice-cold waters and potent rum-based Painkillers, while honeymooners line up at the house-made ice cream stand that pops up around this time each day.

Caribbean bar

Photo courtesy of Rosewood Little Dix Bay

Founded in 1964 by conservationist Laurence Rockefeller, Little Dix Bay drew a well-heeled crowd (Queen Elizabeth II and Prince Philip famously vacationed there) until Hurricane Irma shuttered the resort in 2017. Four years and a sustainably minded remodel later (you won’t encounter a single plastic bottle on the premises), the resort reopened with a design that preserved the original character, including the conical roofs of the 80 rooms, suites, and villas, tucked so smoothly into the tropical vegetation.

Caribbean water

Photo courtesy of Rosewood Little Dix Bay

Speaking of the suites, they’re almost as impressive as the beachfront — particularly the spacious Tree House Suites, with wraparound terraces at the tree line, and the One Bedroom Pool Suites, with private plunge pools overlooking the bay. Whatever category of room you choose, you’ll have butler service to cater to every whim, whether that’s unpacking your bags, setting up appointments at the clifftop spa, or ensuring you eat well at the on-site restaurants, from the waterfront, farm-to-table Reef House to the romantic, tapas-focused Sugar Mill. (Don’t miss the Rum Room, either, with more than 100 iterations of the spirit.)

ocean side bedroom

Photo courtesy of Rosewood Little Dix Bay

Your butler can also arrange off-property excursions, including to the boulder-strewn Baths at Devil’s Bay National Park. Don’t miss the complimentary beach drops, which ferry guests to the beaches, like Valley Trunk, where it’s not uncommon to have a little slice of paradise all to yourself.— SG

Seasonal rates from $1,140.

Saint Barthélemy

Esteemed American businessman and superyacht owner Herb Chambers once said in an interview that “Our lives are too short to pass up cruising and vacationing on St. Barts.”

roof top suite

Photo courtesy of Hotel Barriere Le Carl Gustaf

After visiting the illustrious French West Indies Island, you may discover the profound truth in Chambers’ declaration.

The hotspot has long been the exclusive playground of the world’s elite, with an inimitable yet authentic air that flows from a seamless mélange of European elegance and Caribbean charm. Experience azure waters with pristine “white-sugar” sand beaches, a quaint and accessible downtown dotted with sophisticated shops and delectable dining, and abundant luxe accommodations and recreational offerings. These are the keys to paradise.

Discover the art de vivre at Hôtel Barrière Le Carl Gustaf (hotelsbarriere.com/fr/saint-barth/le-carl-gustaf.html). Like the island itself, the luxury property (part of France’s Barrière Group) exudes understated elegance. The hotel’s 21 rooms, including bungalows, suites, cottages, and villas, were designed by renowned French design firm Gilles & Boissier, for whom no detail was too insignificant.

The Villa Diane boasts three suites overlooking Gustavia Bay, each brimming with amenities (electrically operated blackout shades in the bedrooms, a 900-square-foot bathroom outfitted with Italian marble, a minibar stocked with French wines, oversize closets/changing rooms, and expansive living and entertaining areas indoors and out). The private terraces and infinity pool face the yacht-studded bay and buzzing capital, providing a fantastical escape.

Caribbean pool dining

A compound of private bungalows makes up Hôtel Barrière Le Carl Gustaf and overlooks Gustavia—St. Bart’s port town, replete with swanky bars and shops. Photo courtesy of Hotel Barriere Le Carl Gustaf

For on-site dining, Le Fouquet’s (by Michelin-starred French chef Pierre Gagnaire) crafts a breakfast tower overflowing with fresh fruits, pastries, and charcuterie; cocktails spritzed with novel fragrances; and flavorful local seafood dishes and pastries to finish.

Not to be missed are the local experiences: a massage at the on-site Diane Barrière Spa, a morning at Shell Beach, lunch at the elevated Shellona restaurant, topped off with an evening cruise on St Barth Sailor’s Good Life catamaran. While gliding along the dazzling waters, cocktail in hand, admiring the sun as it slips into the horizon, it might be a fitting to reflect on the Hôtel Barrière Le Carl Gustaf staff’s initial greeting: “We always say that it may be one’s first time to Saint Barts, but it won’t be their last.” —GV

Seasonal rates from $762.

