Is your desire for a rum punch rising just as temperatures are dropping? If so, now is the time to plan your annual getaway to the Caribbean. But while many travelers opt to return to the same place year after year — the migratory pattern of seasonal snowbirds markedly similar to the avian variety — why not consider branching out (pun intended) to a different tropical island? Change can be daunting, of course, which is why we’ve rounded up a wide selection of Caribbean islands to consider — based on your individual interests. Whether interested in deep sea fishing, fish fry dancing, night dives, or nightlife, read on for the best 17 Caribbean islands to visit this winter. Your very own highly-curated island in the sun awaits.
1. Nightlife: Antigua, Leeward Islands
(Image provided by Carlisle Bay)
Usually, to mingle with locals or make new friends, you must know someone at the destination before arriving. But this isn’t the case on the island of Antigua, where there is a party at Shirley Heights Lookout every Sunday from 4 pm until long after the sun goes down — the formal festivities conclude at 10 pm, but you can always expect some stragglers. Afterward, retreat to your private oasis on the sandy shores of Carlisle Bay, and recharge enough to head into English Harbour for some espresso martinis the next night. Retox to detox is a perfect mantra for a getaway on this uber-social Caribbean island.
2. Diving: Bonaire, Dutch Caribbean
(Image provided by Bonaire Tourism)
Bonaire is the least-touristed destination in the ABC Islands of the Dutch Caribbean and is perfect for the diving fanatic. Visitors can enjoy off-shore diving nearly everywhere on the island, protected by a natural marine park to ensure the kind of pristine underwater environment rarely seen outside the Galapagos — the coral reefs are teeming with schools of fish, turtles, and more. Harbour Village Bonaire sits on four acres of tropical paradise from the comfort of its exclusive beach and is renowned for its unique diving and snorkeling experiences. A personal diving concierge is provided for each guest to ensure safety and maximum enjoyment, and the PADI five-star dive center allows visitors of all ages to get lessons onsite. Additionally, birders will be in heaven at the Pekelmeer Flamingo Sanctuary. Bonaire's airport is named Flamingo for a reason — the pink bird is even the symbol on your passport stamp upon arrival.
3. Cuisine: Providenciales, The Turks & Caicos Islands
(Image provided by the Author)
Calling all foodies — if it’s a tropical ambiance, fresh seafood, and generous pours of rum that you’re after, head to the island of Providenciales on Turks & Caicos. Book a stay at the Grace Bay Club, overlooking Grace Bay Beach (consistently ranked as one of the most beautiful beaches in the world), and set out to sea on a sunset catamaran cruise. As for culinary delights, you truly can’t go wrong. But our personal favorites are Da Conch Shack, where you can dine with your feet in the sand as the waves crash on the shore, or Coco Bistro, a romantic hideaway set amongst the largest palm grove on the island.
4. Surfing: Barbados, Leeward Islands
(Image provided by Visit Barbados)
Due to its location on the farthest eastern point of the Caribbean island chain, Barbados is a surfer's paradise, with waves originating in South America and Africa crashing onto its shores. Sign up for a lesson at Burkie's Surf School taught by the first professional Bajan surfer, Alan Burke. And Barbados isn't just known for surfing but windsurfing and kite-surfing, as well — we suggest heading out to Silver Sands Beach. Negotiating your sail can be quite strenuous (particularly if you've been overserved the night before), but the famous adage proves true: The cure for everything is sweat, tears, or the sea. Hopefully, only two such elements will be required on your aquatic adventures. Not to worry — a sunset cocktail at The House Barbados is the perfect place to revive yourself after a strenuous day at sea.
5. Culture: Nassau, The Bahamas, British West Indies
(Image provided by the Author)
The flourishing Bahamian capital of Nassau is home to centuries of history that can be retraced in one of the most delectable ways — a food tour, of course. Tru Bahamian Food Tours traces the origin of Caribbean cuisine back to the roots of generations-old family recipes in West Africa. Afterward, find inspiration beachside in one of the colorful huts of Compass Point Beach Resort, where The Rolling Stones recorded in the 1970s.
