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)
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
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
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
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
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
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
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
- 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)
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
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
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
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
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
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
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
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
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 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
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
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
The spectacular setting of Marigot Bay, St Lucia © Wildroze / Getty Images
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
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
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
Small islets and sublime water make Turks and Caicos perfect for island-hopping © Paula Anddrade / Getty Images
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.