San Juan, Puerto Rico

Live in the sunshine, swim the sea, drink the wild air.
—Ralph Waldo Emerson

When Emerson wrote that, he must have envisioned something like Puerto Rico’s Condado Beach area.

A sub-barrio of Santurce, Condado is an oceanfront escape with public beaches, teal-blue water views, and white-sand beaches in every nook and cranny. And depending where you elect to stay on your breezy, sultry escape, the Atlantic Ocean is your backyard.

Caribbean hotel

The Condado Vanderbilt, opened in 1919, was Puerto Rico’s first luxury hotel. Designed by the architects of Grand Central Terminal, both the interiors and exteriors lend an air of quiet sophistication. Photo courtesy of Condado Vanderbilt

If tropical luxury is what you seek, the Condado Vanderbilt (condadovanderbilt.com) is your remedy for relaxation. Guestrooms and suites mostly provide sea views, but if you have a city scene, fear not, because out back you’ll find stunning ocean views and plenty of lounge chairs on which to soak up the sun.

beachside hotel

Photo courtesy of Condado Vanderbilt

When you do get toasty, take a dip in one of many pools. The West Tower boasts a 200-foot mirrored pool with a waterfall and a separate infinity pool that overlooks the Atlantic. Over in the East Tower, there are three smaller pools with cocktail service and a more private beach area just off the pool deck.

Because the Condado Vanderbilt should be about spoiling yourself or that special someone, there’s a highly rated spa on the premises that offers massages (including couples), facials, body wraps, manis and pedis, and even Cryo-T shock treatments.

beachside hotel room

Photo courtesy of Condado Vanderbilt

Prior to dinner, enjoy a strong cocktail, fine cigar, or both in the for-hotel-guests-only Avo Lounge. Just don’t get too full on spirits and snacks. When it’s time to dine, treat your taste buds to an a la carte, four-course tasting, or the chef’s tasting menu at 1919. Chef Juan Jose Cuevas — a Blue Hill at Stone Barns alum — doesn’t only bring it in terms of taste and stunning plating; he does it with local, organic ingredients that impress. Regardless of any other experiences you may choose, you must eat here.

pool by beach

Photo courtesy of Condado Vanderbilt

If the Vanderbilt isn’t your deal, however, Condado Ocean Club’s (condadooceanclub.com) adults-only Miami vibes might be. This swanky, modern hotel isn’t only about ocean views, cabanas, and pools. It’s a party on weekend nights, with DJs, dancing, and piña coladas from the outdoor bar, but that’s after a meal at one of their two on-premises restaurants or a strong-but-smooth Japanese whiskey cocktail and Asian-inspired tapas at Jade.

Caribbean dining

The all-adult 96-room Condado Ocean Club features a poolside bar, classic Puerto Rican dishes with a modern twist at SOCIAL, and rooms with floor-to-ceiling views. Photo courtesy of Condado Vanderbilt

Whether you choose the Ocean Club or the Vanderbilt, do so knowing it’s a short, seven-or-so-minute (and dirt-cheap) Uber to all the culture, restaurants, bars, art galleries, stunning architecture, and hospitality that Old San Juan has to offer. —AD

Seasonal rates from $246 (Condado Ocean Club) and $319 (Condado Vanderbilt).

Curaçao

Step off the plane at Curaçao International Airport and onto a sunny, beachy paradise, rich with history, culinary excellence, and art at every turn. This southern Caribbean island, 40 miles north of Venezuela, is accessible via nonstop flights from JFK. You may be greeted by smiling locals wishing you bon bini, or “welcome” in Papiamentu, the local dialect. (The vast majority of Curaçaoans speak three languages in addition to Papiamentu, including English, Spanish, and Dutch.)

Caribbean housing

The capital city of the Dutch Caribbean island Curaçao is Willemstad, known for its old town center, with pastel-colored Colonial architecture. Photo courtesy of Diamond Public Relations

One of the main attractions of Curaçao is its beaches, famous for crystal-clear waters and cove-like limestone cliffs cocooning white, sandy shores. Willemstad, the capital, is a designated UNESCO World Heritage site for its historic buildings, including the oldest standing synagogue in the Americas, Mikvé Israel-Emanuel, aka Snoa. Jewish heritage in Curaçao is amplified by the massive May Henriquez estate, once owned by Max Frederic Henriquez and May Henriquez and current home of the Landhuis Bloemhof art gallery and museum. The estate is also where you’ll find Number 10 cafe, humming with the sound of piping-hot espresso brewing and orders for fresh sandwiches, salads, and house-baked goods.

