Seven (Sorta) Hidden Caribbean Winter Getaways

What are you still doing in Boston?!?!? Finding your own private island is easier than you think.

Additional reporting by Stefanie Schwalb and Jolyon Helterman

Photo via Maridav/Alamy Stock Photo

You know the drill: Right now in Boston, it’s cold. It’s dark. As much as we love this city, even we have to admit that January might be the one month of the year when it’s totally okay to rue living here just a little bit. Thankfully, paradise does exist, in the hidden (and not-so-hidden) nooks and crannies of the Caribbean. So throw a bathing suit on under your puffer coat and high-tail it to Logan—getting away is easier than you think.

Photo by Roy Conchie/Alamy Stock Photo


When somebody mentions the French West Indies, most people think of St. Barth, with its mega-yachts, celebrities, and billionaires. A much quieter but no less French alternative is Martinique, a tropical paradise with an active volcano (don’t worry, it’s safe to visit), rainforest, black-sand beaches, and some of the best Creole cuisine in the world. Technically part of France, the currency is the euro, and the vibe is French without the fuss. The vibrant capital, Fort-de-France, boasts colorful colonial architecture and streets lined with boutiques, cafés, and art galleries, but there’s plenty of nature to explore.

Ritzy Nights: French Coco, which opened in 2016, is a five-star resort isolated on the Caravelle Peninsula, abutting a nature preserve but still within striking distance of dining and nightlife.

Family Excursion: Take a break from the beach to visit Jardin de Balata, an expansive horticultural garden with more than 3,000 species of tropical plants.

One-of-a-Kind Adventure: The town of Saint Pierre was built on the remains of the former capital, which was wiped out by a volcanic eruption in 1902. The one-room Musée Frank A. Perret offers a scintillating glimpse into the tragedy and its aftermath.

Top Tables: The bakeries on Martinique rival the best in Paris, so stop by for fresh croissants in the morning or a baguette for a picnic lunch. And if you’re feeling homesick, check out the local cuisine at La Baraqu ‘Obama Bar, Restaurant, Grill, whose name pays homage to the 44th U.S. president.

When the Sun Goes Down: Like elsewhere in the Caribbean, rum is king on Martinique, and a visit to the historic distillery Habitation Clément offers a glimpse into the history and tradition of the islands’ favorite potent potable.

How to Get There: American Airlines flies to Martinique with stops at either New York’s JFK or Miami.

Photo by Aruba Tourism Authority


They call it the Aruba Effect: the feeling travelers experience when they head to the destination dubbed One Happy Island. Marketing speak aside, it’s pretty much impossible not to feel a sense of calm wash over you as you take in the breathtaking ocean views, pristine white beaches, and blue skies showcased vibrantly across this 70-square-mile isle. Although a constituent country of the Netherlands, Aruba is rich in history and cultural influences, and with more than 90 nationalities residing here, diversity reigns supreme when it comes to dining and experiences.

Where to Stay: It’s basically two for the price of one when you stay at Divi Aruba or Tamarijn Aruba All Inclusives, since guests can take advantage of amenities at both hotels conveniently located next to each other on Druif Beach. That includes access to 10 dining spots, eight bars, four freshwater pools, a state-of-the-art fitness and watersports
center, evening entertainment, and more.

Best Beaches: Whether you prefer privacy, meeting new people, or simply hanging with your multi-gen crew, there’s a stretch of sand for you. Palm Beach is known for its buzzing nightlife nearby, while Boca Catalina is perfect for those seeking seclusion. The aptly named Baby Beach, meanwhile, is ideal for families with small kids, and Eagle Beach is the country’s widest and most well known.

Top Tables: You’re in Aruba—it only makes sense to dine beachfront. You can’t get much closer to the seafood on your plate than at Flying Fishbone, where tables are placed on the sand and in the ocean. Meanwhile, at Fusion Restaurant Wine & Piano Bar, you’ll find a tapas-heavy menu with international flair, an extensive wine list, and live entertainment every night.

One-of-a-Kind Adventures: Submarines, UTVs, and caves…oh my! Embark on both land and sea excursions with local guide De Palm Tours, or channel your inner equestrian with a horseback tour at the Gold Mine Ranch.

When the Sun Goes Down: Feeling lucky? Known affectionately as the “Las Vegas of the Caribbean,” Aruba has 12 casinos located throughout the island. The popular Alhambra Casino houses 22 dining and retail outlets, a spa and salon, and, of course, plenty of gaming options.

