How To Choose A Caribbean Island – Lonely Planet

Caribbean Caribbean 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 Caribbean 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, so if your time is short you can prioritize beach time over airport time.

Aruba’s beaches are lined with world-class resorts © Ultima Gaina / Getty Images

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 

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.  

Highlights: Harbour Island, Blue Holes National Park 

Cayman Caribbean 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.

Highlights: USS Kittiwake, Seven Mile Beach 

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.

Highlights: Santo Domingo’s Zona Colonial, Cascada El Limón

Jamaican beaches serve up some of the best sunsets © Getty Images


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 lurid and a distinct urban culture.

Highlights: Blue Mountain Peak, Blue Lagoon 

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. 

Highlights: Old San Juan, El Yunque National Forest

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.

Highlights: Îlet Pinel, Marigot Market 

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.

Highlights: Virgin Islands National Park, St John’s North Shore 

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

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.

Highlight: Shoal Bay East, Sandy Island 


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. 

Highlight: Bridgetown, Rockley Beach 


Best Caribbean island for divers, budget Caribbean 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

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

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.

Highlights: Playa Portomari, Christoffel National Park 

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


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.

Highlights: Ti Tou Gorge, Trafalgar Falls 


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 

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


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.

Highlights: La Soufrière, Réserve Cousteau


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.

Highlights: Citadelle Laferrière, Bassin Bleu 


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.

Highlights: Grande Anse des Salines, Route de la Trace 

St Kitts

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.

Highlights: Basseterre, Brimstone Hill Fortress National Park 

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.

Highlights: Anse Chastanet, The Pitons 

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.

Highlights: Pigeon Point, Corbin Local Wildlife Park 

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.

Highlights: Grace Bay Beach, Chalk Sound National Park 

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This article was originally published in March 2015 and updated June 2021.

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