Caribbean destinations this winter: a guide to finding your idea of paradise
The dozens of islands scattered across the Caribbean are a remarkably diverse lot. Pulsing Jamaica has little in common with low-key Aruba, and even islands in plain sight of each other like St Kitts and Nevis are vastly different not just in appearance but in what they offer visitors.
So for the Caribbean-bound visitor, which island among the many do you choose? Big or little, near or far, urban or rural are among the many considerations that can turn picking a carefree holiday into a perplexing chore.
Happily, our Caribbean islands primer can take the pain out of choosing what's right for you. We've got the low-down on all the most-visited islands, complete with what's best about each one, and we've categorized them by their ease of access, helping you to prioritize beach time over airport time.
Best Caribbean islands with multiple direct flights from the US & Canada
Best Caribbean island for holidays that require no thinking at all
Arid and nearly featureless, Aruba's main attraction is a ribbon of beaches lined with big world-class resorts and backed up with malls of local restaurants and bars.
- Highlights: Natural Pool, Arikok National Park
Best Caribbean island for island-hopping explorers, divers, partiers, Americans needing a quick escape
With more than 700 islands, the myriad of choices are endless when planning a trip to The Bahamas. Looking for far-flung hideaways or glossy mega-resorts, a lively party scene or outdoor excursions with the family, this Caribbean country has it all.
- Highlights: Harbour Island, Blue Holes National Park
Best Caribbean island for hassle-free holidays in what might seem like the 51st state, watersports
Grand Cayman is reminiscent of South Florida, only more orderly and with less traffic. It offers resorts of all stripes, tax shelters and famous diving, snorkeling and swimming with schools of stingrays.
Best Caribbean island for resort-seekers, adventurers
A large country with a dominant Hispanic culture, the DR (as it's called) has world-class resorts on fine beaches and untrammeled inland areas with forbidding peaks.
Best Caribbean island for spicy food, lively music, resort holidays, urban and natural adventures, quick trips from the US
Seemingly the center of Caribbean clichés such as Bob Marley songs played to the rhythm of opening beer bottles, vast Jamaica offers up resorts from posh to budget and a distinct urban culture.
Best Caribbean island for explorations beyond sun, sand and sea
Puerto Rico inspires Caribbean daydreams for good reason: it can satisfy both the lethargic beach bum and the budding big-wave surfer – all in a long weekend. If you don't want to spend all your time at the beach, head to the casinos or explore the tangible history and rich Hispanic culture of the island.
St-Martin & Sint Maarten
Best Caribbean island for midrange-hotel holidays, daytrips into France, the Netherlands and the heart of Creole culture
Two distinct cultures, Dutch and French, share space on this small, but very lively island. Like a brain these two hemispheres are greater in sum than in parts: the French offer holidays with reserve while the Dutch party down.
US Virgin Islands
Best Caribbean islands for Americans who don't have passports, mega-resort-lovers, nature-lovers
Caribbean islands that are harder to get to
Best Caribbean island for luxurious but low-key holidays, isolation
In a sea of beaches that set the standard for beachy clichés, the beaches on this tiny island are the definitive versions. Small, with an amiable local culture and luxurious villas scattered about.
Best Caribbean island for resort holidays with a couple of day trips
Many of Antigua's 365 beaches are lined with resorts large and small, modest and lavish. English Harbour offers yachtie hijinks and popular historic sites. The sister island of Barbuda is home to the fantastic Frigate Bird Sanctuary.
- Highlights: Half Moon Bay, Cades Reef
Best Caribbean island for any budget, activities, people who pack linen suits
A slew of beaches ideal for surfers, wind-surfers, budget sunbathers and traditional types who dress for dinner make Barbados a truly welcoming island. There's been a steady increase in nonstop flights to the country.
Best Caribbean island for divers, budget travelers, people who like to explore but don't want a lot to explore
One of the most interesting islands in the southern Caribbean, tiny Bonaire is famous for its spectacular diving right offshore. It also has a fascinating history and a winning and walkable main city of Kralendijk.
