The Perfect Caribbean Island for Every Traveler

“There is something fresh and crisp about the first hours of a Caribbean day, a happy anticipation that something is about to happen, maybe just up the street or around the next corner.” ― Hunter S. Thompson

The Caribbean is a chameleon of ever-changing hues. Within that sun-soaked constellation of atolls, cays, and archipelagos, you’ll find pulsing tropical metropolises, frozen-in-time fishing villages, and pockets devoid of any inhabitants save seabirds, turtles, or wild pigs. Sail from the coral shoals of the Bahamas in the east to the volcanic Antilles in the west to hear English and Spanish yield to French and Dutch, while cacti-strewn deserts morph into lush rainforests and even snow-capped mountains.

Some signature charms are universal throughout the Caribbean—turquoise water, paradisiacal beaches, warm joie-de-vivre—but each of the sea’s 13 countries boasts its own distinctive flavor and texture. Even if only separated by a short boat ride, every nation offers its own unique cuisine, scenery, and personality. 

The Caribbean’s dazzling diversity means travelers of all stripes can find exactly what they’re looking for in a vacation somewhere in these sultry Elysian Isles. Whether you seek a fun family vacation, rum-fueled revelry, or a sandy sanctuary to kick back and do nothing, there’s a sublime Caribbean island tailor-made for you. 

Aruba: The Island for Family Vacations

Aruba has long ranked as the most popular Caribbean destination for U.S. travelers—and for good reason. Flights from the East Coast are frequent, affordable, and quick (about four hours from New York or D.C.), and a bevy of renowned all-inclusive resorts—an excellent option for traveling with children—bejewel the island’s breezy coastline. While it’s tempting to spend your entire Aruban sojourn blissed out by the pool in a glittering beachside hotel like the Divi & Tamarijn All Inclusives or the Ritz Carlton Aruba, plenty of beautiful sightseeing, cultural treasures, and delicious eats beckon beyond the resorts.   

Arikok National Park, protected land comprising one-fifth of Aruba’s landmass, offers some of the best hiking trails in the Caribbean. After trekking among hectares of towering cacti—an arid enchanted forest teeming with birds and lizards—you can cool off at Dos Playas, a secluded and gloriously empty beach within the park. Ask the concierge at the Divi & Tamarijn Aruba All Inclusive, this author’s favored retreat in Aruba, to arrange guides and transportation to the park.

Aruba’s cultural wonders are worthy of the island’s natural splendor. Spend a morning meandering through the narrow streets of Oranjestad, a Dutch colonial port steeped in pirate lore and festooned with pastel-colored architecture. Later in the evening, tie one on at Apotek, a gorgeous speakeasy housed within a century-old Dutch apothecary. For a delicious meal that will delight children and adults alike, Willem’s Dutch Pancakes fries up delicious pannenkoek—Dutch crepes as big as pizza platters. Try a savory crepe topped with shrimp or cheese or a dessert version sweetened with Nutella and luscious tropical fruits. 

Jamaica: The Island for Partying

Jamaicans are perpetually either planning a party or recovering from one—or so goes an old chestnut. Whether we’re talking gourmet rum, stubby bottles of Red Stripe, or herbal refreshments, Jamaicans take to bacchanalian indulgences with gusto. Clogged with nightclubs, beach bars, and peripatetic vendors hawking shots of rum, Negril could well be ground zero for partying in Jamaica.

Rick’s Cafe, a Negril landmark since the ‘70s, treats patrons to live reggae, frosty buckets of beer, and oversized cocktails. If you’re not too many tiki drinks into the wind, strut over to the restaurant’s patio to plunge into the sea from a 40-ft. cliff—don’t worry, the adrenaline neutralizes the effects of the margaritas. For the truly adventurous, Hedonism II, a clothing-optional resort, caters to those keen on, as the name suggests, public hedonism. 

Turks & Caicos: The Island for Kicking Back

In sharp contrast to Jamaica’s charming chaos, Turks & Caicos specializes in lazy delights like long naps on the beach, afternoons of reading by the pool, and schedules filled with delicious nothing. While nearby islands like Puerto Rico and Cuba, blessed with rich volcanic soil, boomed as sugar and agricultural hubs, Turks & Caicos, little more than an array of large sand bars, remained ignored in the colonial scramble for the Caribbean. What Turks & Caicos lacks in large settlements, it makes up for in august scenery—white sand beaches buffeted by the tradewinds, crimson sunsets melting into azure waters, and wildlife like flamingos and brown pelicans. 

