Caribbean destinations this winter: a guide to finding your idea of paradise

Two lounge chairs with sun umbrella on a beach
Not all Caribbean beaches are the same, here's a guide to finding the right one for you © Anton Gvozdikov / Shutterstock

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.

A wave splashes against the rocks shielding the natural pool (Conchi), a popular tourist attraction, in Aruba
Aruba's beaches are lined with world-class resorts © Ultima Gaina / Getty Images

Best Caribbean islands with multiple direct flights from the US & Canada 

Aruba

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.

Introducing The Bahamas

The Bahamas

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.  

Scuba diving off the Cayman Islands coast, a great destination for underwater exploration
Scuba diving off the Cayman Islands coast, a great destination for underwater exploration © Stephen Frink / Getty Images

Cayman Islands

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.

Introducing the Dominican Republic

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.

A hammock swings in the wind as the sun sets on a Jamaican beach
Jamaican beaches serve up some of the best sunsets © Getty Images

Jamaica

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.

Just back from: Puerto Rico

Puerto Rico

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. 

An airplane lands at Princess Juliana International Airport (PJIA) at sunset on St. Maarten
An airplane lands over the accessible Maho Beach, Sint Maarten © Alain M. Duzant / 500px

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.

Trunk Bay, St John, United States Virgin Islands
Trunk Bay, St John, United States Virgin Islands © SeanPavonePhoto / Getty Images

US Virgin Islands

Best Caribbean islands for Americans who don't have passports, mega-resort-lovers, nature-lovers

The first Caribbean stop for many Americans has all the comforts - and familiar names - of home. St Thomas is commercial but St John and St Croix offer more natural and cultural allures.

Anguilla boasts some of the best beaches in the Caribbean © Shalamov / Getty Images
Anguilla boasts some of the best beaches in the Caribbean © Shalamov / Getty Images

Caribbean islands that are harder to get to 

Anguilla

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.

Chillin' in Antigua

Antigua

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
Barman lining up cocktails at Mullins Beach Bar, Barbados
Barman lining up cocktails at Mullins Beach Bar, Barbados © Justin Foulkes / Lonely Planet

Barbados

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. 

Bonaire

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 
The British Virgin Islands are a true yachtie's paradise © Cdwheatley / Getty Images
The British Virgin Islands are a true yachtie's paradise © Cdwheatley / Getty Images

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.

Cuba

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

Curaçao

Best Caribbean island for off-the-beaten-track wanderings, urban rambles

A medium-sized island with a focus beyond tourism. The main city of Willemstad has a famous, beautiful and historic harbor. Isolated beaches scattered about offer a few watery pleasures.

The picturesque village of Scotts Head, Dominica © htomas / Getty Images
The picturesque village of Scotts Head, Dominica © htomas / Getty Images

Dominica

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.

Martinique

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.

Just back from: tasting rum in Grenada

Grenada

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.

Guadeloupe packs a lot of attractions into a small area © Bennymarty / Getty Images
Guadeloupe packs a lot of attractions into a small area © Bennymarty / Getty Images

Guadeloupe

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.

Haiti

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.

The spectacular setting of Marigot Bay, St Lucia © Wildroze / Getty Images
The spectacular setting of Marigot Bay, Saint Lucia © Wildroze / Getty Images

Saint Lucia

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 

Trinidad

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 

Tobago

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.

Small islets and sublime water make Turks and Caicos perfect for island-hopping © Paula Anddrade / Getty Images
Small islets and sublime water make Turks and Caicos perfect for island-hopping © Paula Anddrade / Getty Images

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.

The best of Caribbean islands
This article was first published on May 14, 2019 and updated on November 3, 2021

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