6. Music: Jamaica, Western Caribbean
(Image provided by the Author)
Music lovers needn't look further than the legendary island of Jamaica, the creative homeland of dance hall beats, reggae, and — of course — the iconic Bob Marley. And you will hear local artists performing the streets of Kingston to the shores of Montego Bay as steel drums accompany the settings of most Jamaican locales. Head to Strawberry Hill Hotel to stay in the Blue Mountains retreat frequented by Grace Jones, Willie Nelson, the Rolling Stones, and (of course) Bob Marley. For a taste of tropical elegance, head to Montego Bay and book a villa at Round Hill, the favored Caribbean Retreat of JFK and Jackie Kennedy — the crashing of the waves combines with the rhythm of the steel drums on the patio at dinnertime, creating a tropical vibe that's music to one's ears.
7. Hiking: Dominica, Windward Islands
(Image provided by Dominica Tourism)
Who says the Caribbean is all about sunbathing on the beach? With its Boiling Lakes, tropical rainforests, champagne reefs, and black-sand beaches, Dominica is known as the Nature Island of the Caribbean. Book a stay at the Fort Young Hotel in the island's capital of Roseau before embarking on some of the most challenging, exhilarating hikes in the tropics. The lush wildness of Dominica is enhanced by a thriving local indigenous culture, and a visit to the Kalinago Cultural Center in Bataka is a must-visit while on the island.
8. Sightseeing: Curacao, Dutch Caribbean
(Image provided by Curacao Tourism)
History lovers should explore the UNESCO World Heritage site, the capital city of Curacao, Willemstad. With its colorful buildings, Dutch colonial architecture, and floating markets of Venezuelan vendors, there's endless splendor to behold. Plus — unsurprisingly, given its location in the crystal-clear waters of the ABC islands — the island boasts endlessly fascinating dive sites (there's no shortage of ill-fated shipwrecks to explore) and an abundance of tropical fish and seahorses. Scuba experts and beginners should book a stay at LionsDive Beach Resort, where you can embark on your Dive SSI training in the most magnificent of surroundings and attain an open-water diving certificate in under a week. In the words of a popular local parlance — the native language of Papiamento — everything is dushi.
9. Shark Diving: Bimini, The Bahamas
(Image provided by the Author)
Located only 50 miles east of Miami, Bimini is the westernmost island chain in the Bahamas — and a truly remote idyll, whether you’re seeking solitude or adventure. For those living (or vacationing) for the thrill of it, reef shark diving in open water is available off the island’s sandy coasts. And while you’re out there exploring (and taking risks), sign up for The Bash, a lionfish-hunting excursion provided by the Woody Foundation, which raises money for victims of paralysis while cleansing the sea of invasive species.
10. Rum: Grenada, Windward Islands
(Image provided by the Mount Cinnamon Resort)
Grenada is a severely underrated Eastern Caribbean getaway located just outside the hurricane belt, making the island popular with under-the-radar billionaires parking their yachts in the off-season. But it won't be long before the rest of the world catches onto the charms of Grenada, as well. Stay at the luxurious Mount Cinnamon Resort overlooking the picture-perfect Grand Anse Beach, and hike to Fort Frederick to enjoy panoramic views of the island. Book a trip on a Carriacou sloop with Savvy Sailing — the owner, Danny Donelan, was instrumental in reviving the heritage of traditional Caribbean sailboats. (During your sail, snorkel to one of the underwater sculpture parks restoring the local reefs). Last but not least, the Spice Island of the Caribbean is famous for its rum. A trip to the historic River Antoine Estate Rum Distillery is mandatory for lovers of the tropical libation, where the alcohol is so potent it's illegal to take home on your flight.