At Ocean Club Resorts, a heavenly oasis on Providenciales Island, the days drift by as serenely as a cool zephyr through the palm fronds. While you could be forgiven for whiling away the time in your elegant suite—sumptuously furnished with artwork, a full kitchen, and oceanside balconies—make time for activities like gourmet rum-tastings, sea kayaking, or dining at excellent restaurants like Opus and Cabana Grill.

Grace Bay, the main settlement on Providenciales, is little more than a village, but the town buzzes each Thursday evening during Fish Fry, an open-air fair of food, music, and crafts. Plan to spend an hour or two sampling Turks Islander delicacies like cracked conch, banana ice cream, and rum punch. After dinner, peruse the rows of crafts merchants. Towards the end of the night, the market transforms into a raucous festival, complete with Junkanoo bands, a dance floor, and a sizzling hot stage.  

Barbados: The Island for Gourmet Travel

While Barbados’ most far-reaching claim to fame might be in rearing Rhianna, the island deserves at least as much renown for its rich culinary traditions. Long a bustling Caribbean entrepot, Barbados is a melting pot of Africa, India, England, and East Asia—influences deliciously reflected in Bajan cuisine. If you’re in town on a Friday, head to Oisten’s Fish Fry to relish specialties like pickled pork, curries lashed with Scotch bonnet, and succulent mahi mahi, barracuda, and snapper—sparkling fresh fish marinated with ginger and allspice and charred above a roaring open flame. Snag an ice-cold Banks pilsner to wash down all that spicy goodness and then cop a squat at a plastic picnic table to listen to live calypso music.

Taboras Restaurant, on the property of the Fairmont Royal Pavilion, an elegant oceanside belle in St. James province, serves Bajan mainstays like fried flying fish and seafood curries as well as fusion plates like Italian crudo. While fine dining is all well and good, the most memorable bite in Barbados might be the fried fish sandwiches at Cuz’s Fish Stand—crispy filets of the day’s catch heaped with coleslaw and hits of Marie Sharp hot sauce. For the rum connoisseur, Mount Gay Distillery, the oldest rum distillery in the world, is akin to a candy store for adults. During the two-hour tour, guests sip on rare vintages and learn about the wonderful alchemy that renders sugarcane into that silky, dark ambrosia synonymous with the Caribbean. 

U.S. Virgin Islands: The Island for Nature Lovers

Flights to the U.S. Virgin Islands are under four hours from most East Coast cities, and, better yet, since the USVI is an American territory, you don’t need to bring your passport or endure the rigamarole of customs to visit.  In the 1950s, the Rockefeller family purchased most of the islands’ undeveloped land to place in a conservation trust. Happily, 60% of the USVI, an archipelago blanketed with rainforests and mountains, remains pristine parkland. A biodiversity hotspot, the islands are home to scores of endemic species—including riotously colorful birds found nowhere else in the world. Robust flora and fauna thrive beneath the waters, too, and the USVI has long been a coveted destination for SCUBA divers and snorkelers. 

While 50 cays and islands—many mere specks in the ocean—compose the USVI, the three main islands are St. John, St. Thomas, and St. Croix. The island of St. John boasts a system of hiking trails, taking visitors along sea cliffs and through untouched swaths of jungle, maintained by the U.S. National Parks Service. After a long hike, chill out for an afternoon at Oppenheimer Beach, a sandy stretch famous for solitude and beauty. 

St. Thomas’s ecological splendor is rivaled only by the island’s culinary verve. Scores of elite East Coast chefs spend the winters in the USVI, drawn by both the balmy weather and smorgasbord of delicious tropical ingredients. For a quintessentially Virgin Islander breakfast—replete with buttered Johnny Cakes, fried plantains, and spicy-sweet chili sauce—make a stop at Bumpas Sandwich Shop in St. Thomas. On the white tablecloth side of the dining spectrum, The Old Stone Farmhouse is a longtime favorite for steaks and Caribbean lobsters paired with fine wines and rum cocktails.

Johnny Motley has written for The Daily Beast, Matador Network, Cool Material, and more. He’s on Twitter @johnnymotley and Instagram @motjohnny.