How to Get There: In just under five hours, you can head to your happy place via direct flights with Delta or JetBlue from Logan. -Stefanie Schwalb

Photo by David Santiago Garcia/Aurora Photos/Getty Images

Holbox, Mexico

This 26-mile island off the coast of Quintana Roo is what Tulum was 50 years ago, long before all the yoga bros with man buns and Instagram influencers in butt floss invaded. There isn’t much to Holbox, which is precisely the point: no paved roads, no cars (golf carts only), and a town square where none of the buildings exceeds six stories. What you do get, extending in either direction, are pristine, talcum-powder beaches overlooking pale, placid blue water, with palapas serving food and drink in the sand and a range of hotels arrayed across the street.

Hot Spots: Ser Casasandra is an art hotel that boasts two of the island’s finest restaurants: Ser Esencia, which was lauded by the New York Times, and the toes-in-the-sand Mojito’s Beach Club, serving local and Cuban cuisine.

On the Water: Deep-sea fishing and other sports await, but a hammock suspended above the water is an equally popular activity.

Who You’ll Run Into: Nobody. Holbox has yet to catch on with the Kardashians of the world, and that’s part of its charm.

Risks: Mosquitos are a fact of life on the island, but some heavy-duty bug spray will help keep them at bay. On the upside, the protected mangroves help prevent the build-up of sargassum seaweed that’s such a nuisance elsewhere on the Riviera Maya.

When the Sun Goes Down: From July through this month, enjoy the otherworldly experience of nighttime snorkeling in a bioluminescent bay with tour operators such as Holbox Travel and Holbox Island Tours. Maybe even spot a flamingo or two around the island, if you’re lucky.

How to Get There: Fly to Cancun, Mexico, and either charter a puddle-jumper or hire a car or shuttle to take you the two hours to the coastal town of Chiquila, where a 20-minute ferry ride brings you to paradise.

Photo by Sylvain Sonnet/Getty Images

Eleuthera and Harbour Island, Bahamas

Love the idea of a winter escape to the Bahamas but not in the mood for the high-rise hubbub of Paradise Island? Pack your bags (and a good beach read) and jet off to Eleuthera. Known (if at all) for its natural wonders, watersports, and pineapples—there’s even a festival in June—the island is just over a mile wide and 110 miles long. Off the northern tip of Eleuthera is Harbour Island, a little-known bolthole for the rich and famous (likely due to its sprawling pink-sand beach).

Ritzy Nights: A former invitation-only beach club, the Dunmore on Harbour Island became a hotel in 2010—and is now one of the most whispered-about secrets in the Bahamas.

Must-Do: Mandatory excursions include a visit to the rock formation turned swimming pool known as the Queen’s Baths, a trip across the Glass Window Bridge (the narrowest point on the island), and a dip in one of the many saltwater cenotes, or blue holes, known mostly only to islanders.

Best Beaches: Alone in the sand on Harbour Island, a piece of driftwood known as the Lone Tree is one of the most Instagrammed spots in the Bahamas. We defy you to resist the temptation.

Top Tables: For a romantic dinner on Harbour Island, try Malcolm 51 at the Pink Sands resort for local specialties like stone-crab salad and native grouper, while Harry O’s, on the grittier side of town, has equally excellent local food and gorgeous views of the sunset.

Rainy-Day Excursion: Dunmore Town is a well-worn, slightly ramshackle collection of candy-colored cottages and quirky shops, including Eva’s Gift Straw Works for handmade goods and the Sugar Mill, the home-goods store of famed interior designer and local resident India Hicks (a goddaughter to King Charles).

How to Get There: Fly to Miami and catch American Airlines’ daily flight to Eleuthera, or fly to Atlanta to hop on one of Delta’s flights, offered five days a week.

Photo by Derek Galon/Getty Images


Gorgeously manicured beach resorts are nice, but sometimes, you just want to see nature in its natural form. Dominica’s 290 square miles represent exactly that, with volcanoes (including one of the world’s two “boiling lakes”), waterfalls, coral reefs, untouched rainforest, and both black- and white-sand beaches. The Waitukubuli National Trail, the Caribbean’s first long-distance hiking trail, spans its entire length, making it an ideal destination for rugged nature lovers.

Vibe: With no mega-resorts, the island’s accommodations are cottages, villas, and guesthouses, lending it an extremely chill and decidedly untouristy vibe.

Who You’ll Run Into: Iconoclasts, naturalists, and outdoorsy types who want to avoid the hordes disgorged by cruise ships on other islands.

Photo via Chelmicky/Getty Images

One-of-a-Kind Adventure: Experience the island’s geothermal liveliness by snorkeling off Champagne Reef or visiting Bubble Beach Spa in Soufrière, where rocks and boulders have been used to fashion natural hot tubs.

What to Avoid: It may be tempting to explore the volcanic craters, but be forewarned: The water is boiling, and the toxic fumes are dangerous.

Family Excursion: Jacko Steps is a gorgeous hike to a river where escaped slaves found refuge, offering a powerful and profound reminder of the Caribbean’s dark history of slavery.