The Caribbean

A bird’s-eye view of Papagayo on Jan Thiel Beach. Photo courtesy of Diamond Public Relations

Additional culinary attractions not to be missed are The Pit Smoker (thepitsmoker.everyorder.io), Ceviche 91 Gastrobar in Willemstad (Instagram.com/ceviche91curacao), Nulfwinfig (restaurant020.com/en), and other bars and restaurants in the trendy Historic Pietermaai District (pietermaaidistrict.com). Don’t forget to snag a bottle of Curaçao’s blue liquor, which can only be made on the island. Visitors can choose a Dutch resort experience at the exclusive Papagayo on Jan Thiel Beach, offering both rooms and villas (papagayao.com), or a more American-leaning experience in downtown Willemstad, at Renaissance Wind Creek Curaçao Resort (renaissancecuracao-resort.h-rez.com). When in doubt, local native Tirzah Statia, dubbed the Mayor of Curaçao, can be reached via the Curaçao tourist board (curacao.com/en). —MO

Caribbean hiking

On the way to Santa Martha Beach is an overlook point with a unique view of the bay. Photo courtesy of Diamond Public Relations

Seasonal rates from $245 (Papagayo on Jan Thiel Beach) and $196 (Renaissance Wind Creek Curaçao Resort).

Barbados

Sitting on layers of coral pushed out of the ocean hundreds of thousands of years ago, Barbados is one of the Caribbean’s most beautiful and sought-after destinations. The island’s shimmering white sand and bright, turquoise water welcome each guest to this British Commonwealth republic, which gained independence in 1966. Barbados sits south of the main hurricane belt, so it is the perfect year-round tourist destination. Although the island is divided into 11 parishes, most of the Island’s hotels are on the southern and western coastlines. It is commonplace to be able to roll right out of bed and onto the beautiful sand.

Caribbean massage

The 5,600-square-foot Acqua Spa at O2 is the quintessence of luxe tranquility. Photo courtesy of O2 Beach Club

The new luxury all-inclusive resort, O2 Beach Club & Spa (O2beachclubbarbados.com) stands out for its incredible service and four on-site gourmet restaurants. (In keeping with its British heritage, high tea is served daily at 3:30.) The Acqua Spa at O2 is outstanding and a perfect combination of luxury and tranquility.

Caribbean pool

Located on Barbados’ southern coast, the opulent O2 Beach Club & Spa Luxury Collection offers adult-only suites with private balconies. Photo courtesy of O2 Beach Club

Another all-inclusive hotel is The Sea Breeze Beach House (sea-breeze.com), offering a relaxed vibe for families with younger children. The excellent Sea Breeze team organizes daily activities for children, including a kids’ club, game room, and varied watersports. There is also an authentic rum shop on the premises that serves signature Bajan rum punch, as well as gourmet coffees, local juices, and Bajan pastries.

The island’s many activities and excursions appeal to both couples and families. The Cool Runnings catamaran tour (from $95; coolrunningsbarbados.com) is a don’t-miss. It’s a five-hour lunch or dinner sail around Barbados, with time to swim and snorkel with the sea turtles. For more outdoor fun, try the Island Safari Jeep off-road tour (from $65; islandsafari.bb), offering an afternoon of sightseeing around all 11 parishes, including amazing rock formations and cliff views.

Caribbean jungle

The Island Safari Jeep off-road tour promises fun and a spark of adventure. Courtesy of Island Safari

Barbados is the birthplace of rum, so a visit to the award-winning Foursquare Distillery is advised. Set on a majestic sugarcane plantation from the 1700s, it’s the only remaining family-run, rum-producing company on the island and one of only two distilleries still owned by a Barbadian family. The rum-tasting bar is open year-round, with 30 different types of rum to sample.

Dining on the island is plentiful, with outdoor food markets and restaurants perched seaside for first-rate seafood and barbecue. Tapas Barbados (tapasbarbados.com) is an excellent restaurant in the island’s capital of Bridgetown, overlooking the water’s edge. For the best fish tacos, plus remarkable piña coladas and daiquiris, visit Cocktail Kitchen (ckbarbados.com).

Barbados is an island paradise only four and a half hours by plane from New York. — NRS

Seasonal rates from $613 (O2 Beach Club & Spa) and $597 (The Sea Breeze Beach House).

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