10 Overlooked Caribbean Islands for Winter Escapes

Enjoy uncrowded beaches, quiet villas and a laid-back Caribbean lifestyle on Anegada, Saba, Montserrat and more.

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Photo By: Charles Carroll

Photo By: Discover Dominica Authority

Photo By: Golden Rock Inn

Photo By: Montserrat Tourism Division

Photo By: Mount Cinnamon Resort

Photo By: Guadeloupe Islands Tourist Board

Photo By: Thinkstock

Photo By: Adam Nowek, flickr

Photo By: The British Virgin Islands

Photo By: By Pascalou petit (Own work) [GFDL or CC BY-SA 3.0], via Wikimedia Commons

St. Vincent and The Grenadines

For those who have heard of this Caribbean nation, due south of St. Lucia and west of Barbados, it’s likely because of its yacht scene. The Grenadines comprise 32 islands, making them a favorite among the boat life set. Among the better-known inhabited islands there’s Mustique, a private island and celebrity and royal favorite. The Cotten House is among the limited lodging options. Join the crowd if you haven’t heard of Canouan, not private but an equally wealthy island that attracts the one percent to its one hotel, recently rebranded as a Mandarin Oriental. Petit St Vincent (pictured) is another private island entry, with all of 22 cottages, two restaurants and one spa. Bequia is huge compared to some of the other islands, encompassing seven square miles to earn the title of second largest. Here, the four-star Bequia Beach Hotel competes with the brand-new Liming Bequia that opened in November 2018. And we can’t overlook St. Vincent, the largest in the group, even though it’s usually overshadowed by The Grenadines. Despite being the largest, the island is all of 18-miles long and refreshingly uncrowded, perfect for hiking the dormant La Soufriere volcano, snorkeling among reefs and lounging on golden beaches.


British Commonwealth Dominica in the West Indies (not to be confused with the Dominican Republic), didn’t share some of the other islands’ luck in 2017. Dominica suffering a massive hit to its infrastructure and crops when Hurricane Maria barrelled through the Caribbean. The Nature Island has never been the kind of place populated with all-inclusives and umbrella-drink-sipping tourists. Instead, its quiet appeal has long been the island’s diving, snorkeling and undeveloped landscape, filled with hot springs, rainforests and hiking trails. Visitors can once again experience many of these aspects as Dominica rebounds. Post-hurricane, about 90 percent of its structures were damaged, but that’s starting to change. As of 2019 the five-star, eco-friendly Secret Bay has reopened, and now offers a new restaurant and spa. The historic Fort Young Hotel has also reopened in its centrally located spot along the ocean, and is known for its on-site dive center. New construction is happening too: Jungle Bay just debuted as a collection of eco-villas that will host yoga retreats and regular guests. Just be advised that it isn’t accepting bookings until June 2019.


Nevis enjoyed a brief period in the spotlight in the '90s, back when Princess Diana vacationed there with Prince William and Prince Harry, and then more recently as the birthplace and early formative grounds of Alexander Hamilton. (Thanks, Hamilton musical.) But generally, this is where celebrities and non-celebrities alike escape the crowds. Located in the West Indies, Nevis is the smaller of the St. Kitts and Nevis island nation, and often forgotten about, particularly as travelers flock to the brand-new Park Hyatt St. Kitts Christophe Harbour on St. Kitts. But it’s fair to say that Nevis has barely changed since the royal family’s visit, and the Four Seasons Resort Nevis where they stayed is still welcoming moneyed guests. The Golden Rock Inn is a more affordable option, and freshly renovated. Its 11 rooms (consisting of cottages and a converted sugar mill) are surrounded by lush foliage, which is reflective of the island itself.


Despite its French-sounding name, Montserrat is actually part of Britain. The United Nations World Tourism Organization listed Montserrat as one of the least visited countries in the world, making it the least visited island in the Caribbean. From a tourism perspective the island never rebounded from a devastating volcanic eruption in the '90s that wiped out a good part of the southern half containing the capital and airport. The most affected area is still restricted to tourists as part of an exclusion zone. But the capital has been relocated and the airport rebuilt in the unaffected and verdant north. Tourism has remained low since a 15-minute flight from Antigua is required to reach the 10-mile-long island. As a result, most visitors are day trippers, although those who wish to stay longer will find mostly villas and Tropical Mansion Suites, the only hotel. They’ll also find a Caribbean way of life that has long been lost on the more popular islands.


You may have heard Grenada referred to as the Spice Island, and you may be aware it’s in the West Indies. But beyond that? It is just as well that most people draw a blank. Because it would be a shame for hordes of tourists to descend upon Grenada’s almost too-pretty-to-be-real white-sand beaches and pristine blue waters. There has been an uptick in visitors ever since JetBlue made the island more accessible with direct flights from New York in 2017, but since Grenada is closer to Venezuela than Florida, it’s hopefully not in danger of becoming the next Bahamas. This allows those who have heard about its charms to peacefully enjoy the island’s uncrowded beaches, nutmeg plantations and renowned dive sites. The main town of St. George is home to a cruise port and Grand Anse Beach, both best appreciated on a non-cruise day. Nearby is Mount Cinnamon Resort (this is Spice Island after all), a popular boutique property on a hill overlooking Grand Anse Beach.