- Highlights: Lac Bay, South End
British Virgin Islands
Best Caribbean island for divers and snorkelers, sunset cocktail parties, people who prefer the motion of the ocean
The BVIs are a richer, less-developed and more isolated version of the US Virgin Islands. Yachties and divers find their bliss amongst the 40 islands here; the main island, Tortola, offers glam diversions.
- Highlights: The Baths, Cow Wreck Bay
Best Caribbean island for reasonably priced holidays, adventure and bragging rights
Cuba offers fantastic music, political challenges and stark natural beauty that's often overlooked. Havana alone is worth days of exploration amidst a paucity of frills. Watch for new flights as travel restrictions ease.
- Highlight: Viñales Valley, Malecón
Best Caribbean island for off-the-beaten-track wanderings, urban rambles
Best Caribbean island for hikers, nature-lovers, people who want an escape from island clichés
Lacking the plethora of beaches found elsewhere, Dominica is the region's unspoiled gem with peaks and valleys swathed in rain forest and accented by waterfalls.
Best Caribbean island for French-speakers, beautiful and isolated beaches, nature hikes
The most Gallic corner of the Caribbean has a sprawling main town of Fort-de-France and an untouristy focus. Far-flung beaches reward daytrippers.
Best Caribbean island for low-key holidays in beautiful natural surroundings
You really can smell nutmeg in the air of this small ex-British colony which has one of the region's most interesting capitals, St George's. Small and inviting beaches vie with rainforest-clad hills for attention.
- Highlights: Underwater Sculpture Park, Gouyave Nutmeg Processing Cooperative
Best Caribbean island for a topless day in the sun followed by a splendid seafood dinner
French-accented Guadeloupe offers relaxed islands for people who want to travel little, laze on the sand and enjoy especially good food. It packs great beaches and tropical nature in a small package.
Best Caribbean island for people who travel to learn and explore
Haiti offers tranquil beaches, tumbling waterfalls and awe-inspiring landscapes. The world’s only successful slave rebellion happened here, and the music, art and culture that came with it make Haiti entirely unique
Editor's note: Prior to traveling to Haiti, be sure to check the US State Department for updated travel advisories.
- Highlights: Citadelle Laferrière, Bassin Bleu
St Kitts & Nevis
Best Caribbean island for comfortable holidays, day trips to Nevis
Paired with Nevis, St Kitts has big hotels and booming condo developments. It's just large enough for a fun day trip around the island that includes the vast pirate-era Brimstone Hill Fortress.
Best Caribbean island for divers, snorkelers, trekkers, kite-surfers, nature-lovers, luxury seekers
Beaches, beautiful resorts, and lushly forested hills are the troika of lures on this island long popular with the French and honeymooners of all tongues. Activities abound in and out of the water.
St Vincent & the Grenadines
Best Caribbean island for boaters, divers, explorers, people without schedules
Catching rides on fishing boats between beach-ringed islands is the classic Grenadine experience (or charter your own boat). The main island, St Vincent, is mostly rainforest while little idyllic Bequia is the star of the oh-so-mellow Grenadines.
- Highlights: Tobago Cays, Mayreau
Best Caribbean island for an annual Carnival party to rival Rio's
Overshadowing neighboring Tobago, Trinidad is a big, pulsing Caribbean island that revels in Creole culture and boasts a party scene that peaks during one of the world's great Carnival celebrations.
- Highlight: Maracas Bay, Asa Wright Nature Centre
Best Caribbean island for quiet beach holidays without any buzz, diving, bird-watching
The pint-sized companion to Trinidad boasts everything the larger island lacks: pristine nature, resorts worth the trip and fun in and out of the water.
Turks & Caicos
Best Caribbean islands for divers, boaters, beachcombers, lovers of mellow retreats on the sand
Turks & Caicos consists of little islands with perfect beaches and the requisite turquoise waters beg for discovery. Nowhere here is very busy, even the world-class dive sites.
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