Top 28 of Caribbean Islands – Welcome to the Caribbean Islands. From high mountain peaks to shimmering reefs. Spicy salsa rhythms to deep rolling reggae. Pirate hideouts to sugar-sand beaches. The Caribbean is dizzyingly diverse.
Top 28 of Caribbean Islands
Cruz Bay, US Virgin Islands
Nowhere embodies the territory’s vibe better than Cruz Bay, St John. As the gateway to Virgin Islands National Park, it has trails right from town that wind by shrub-nibbling wild donkeys and drop onto secluded beaches prime for snorkeling. All the activity can make a visitor thirsty. So it’s a good thing Cruz Bay knows how to host a happy hour. Hippies, sea captains, retirees and reggae devotees all clink glasses at daily parties that spill out into the street.
Historic Cockburn Town, Turks & Caicos
Look no further for the old Caribbean than Cockburn Town. The tiny national capital of the Turks and Caicos. Here brightly painted colonial buildings line the roads and life goes on at a wonderfully slow pace miles away from the resorts of Providenciales. Wander down Duke St and Front St and pass whitewashed stone walls. Traditional streetlamps and creaking old buildings, some of which have miraculously survived for over two centuries in this charming backwater.
Carnival, Trinidad & Tobago
Home to one of the world’s biggest and best Carnivals, Trinidad is party central. And its two days of festival fabulousness have inspired the most creative and dynamic music and dance culture in the Caribbean. Visit a panyard and let the rhythmic sweetness of steel pan vibrate through your body. Check out the fireworks and drama of a soca concert. Or, best of all, don a spangly, feathery masquerade band costume and learn to ‘wine your waist’ like the locals during the two-day street parade.
Island Hopping in St Vincent & the Grenadines
It’s heard in office cubicles the world over daily: ‘I’m chucking it all in and going to tramp around tropical islands!’ In a world of package tourism, huge cruise ships and mega-resorts, the very idea seems lost in another, simpler time. Until, that is, you reach the Grenadines. Starting with Bequia, multiple tiny islands stretch south, linked by regular ferries. Jump aboard or hitch a ride on a passing yacht to feel the wind in your face.
Most island-goers would consider huge careening jets and large tracts of concrete runway to be noisy eyesores. But not on St Martin/Sint Maarten. Clustered around Princess Juliana International Airport – the area’s transportation hub – you’ll find a handful of bumpin’ bars that cling to the sides of the runway while also abutting the turquoise waters. At Sunset Bar & Grill, arrival times are posted in chalk on a surfboard and aircraft landings are awaited with much anticipation.
Soufrière, St Lucia
Swim-up bars, lavish spas, infinity pools, gourmet restaurants… When it comes to upscale resorts, St Lucia is hard to beat and there’s something for everybody. Some venues are straight from the pages of a glossy magazine, with luxurious units that ooze style and class, such as Ladera, Hotel Chocolat and Jade Mountain, near Soufrière, while others specialize in all-inclusive packages. You don’t need to remortgage the house to stay in one of them; special rates can be found on the hotels’ websites or on booking sites.
Spellbinding Views, St Kitts & Nevis
Nevis is tailor-made for trading the beach lounger for the nature trail. Hit the higher ground on a ramble through luxuriant tropical forest, colorful gardens and cane fields clinging to the slopes of volcanic Mt Nevis. Walk through air perfumed by exotic flowers and along paths shaded by fruit-laden trees while keeping an eye out for the elusive vervet monkey. Panoramic views opening up between the foliage extend to other islands, including neighboring St Kitts, and will have you burning up the bytes in your digicam, fast.
It’s easy to dismiss St-Barthélemy as the Caribbean’s capital of jet-setterdom, but there’s so much more to this hilly island. Cradled within its craggy coves are small towns with stone walls that look as though they’ve been plucked directly from the French countryside. This counterpoint of cultures plays out in the local cuisine as well – scores of world-class restaurants dish out expertly crafted meals that meld the savoir faire and mastery of French cuisine with vivid bursts of bright island flavors.
Oranjestad Ruins, Sint Eustatius
The ruins scattered throughout Sint Eustatius’ capital and sole town, Oranjestad, are whispers of a forgotten age, when rum, gold and slaves moved around the world with great alacrity. Sint Eustatius’ naturally deep harbor was the doorway to the New World, and during its golden era there were over 25,000 inhabitants representing a diverse spread of cultures and religions. Today, all that’s left of this time are the stone skeletons of several imposing forts, mansions, a synagogue and a church.