Guadeloupe is among the Caribbean islands under French control, though it lacks the popularity of St. Barths and St. Martin, French territories which were deeply impacted by Hurricane Maria in 2017. The hurricane mostly spared Gwada, the local name, comprised of Grande-Terre, Basse-Terre and even smaller islands off their coasts. The former is known for its white-sand beaches, sugar plantations and hotels and restaurants. La Toubana Hotel & Spa on Grande-Terre is one of Guadeloupe's best and coveted for its sea views. Basse-Terre is defined by its waterfalls, rainforest national park and Jacques Cousteau Underwater Reserve. In 2015, direct seasonal flights on Norwegian Air have made getting here from the U.S. more accessible, with current routes being offered from New York’s JFK and Ft. Lauderdale.


A speck in the Leeward Islands in between Anguilla and St. Kitts and Nevis, tiny Saba is a Dutch territory that rarely nets any headlines. That’s because the island is all of five miles, contains no beaches and isn't the most accessible, since it requires connecting through St. Maarten via ferry or puddle jumper (and yes, it’s a short runway). Once there, there’s one road that winds through hilly villages that are home to about 2,000 people, tops. But don’t worry about being bored if you like scuba diving, snorkeling and/or hiking. There's something for every type of traveler in Saba, from relaxing in a cottage or villa to venturing into nearby towns for charming bars, restaurants and shopping for Saba’s signature lace. Choose from a handful of hotels, like the locally-owned Cottage Club Hotel or Queen’s Gardens Resort & Spa, Saba’s only (compact) resort. But even here, tucked away in the mountains, it’s unlikely that you’ll have to elbow crowds in order to enjoy the pool, spa and full-service restaurant.

Harbour Island, Bahamas

Thanks to the popularity of Paradise and Grand Bahama Islands, it’s easy to forget that the Bahamas are actually comprised of more than 700(!) islands. True, most are uninhabited, but a good number of the inhabited islands are overlooked by tourists heading to the all-inclusive playgrounds. Harbour Island is among the overlooked set, likely because there are no direct flights from the mainland, nor are there any major chain hotels on a sliver of land that’s all of three miles long. Yet these reasons prevent visitor overload, allowing those in on the secret to enjoy its famous pink sand beaches, local (if pricey) food scene and upmarket boutique hotels. New hotel openings aren’t as frequent here, making the recent addition of high-end Bahama House from adventure company Eleven Experience that more notable. Bikes, scooters and golf carts are the method of choice for rotating between the island’s offerings, proving that all-inclusives aren’t the only way to achieve a stress-free beach vacation.

British Virgin Islands

While the British Virgin Islands aren’t as overlooked as some other Caribbean islands, it’s also fair to say that most people would be hard pressed to name more than one or two, and as a whole they don’t enjoy the popularity of the U.S. Virgin Islands. This was the case even before Hurricanes Irma and Maria did a number on all but Anegada, which sustained minimal damage. Yet the islands have quickly rebounded, and as of winter 2019 many of the most popular restaurants and hotels have reopened. Comprised of 60 islands, most of which are uninhabited, Tortola and Virgin Gorda are among the most popular. On the latter, the iconic Bitter End Yacht Club hopes to reopen sometime in 2019. Not as well known to Americans is Anegada, which historically has attracted far fewer tourists to its uncrowded beaches and undeveloped landscape. The Anegada Beach Club is the place to stay here, and reopened soon after the storms struck. As the smallest of the four main islands, four-mile-long Jost Van Dyke is home to famed (and reopened) Soggy Dollar Bar and the "original" Painkiller cocktail. (Charles Tobias trademarked a blend of Pusser’s Rum, coconut cream, pineapple and orange juices after stealing the true original and recreating it.) Note that the laidback Sandcastle Hotel on Jost Van Dyke remains closed as of this writing.


Throughout the years neighboring St. Lucia has attracted more Americans than Martinique due to easier access. But new direct flights from the East Coast on Norwegian Air eliminate excuses to visit this mountainous French territory. More developed than some of the other islands on this list, Martinique offers a welcome mix of outdoor activities (hiking, diving, an 18-hole golf course), rum distilleries (including a notable local art collection at Habitation Clément) and dreamy beaches. The island has also developed a reputation for its French-Creole and traditional French cuisine. You can even visit the childhood home of Empress Josephine (Napoleon’s first wife). Other fun facts? Paul Gauguin logged four months here, where he completed 17 works before later becoming more famous for his Tahitian paintings. As for lodging, options range from affordable villas to five-star hotels; Diamant les Bains, one of the oldest hotels on the island, is readying to reopen in 2019 following an extensive renovation.

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