Where to Go This Winter in the Caribbean

The Caribbean islands are forever a reliable destination for a quick warm-weather escape.

Where to Go This Winter in the Caribbean

Beach Enclave Turks & Caicos will debut 10 new beachfront villas in January.

Courtesy of Beach Enclave Turks & Caicos

Few places have made me feel as content as the Caribbean islands I’ve visited, like Nevis and St. Bart’s. Is it that I feel like a happier, warmer version of myself? Or that I actually slow down long enough to savor a cocktail and a beach sunset or talking to the locals? The Caribbean has endless appeal, and this year is no different, though it requires testing and distancing (easier to do in a sparsely populated island environment).

We talked to travel experts to whittle down a list of some of the dreamiest places to go and most luxurious places to stay, whether it’s a week or longer: You can apply to stay for up to a year in Anguilla, and the same in Barbados.

All of these islands require negative COVID tests before you fly, and some require a second negative test upon arrival, among other travel requirements and restrictions. Please check current travel restrictions with local authorities or your travel advisor.


Why we love it: An impressive food scene with scenic beaches. There are more than 120 fine-dining options on a tiny island, just 16 miles long and 3 miles wide.

Anguilla can be combined with St. Kitts, Nevis, or Antigua for island hopping, or you can easily spend a week exploring the island’s offerings. It has been called the “foodie capital of the Caribbean,” with everything from sandy beach bars (try the Creole snapper from the grill at SunShine Shack) to global fusion at Veya Restaurant. Malliouhana, an Auberge Resort, remains one of the best upscale boutique options, after undergoing a massive renovation in 2014 (it first opened in 1984).

“My favorite beaches of Anguilla are on the western end, where Malliouhana is situated on the most beautiful stretch,” says L.A.-based advisor Vanessa Shapiro. “It has a boutique vibe with island glamour and Caribbean style—no attention to detail was spared when designing this incredible place. Everywhere you look, there are blossoming flowers and tropical fruit, and there is an incredible cascading infinity pool.”

This winter, the hotel will introduce lucid paddleboarding, where you can watch life below water from the transparent, ecofriendly boards. It has also partnered with a legendary local storyteller who will talk about Anguilla’s history and culture as the sun sets—cocktail in hand, of course. And it has developed a whole slate of wellness by the water activities: yoga, Pilates, beach volleyball, pool workouts, and more. Malliouhana reopens December 17.

In 2016, the 76-room Zemi Beach House opened in Anguilla and quickly became one of the island’s most popular hotels, especially for its Zemi Thai Spa House, centered around a 300-year-old wooden house shipped from Thailand. For those who want to stay longer, the two- and three-bedroom suites are great options, with kitchens, terraces, and plunge pools. If you really don’t want to leave, Anguilla launched WFHiA (Working From Home in Anguilla), where visitors can live, work, and play for up to a year. Zemi Beach House reopens December 14.

The Zemi Thai Spa House is inside a 300-year-old wooden house from Thailand.

The Zemi Thai Spa House is inside a 300-year-old wooden house from Thailand.

Courtesy of Zemi Beach House

Arguably the island’s most iconic property, Belmond Cap Juluca (which underwent a huge redesign and expansion after Belmond purchased it in 2017) is now open. Every room is beachfront, and for even more social distancing, there are stand-alone beach villas on Anguilla’s most beautiful sandy stretch. Guests can make private reservations for wine or rum tastings, sunset sailing, birdwatching, and more. While the Arawak Spa is closed for now due to COVID, guests can book a selection of private spa treatments.


Why we love it: For beach-obsessed travelers, Antigua offers the picture-perfect Caribbean dream scene with coconut palms and pristine white beaches. It’s also one of the best islands for families.

Jumby Bay Island, part of the Oetker Collection, is a private island two miles from Antigua, home to 4.5 miles of protected shoreline and one of the Caribbean’s most beloved resorts. “It’s perfect in every way,” says Will Kiburz, vice president at Coronet Travel. “It’s a truly five-star deluxe private island experience, with everything included. There’s no other place I’m aware of like this in the Caribbean.”

“Jumby Bay is especially great for the era of social distancing as the island never feels crowded, with endless beaches and the clear blue ocean steps away from anywhere you choose to relax,” says Nicole Gerber, a travel advisor based in New York.

Guests arrive via a short cruise to Jumby Bay in VIP-style on hotel boats from Antigua’s international airport. Then, think white sand beaches, bicycle paths, and zero cars—plus the most delicious all-inclusive dining with multiple restaurants and poolside bars, all sorts of water activities and sports, and the Jumby Bay Spa, offering organic Tata Harper signature treatments. Weekly cooking classes focus on local eats like crab cakes, raisin fudge, and coconut drops—and are also included in the rate. The Jumby Explorers Kids’ Club allows kids to learn about conservation efforts to save the local Hawksbill turtles and even adopt their own. The property is an all-suite property, with 28 totally refurbished suites, 22 private residences, and 14 villas, so it’s another great option for staying longer.