11. Solitude: South Caicos, The Turks & Caicos Islands
(Image provided by Sailrock Resort)
If you’re in the mood for luxury, look no further than Turks & Caicos, and while Providenciales is definitely the best spot to party, travelers should book a connecting flight to South Caicos to experience the ultimate secluded paradise. Sailrock Resort offers private villas perfect for romantic getaways or friend and family vacations where the only unexpected disturbance is the occasional wild donkey strolling by your seaside pool.
12. Romance: St. Lucia, Windward Islands
(Image provided by the S. Lucia Tourism)
St. Lucia is famous in the Eastern Caribbean for its magnificent Piton mountains, glorious views, and even more glorious accommodations. The three-walled hotel room was invented in St. Lucia, so guests have the opportunity to look directly out to the Caribbean Sea from the comfort of their (mosquito-netted) beds. To enjoy these famed accommodations, book a stay at Ladera Resort or Jade Mountain. Chocolate lovers should make their own cocoa and enjoy a room overlooking the mountains at Rabot Hotel, while sun-seekers should book a cottage at Sugar Beach, which is nestled in a breathtaking location on the water between the twin peaks of the Piton mountain range.
13. Street Art: Aruba, Dutch Caribbean
(Image provided by Adobe Stock)
While the island of Aruba may be better known for its nightlife and white-sand beaches — there’s a reason the destination has one of the highest return rates in the Caribbean — the flourishing art scene of San Nicolas is lesser known to travelers. Visit the ArtisA Gallery and take a mural tour before retreating to your private casita in the palm tree-enclosed paradise of the Boardwalk Boutique Hotel.
14. Sailing: Bermuda, North Atlantic
(Image provided by Adobe Stock)
Though the British territory of Bermuda is not technically considered part of the Caribbean in terms of geography, when it comes to culture, ambiance, and pink-sand beaches, it’s undoubtedly the West Indies. Head to the island for the Newport Bermuda Race, an annual sailing event that turns out throngs of revelers and observers worldwide — though many are in town for the parties. Speaking of parties, the Cup Match weekend is another fabulous time to visit to witness another of the island’s favorite sporting pastimes: Cricket. And, if you want to be in the center of the action, book a stay at the legendary Hamilton Princess, a resort that’s as pink as the sands it sits upon.
15. Fishing: St. Thomas, The U.S. Virgin Islands
(Image provided by the Author)
St. Thomas is the most popular tourist destination in the U.S. Virgin Islands and offers an array of diverting nightlife activities, as well as glorious villas available for rent boasting sweeping views of the surrounding islands. But if you’re after the biggest (if not deadliest) catch, then head out onto the surrounding waters to fish Blackfin and Yellowfin Tuna, Blue Marlin, Wahoo, and Mahi-Mahi. Anglers from around the globe head to this island in the Virgin Islands archipelago for glory — St. Thomas is one of the best destinations for sportfishing in the world.
16. Sunbathing: Dominican Republic, Island of Hispaniola
(Image provided by Adobe Stock)
The Dominican Republic is part of the Island of Hispaniola, which shares a border with Haiti. While the capital of Santo Domingo is legendary for its culture and vibrant city life, Punta Cana — on the island’s eastern shore, where the Atlantic meets the Caribbean Sea — is famous for its beaches. If your idea of a tropical getaway is one that is all-inclusive, then book your flight to the Dominican Republic now. There’s no shortage of loungers (or rum punches) to keep you occupied as you while away your day in your own personal version of Jimmy Buffet’s Margaritaville. Cheers!
17. Nature: St. John, The U.S. Virgin Islands
(Image provided by Caneel Bay)
If it’s nature you’re after, St. John is heaven on earth (or heaven in the tropics). More than half of the island’s land is protected by the Virgin Islands National Park, and, as of this year, travelers now have the option to stay within the park at the recently-reopened Cinnamon Bay Beach & Campground, which is available for guests once more after hurricanes ravaged the coastline five years ago. Luckily, ‘America’s Paradise’ in the U.S. Virgin Islands remains glisteningly preserved — and now better than ever — thanks to conservation efforts on the island, and a stay at Cinnamon Bay should top every nature lover’s bucket list.