Top Tables: It may look like just another beach bar, but Poz Restaurant and Bar serves some of the best Creole cooking on the island, and Poz himself is a local legend.

How to Get There: After a quick stopover in Puerto Rico through JetBlue, Delta, or United, you’ll land just an hour from the city center on the north side of the island.

Photo by Reinhard Dirscherl/Getty Images

Photo via CDWheatley/Getty Images

St. Croix

Nothing against the freneticism of St. Thomas or St. John’s photogenic ennui. But of the three U.S. Virgin Islands, only St. Croix (rhymes with joy) forges a Goldilocks-esque compromise between chill-deficient joiner-ism and sedentary bliss. Browse boutiques you’ve never heard of in Christiansted, with its shabby-chic Danish architecture and manageable size—like two Bay Villages. Plunge into a crystal-blue sea with so many explorable sunken ships they’re divvied up as Deep Wrecks vs. Shallow Wrecks. Trek to the heart of a rainforest and eat a six-course farm-to-table meal under the stars at the Ridge to Reef Farm. Or plop your derrière into a chair on a powdery beach for some “just right” one-on-one with the inner eyelids.

Cozy Nights: Family-friendly meets upscale at the Buccaneer Beach & Golf Resort, but for a kid-free getaway, we prefer the Fred, a 22-room boutique gem with a modern sensibility—and proximity to Frederiksted’s superior beaches.

Best Beaches: If you like your water blue and Jolly Rancher translucent, check out Sandy Point National Wildlife Refuge, so unspoiled it starred as the final scene of The Shawshank Redemption. Prefer amenities? Rainbow Beach, a few miles up the coast, offers terrific bar food, balanced cocktails, watersports, reggae, rentable chairs/umbrellas, and similar cerulean surf.

Top Tables: We’re currently crushing on the fiery Thai curries at Galangal, paired with grand-cru Rieslings hand-picked by its wine-guru owners; the spruced-up comfort food by husband-and-wife chef team Ryan and Michelle Bennett at Stones Throw; and Duggan’s Reef, where Wellesley expat Frank Duggan has presided over the island’s best steak and lobster since 1983, with a décor you might call Sports Pennants from Literally Every Bay State College.

Who You’ll Run Into: Recent sightings include Hugh Jackman honing his archery skills at Mount Victory Camp; Martha Stewart posing with charcoal-burnished birds on rotating spits behind La Reine Chicken Shack; and President Joe Biden golfing at the Buccaneer.

What to Avoid: Unintentional rudeness. Every interaction, be it paying for groceries or ordering a round, begins with “good morning,” “good afternoon,” or “good night” (as a greeting). It’s the “Simon Says” for not getting pegged as an Ugly Mainlander.

How to Get There: There are 20-minute seaplane rides from (also: to!) St. Thomas, but the route from Boston requires a flight through Miami, San Juan, or Fort Lauderdale. Not recommended: pirate ship (see intro). –Jolyon Helterman

Photo by Roy Conchie/Alamy Stock Photo


The easternmost island in the Caribbean, Barbados has a distinctly British flavor thanks to 400 years of English control (it broke its relationship with the British monarchy to become a republic in 2021). Still, there’s a vibrant local culture that’s uniquely “Bajan” (as the locals refer to themselves), and given its size, there’s something for everyone, including the Caribbean’s best surfing on the rougher eastern shore and the expansive, mellow beaches on the west coast. The island’s main industry is tourism, but there’s a non-mercenary genuineness to the islanders’ friendliness, which, along with the palm trees and trade winds, has made it a favorite among Caribbean cognoscenti.

Comfy Nights: Barbados caters to a broad demographic, boasting hotels and resorts that range from ultra-luxurious five-star hotels like Sandy Lane and the Coral Reef Club to more-affordable options like the Hilton and Butterfly Beach.

Who You’ll Bump Into: Visitors of note include most of the British royal family, music icons such as Elton John and Wyclef Jean, stars ranging from Michael Caine to Oprah Winfrey, and such celestial bodies as Venus and Serena Williams. But the island’s undisputed queen is Rihanna, who grew up there.

Family Excursions: Children will adore a visit to the Barbados Wildlife Reserve to see and feed the island’s famous green monkeys. The Nidhe Israel Synagogue in Bridgetown, built in 1654, is one of the oldest in the Americas, and the surrounding UNESCO World Heritage site is a treasure trove for history buffs.

One-of-a-Kind Adventure: Barbados boasts some of the world’s shallowest shipwrecks, perfect for snorkeling, and the local turtle population is so robust you’re almost guaranteed to see them.

Risks: Robberies and petty theft are not unheard of in Bridgetown. Leave your valuables in the hotel safe.

How to Get There: JetBlue flies nonstop from Logan to Grantley Adams International Airport.

First published in the print edition of the January 2023 issue, with the headline “What Are You Still Doing in Boston?!?!?”