How to choose a Caribbean island

The dozens of islands scattered across the Caribbean are a remarkably diverse lot. Pulsing Jamaica has little in common with group-filled 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 to choose? Big or little, near or far, urban or lost are among the many considerations that can turn choosing 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, so if your time is short you can prioritize beach time over airport time.

Each Caribbean Island offers something completely unique © Anna Jedynak/ Shutterstock

Easy access (multiple direct flights from US and Canada)

Aruba

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 familiar restaurants and bars.

Best for: Holidays requiring no thinking at all
Highlight: Natural Pool

The Bahamas

Offering the myriad choices of the Caribbean in a microcosm close to the US, the 700 islands of the Bahamas have far-flung hideaways and glossy mega-resorts.

Best for: Island-hopping explorers, divers, partiers, Americans needing a quick escape
Highlight: Harbour Island

Cayman Islands

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 for: Hassle-free holidays in what might seem like the 51st state, watersports
Highlight: USS Kittiwake

Dominican Republic

A large country with a dominant Hispanic culture, DR (as it’s called) has world-class resorts on fine beaches, lots of colonial-era history and untrammeled inland areas with forbidding peaks.

Best for: Resort-seekers, adventurers
Highlight: Santo Domingo’s Zona Colonial

The island of Jamaica offers a heady cultural cocktail © Rawpixel / Getty Images

Jamaica

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 lurid and a distinct urban culture.

Best for: Spicy food, spicy music, resort holidays, urban and natural adventures, quick trips from the US
Highlight: Blue Mountain Peak

Puerto Rico

Old San Juan is one of the great highlights of the region, a sprawling colonial throw-back that buzzes with a lively vibe. Big beach resorts, casinos, tangible history and rich Hispanic culture are the highlights.

Best for: Explorations beyond sun, sand and sea, not leaving the US
Highlight: El Yunque National Forest

St-Martin/Sint Maarten

Two distinct cultures, Dutch and French, share space on this smallish and 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.

Best for: Midrange-hotel holidays, daytrips into France, the Netherlands and the heart of Creole culture, the wildest airport bar on Earth
Highlight: Îlet Pinel

US Virgin Islands

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.

Best for: Americans who don’t have passports, mega-resort-lovers, nature-lovers
Highlight: Virgin Islands National Park

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

Farther afield (requiring a transfer or less frequent direct flights)

Anguilla

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 for: Luxurious but low-key holidays, isolation
Highlight: Shoal Bay East

Antigua

Lots of little beaches ringing this medium-sized island are lined with resorts large and small, modest and lavish. English Harbour offers yachtie hijinks and diverting colonial heritage.

Best for: Resort holidays with a couple of day trips
Highlight: Half Moon Bay

Barbados

British accents are common on this tidy, medium-sized island right on the edge of the Atlantic. Various beaches ideal for surfers, wind-surfers, budget sunbathers and traditional types who dress for dinner ring a truly welcoming island. Like some other ex-British colonial islands such as Antigua, Barbados has non-stop services from London in high season.

Best for: Any budget, activities, people who pack linen suits
Highlight: Bridgetown

Bonaire

One of the most interesting islands in the southern Caribbean, tiny Bonaire is justly famous for its spectacular diving right offshore. It also has a fascinating history and a winning and walkable main city of Kralendijk.

Best for: Divers, budget travelers, people who like to explore but don’t want a lot to explore
Highlight: Lac Bay

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

British Virgin Islands

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.

Best for: Divers and snorkelers, sunset cocktail parties, people who prefer the motion of the ocean
Highlight: The Baths

Cuba

Weirdly, wildly wonderful: a time-capsule of a vanished Caribbean on a huge island unlike any other. Cuba offers famous music, political challenges and disintegrating urban beauty. Havana alone is worth days of exploration amidst a paucity of frills. Watch for new flights as travel restrictions ease.

Best for: Reasonably priced holidays in a truly ‘foreign’ country, adventurers and explorers, bragging rights
Highlight: Viñales Valley

Curaçao

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

Best for: Off-the-beaten track wanderings, urban rambles
Highlight: Playa Portomari

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

Dominica

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 for: Climbers and trekkers, nature-lovers, people who want an escape from Caribbean clichés
Highlight: Ti Tou Gorge

Grenada

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.

Best for: Low-key holidays in beautiful natural surroundings, mixing with genial locals
Highlight: Underwater Sculpture Park

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

Guadeloupe

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 for: A topless day in the sun followed by a splendid seafood dinner
Highlight: La Soufrière

Haiti

Haiti offers the opposite of a care-free holiday. Challenges abound on this impoverished island that has suffered through natural disasters, but if you want to explore a rich culture that is the region’s most African, Haiti is for you. Recent improvements at the Cap-Haïtien airport include flights from Miami now serving Haiti’s north coast.

Best for: People who travel to learn and explore
Highlight: Citadelle Laferrière

Martinique

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 for: French-speakers, beautiful and isolated beaches, nature hikes
Highlight: Grande Anse des Salines

St Kitts

Paired with Nevis, St Kitts has big hotels and booming condo developments. It’s just large enough for a fun daytrip around the island that includes the vast pirate-era Brimstone Hill Fortress.

Best for: Comfortable holidays, daytrips to Nevis, talking like a pirate
Highlight: Basseterre

St Lucia

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.

Best for: Divers, snorkelers, trekkers, kite-surfers and more, nature-lovers, luxury seekers
Highlight: Anse Chastanet

St Vincent & the Grenadines

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.

Best for: Boaters, divers, explorers, people without schedules
Highlight: Tobago Cays

Trinidad

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.

Best for: An annual party to rival Rio’s
Highlight: Maracas Bay

Tobago

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.

Best for: Trad beach holidays without any buzz, diving, bird-watching
Highlight: Pigeon Point

Turks & Caicos

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.

Best for: Divers, boaters, beachcombers, lovers of mellow retreats on the sand
Highlight: Grace Bay Beach

Originally published March 2015. Updated November 2018.