Rising dramatically out of the ocean, tiny Saba’s volcanic peak can only be fully appreciated in person. Even the craftiest photographers can’t correctly capture its beauty, especially ethereal when the setting sun casts flickering shadows across the forested terrain. Sign up for a trek with Crocodile James and wend your way through fascinatingly different climate zones as you make your way from the crashing waves up into the lazy clouds. From the top, you can stare out over the island’s traditional gingerbread-trimmed, red-roofed white cottages in the valleys below.
Old San Juan, Puerto Rico
Even those limited to a quick visit find it easy to fall under the beguiling spell of the cobblestone streets, pastel painted colonial buildings and grand fortresses of Old San Juan. Atop the ramparts of El Morro, the allure of this place is evident in every direction – from the labyrinth of crooked lanes to the endless sparkle of the Atlantic. By day, lose yourself in historical stories of blood and drama; by night, tap in (and tap along) to the condensed cluster of bars and clubs constituting the neighborhood’s nightlife.
Fishing Villages, Martinique
The remedy to the often-rampant development that surrounds the busy Martinican capital of Fort-de-France can be found in its many charming fishing villages, where life goes on much as it always has and the tourist dollar has still not made much of an impact. Surrounded by majestic forested hillsides and framed by crescent sand beaches, there’s a particularly gorgeous string of these beauties on the island’s southwestern corner – don’t miss lovely Anse d’Arlet Bourg or stunning Grande Anse.
Treasure Beach, Jamaica
Down in Treasure Beach, miles from the urban chaos of Kingston, you’ll find a quiet stretch of sand where visitors, expats and Jamaican locals kick back every evening. Beers are passed around, reggae cracks over the air and a supreme sense of chilled-out-ed-ness – oh, let’s just say it: ‘irie’ – descends onto the crowd. Music, food, Red Stripe, smiles – it all comes together here to create the laid-back Jamaican scene that many travelers dream of. Come for a day, stay for a week.
Citadelle Laferrière, Haiti
In recent years Haiti has been slowly revealing itself as the Caribbean’s hidden tourist gem. International hotel chains are starting to catch on, but you can still beat the crowds. Reasons to go? How about the Citadelle Laferrière, the largest fort in the Americas, built on a mountaintop to hold 5000 soldiers and defend the world’s first black republic from French invasion. It’s one of the Caribbean’s most staggering World Heritage sites, and you’ll have it almost entirely to yourself.
This Basse-Terre village strikes just the right balance between working fishing port and sophisticated dining destination to keep its well-heeled visitors happy. The setting is like a colonial-era painting, with wooden houses lining the tidy sand beach and colorful fishing boats bobbing up and down in the turquoise waters. Only the odd yacht in the distance gives you any indication of the smart crowd that flocks to Deshaies for its great restaurants, lively bars and fabulous nearby beaches.
The Carenage, St George’s, Grenada
One of the prettiest waterfronts in the Caribbean. Tthis buzzing little horseshoeshaped harbor is the perfect place to get a flavor of Grenada. With bobbing boats, busy cafes and a sprinkling of shady spots where you can watch the world go by or admire the lineup of gorgeous old waterside buildings. Spreading up from the bay, the hillside hodgepodge of brightly colored rooftops and a glowering stone fort get a scenic backdrop courtesy of the green, misty peaks of the Grand Etang National Park.
Kitesurfing, Dominican Republic
Do your part for the environment: use wind-powered transportation. Year-round strong offshore breezes make Cabarete, on the north coast of the DR, one of the undisputed capitals for the burgeoning sport of kitesurfing. Harnessing the wind’s power to propel you over the choppy surface of the Atlantic isn’t like another day at the beach. It takes training and muscles. Not to mention faith, before you can try the moves of the pros from around the world who ply their trade here.
Wild Wonder, Dominica
Dominica is one of the least developed and most unusual islands in the region. Covered almost entirely by thick, virgin rainforest, it has a landscape quilted with innumerable shades of green. Stagger into beautiful scenes of misty waterfalls, chilly and boiling lakes, hot sulfur springs steaming through the earth. And valleys and gorges chiseled by time and the elements. It’s a natural mosaic that will tug mightily at the hearts of artists, wanderers, romantics and anyone with a green bent.
Colorful Willemstad feels like a city in the old country, albeit with sunny skies and Caribbean views. This cosmopolitan capital is a cultural treasure trove, complete with unique museums, street art and vibrant nightlife. On both sides of the Sint Annabaai shipping channel, the city streets are lined with Dutch-colonial architecture, here with a citrus-hued, tropical twist. The historic districts are being restored and re-energized, especially Pietermaai, now housing boutique hotels, fine restaurants and funky cafes.