Carlisle Bay, where almost all 82 rooms have beach views, is a wonderful family-friendly option on Antigua. The resort focuses on tennis—there are nine courts and complimentary weekly tennis clinics.

Jumby Bay is a private island retreat off the coast of Antigua.

Jumby Bay is a private island retreat off the coast of Antigua.

Courtesy of Jumby Bay


Why we love it: The island known for rum punch and relaxation also draws a big jet-setting crowd. You can visit Mount Gay, the oldest continuously run distillery in the world. There are wilder waters for surfing on the Atlantic side and snorkeling in the calmer waters of the Caribbean.

Family-owned Cobblers Cove reopened last year, after a five-year renovation, with 40 refreshed suites, a new coral pink-and-white color scheme by owner and designer Sam de Teran, and a partnership with furniture company Soane Britain.

Will Kiburz recommends Sandy Lane as “an iconic Caribbean property.” The 113-room property evokes an Anglo Caribbean feel (as does much of the island itself) in design, colonial architecture, and afternoon tea. There is near-perfect service and a 47,000-square-foot spa. It is the most storied property on the island, thanks to countless high-profile visits, including Prince Harry and other British royals; it was also the site of Tiger Woods’ wedding.


Why we love it: Jamaica has kept its distinctive and soulful culture, with a musical and food heritage unlike any other island. The hotels range from toes-in-the-sand laid-back to super-luxe.

There is such a legacy with the hotels on Jamaica,” says Katie Cadar, director of leisure sales at TravelStore. “Picture Noel Coward leaning on the bar, or JFK and Jackie, or Paul McCartney.”

And James Bond, too. Or at least Ian Fleming, his creator, whose home-turned-resort, GoldenEye, will help to celebrate the release of the 25th Bond film in April 2021. You can even book Fleming’s original five-bedroom home, which includes his writing desk. He created the Bond character while visiting Jamaica, once saying, “Would these books have been born if I had not been living in the gorgeous vacuum of a Jamaican holiday? I doubt it.”

The 132-room (including 27 private villas) Round Hill Hotel and Villas also brings the glamour. “There is a casual elegance, and I love the green striped awnings and black-and-white checkerboard floors,” says Cadar. “I always picture a British actor in a white suit and straw hat standing by the beach bar, or heading into afternoon tea. You have to appreciate the history of Round Hill and the many guests who have owned villas or chosen to stay there.” This is where John and Jackie Kennedy spent part of their honeymoon and where Ralph Lauren played a big part in design (and owns property).

For something smaller, but no less chic, try Strawberry Hill, a 12-cottage mountaintop retreat owned by Chris Blackwell, the founder of iconic Island Records, which has supported Jamaican music and artists, including Bob Marley (who spent time here in the 1970s), but also famous heavy hitters like U2, Queen, Cat Stevens, Leona Lewis, and many more. Here, it’s more about mountain air, wildlife viewing, and hiking trails rather than beach vibes.

Strawberry Hill is a refreshingly different and chic mountain retreat in Jamaica.

Strawberry Hill is a refreshingly different and chic mountain retreat in Jamaica.

Photo by Island Outpost

St. Bart’s

Why we love it: It is impossible not to fall in love with St. Bart’s, for its unspoiled landscapes and beaches, but equally its restaurant scene and shopping. You feel like a better version of yourself on St. Bart’s, but the scene isn’t snooty, just inspiring.

Will Kiburz books different hotels depending on the type of traveler. “We love Eden Rock for the scene, staff, and villas, and Le Toiny for honeymoon clients who don’t need to be on the beach. And we love Le Barthélemy for a more quiet and understated scene,” he says.

If you’re missing Europe, you can get your fix on St. Bart’s, says travel advisor Michael Schertz, who is based in New York City. “I always tell my client that it’s a piece of the south of France that just so happens to be located in the Caribbean.”

There is a highly anticipated newcomer on the island, the Hotel Barrière Le Carl Gustaf, from the French-owned Barrière Group, known for luxe properties all over France. The 21-room hotel is on a hillside in Gustavia (the biggest town, where most of the island’s restaurants are clustered); it offers cottages and villas, each with its own private pool and terrace. Though the hotel is not oceanfront, Shellona Beach is a five-minute walk away. There is an outpost of Fouquet’s, an island version of the famous brasserie in Paris, and the spa uses all Biologique Recherche products in its facials.