Music & Culture, Havana, Cuba
Few come to Cuba without visiting Havana, a hauntingly romantic city, ridden with ambiguity and imbued with shabby magnificence. A stroll around the mildewed but atmospheric streets of Habana Vieja reveals rusting American Buicks. Kids playing stickball with rolled-up balls of plastic, and a mishmash of architecture that mir- rors the nation’s diverse history. Underlying it all is the musical soundtrack for which Cuba is famous: rumba, salsa, son, reggaeton and trova.
USS Kittiwake, Cayman Islands
Off the coast of Seven Mile Beach, the 250ft (76m) submarine USS Kittiwake has found her final resting place among the creatures of the sea. Sitting in 60ft of water, the former rescue sub was purposefully sunk to create an artificial reef and a fascinating dive site. The doors and windows were removed, allowing in light and making for easy exploration of the decks and interiors. In fact, when conditions are clear, even snorkelers and free divers can investigate the ship’s upper reaches, which are only about 15ft (5m) below the surface.
Tortola, British Virgin Islands
Endowed with steady trade winds, tame currents and hundreds of protected bays, the British Virgin Islands are a sailor’s fantasyland. Many visitors come expressly to hoist a jib and dawdle among the multiple isles, trying to determine which one serves the best rum-pineapple-and-coconut Painkiller. Tortola, known as the charter-boat capital of the world, is the launching pad, so it’s easy to get geared up. Don’t know how to sail? Learn on the job with a sailing school.
Shore Diving, Bonaire
Almost the entire coast of Bonaire is ringed by some of the healthiest coral reefs in the region. Sometimes it seems like half the population of the island are divers – and why shouldn’t they be? The Unesco-recognized shore reefs can be reached right off your room’s back deck at oodles of low-key diver-run hotels. All-you-can-breathe-in-a-week tank specials are common. Beyond the exquisite shore diving are more challenging sites for advanced divers.
Surfing the Soup, Barbados
Although long the haunt of surf-happy locals, only recently has Barbados’ eastside surf break, called the Soup Bowl, gone supernova. Sets travel thousands of miles across the rough Atlantic and form into huge waves that challenge the world’s best. From September to December, faces found in surfing magazines stare wistfully out to sea from the very mellow beach village of Bathsheba. A slight calming from Jan- uary to May brings out the hopefuls.
Hidden Coves, the Bahamas
With nearly 700 islands spread across 100,000 sq miles of ocean. The Bahamas has enough secluded beaches and tempting hidden coves for several lifetimes of exploration. Each island has its own character to suit a traveler’s mood. For ethereal rosy-hued sands, hit up Eleuthera and Harbour Island, where beaches are tinted pink by crushed coral. The 365 Exuma Cays are a wonderland of cerulean waters and uninhabited islets. While Grand Bahama offers luscious sands fringed by teem- ing reefs and steaming mangroves.
Hot & Sandy Aruba
Hit the beach with 10,000 of your new best friends on Aruba. Two legendary beaches, Eagle and Palm, stretch for miles and fulfill the sundrenched fantasies of shivering hordes every winter. Wide, white and powdery, they face water that has enough surf to be interesting but not so much you’ll be lost at sea. The beaches are backed by shady palms, and cheery holidaymakers stay at the long row of re- sorts just behind. The scene here is pulsing, vibrant and happy, with action that ex- tends well into the night.
English Harbour, Antigua
Antigua has been blessed with many off-the-charts splendors. Including gorgeous beaches, crystalline waters and a deeply indented coastline with natural harbors. There’s colonial tradition here too. English Harbour flaunts its heritage at one of the preeminent historic sites in the Caribbean: Nelson’s Dockyard. Travel back to the 18th century as you wander along cobbled lanes and past meticulously restored old buildings. Still a working marina, it’s also one of the world’s key yachting centers.
Beach Time, Anguilla
It’s hard to go past the spectacular white sandy coast and glistening turquoise wa- ters of Anguilla. The ultimate way to while away days under the bright tropical sun on the beach is lazing on sun loungers. Splashing in the sea and licking your fingers after gorging on ribs grilled over smoky barbecues. On weekends especially, find local artists jammin’ at their favorite seaside haunts. Such as the world famous Bankie Banx’s Dune Preserve, built from driftwood and old boats.