The newest luxury hotel on St. Bart’s

The newest luxury hotel on St. Bart’s

Photo of Hotel Barrière Le Carl Gustaf by Fabrice Rambert

Schertz recently returned to one of his favorite hotels, Eden Rock, an Oetker Collection property, and was impressed with the new procedures in place. “It felt subtle but noticeable—and the frosé stand on the beach was still rocking.” Eden Rock also announced a partnership with Tradewind Aviation that will make it seamless and easy to travel from anywhere in the United States via San Juan, Puerto Rico, to St. Bart’s on a private plane. “This partnership can’t be beat,” Schertz says. “You [even] get to clear customs quickly in Puerto Rico. You need to be at the airport an hour prior to departure, but I was running late and Eden Rock called Tradewind Aviation and asked them not to close the check-in. Where else can you do that?”

Katie Cadar calls Cheval Blanc her favorite property on the island. “It has the best beach, fabulous views, and great service, but still only a short drive to Gustavia. It’s so beautiful,” she says. The 61-room resort sits on Flamands Beach and evokes French West Indies flair with a signature blush pink throughout. Villa de France, a five-bedroom dream residence, has direct access to the beach and an infinity pool. Chef Jean Imbert oversees the restaurant and also designed the resort’s tableware in collaboration with Dior.

“Cheval Blanc exudes elegance,” says travel advisor Kristina Miller, who is based in Fort Lauderdale. “I especially love the perfume bar at the spa where you can create your own signature scent. It makes the most special souvenir to remember your trip long after you’ve come home.”

Turks & Caicos

Why we love it: Aside from the stunning resort options and perfect beaches, safety is the new luxury—the team at Amanyara says guests have been reassured by Turks & Caicos’s TCI Assured program, which adds a sense of safety.

With all the options on Turks & Caicos, it helps even more to work with an expert. “Como Parrot Cay and Amanyara are our top choices for Turks,” says Will Kiburz. “We love them as they are super deluxe and removed from Grace Bay, with more privacy. The Shore Club and Grace Bay Club work great for our clients looking for better value with lots of great dining and things to do within walking distance.”

For an alternative to the larger resorts, Dallas-based advisor Steve Harris recommends Beach Enclave, which calls itself a villa-resort. “It speaks to the privacy and seclusion travelers are requesting, with private residential villas that come with a butler, chef, and concierge services. The original units are on the North Shore, but there are now five new units along Long Bay beach and more opening soon on Grace Bay beach.” The 10 new stand-alone villas on Grace Bay are the first newly built project on Grace Bay Beach in more than a decade.

Como Parrot Cay is located on its own private island, with a six-mile-long beach. SmartFlyer’s Erina Pindar just returned from a trip to the hotel. “Parrot Cay’s Southeast Asian–inspired approach to cuisine and wellness is second only to its white sandy beach and crystal-clear water,” she says. “The newly updated beachfront villas are just steps from the ocean and a few minutes’ walk from the beach club, with family and adults-only pools. The island is rich in marine life and clients love to explore by paddleboard, looking out for turtles, nurse sharks, and barracudas along the way.”

The hotel is big on wellness—Pindar calls the spa the one thing not to miss. Como’s Shambhala Retreat has a long list of options, including Shirodhara, an Ayurvedic treatment to improve focus and concentration. For the animal lover, Pindar recommends arranging a visit to Potcake Place, a charity devoted to finding good homes for puppies born on the streets in Turks & Caicos. About 500 puppies are adopted through Potcake Place each year, but visitors can take them on short walks without the bigger responsibility of taking one home.

Como Parrot Cay not only has a fabulous beachfront, but also two beautiful pools.

Como Parrot Cay not only has a fabulous beachfront, but also two beautiful pools.

Courtesy of Como Hotels & Resorts

Amanyara, set on the shores of an 18,000-acre nature reserve on the island of Providenciales, has seen an uptick in family and friend “pods” booking their stand-alone suites and villas. “Amanyara feels like a place you spent 48 hours traveling to, but only had to hop a short flight or two, depending where you’re based, from the U.S. to reach,” says Florida-based travel advisor Lesley Cohen. “There are clear waters and white sand beaches all over Turks & Caicos, but it feels dreamier and more exclusive at Amanyara.”

This month, the hotel is showing off all 38 newly refurbished pavilions in its reopening ahead of its 15th anniversary next year. (Cohen says they feel straight out of the pages of Architectural Digest.) While Aman has always been wellness focused, it is also launching wellness programs in 2021 that were sidelined due to COVID; they include customizable programs for stress and mental health management, weight loss and management, and detox/cleansing.

>>Next: The Best Luxury Hotels That Actually Opened in 2020

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