We tend to talk about the Caribbean like it’s one big white-sand island. But the archipelago is made up of more than 7,000 islands that draw an arc through the Caribbean Sea, from just south of Florida to the coast of Venezuela. Though some 90 percent are uninhabited, dozens are full of life and open to tourism, each with its own personality.
Caribbean tourism officially represents 30 islands, from Anguilla to the US Virgin Islands. Any of these destinations would make a fine, if not fantastic, choice for any traveler who loves the tropics. But the ideal Caribbean vacation is about more than just a pretty beach. For those who don’t know Dominica from the Dominican Republic, here’s which island is right for you.
For seafoodies: Anguilla
Jamaica is the obvious choice for food-focused travelers. Jamaican jerk and Red Stripe beer have become icons of Caribbean cuisine, despite the variety of flavors found around the islands. Where Anguilla gets the advantage is the restaurant scene, which is famously dense with both the finest dining and deliciously casual eats.
Anguillan cuisine hinges on seafood, from prawns and spiny lobster to mahi-mahi and marlin. Like in Jamaica, salt cod is a staple of the Anguillan diet. Restaurants come in a wide range: Snack shacks in Rendezvous Bay serve whole snapper with a side of reggae. Beach bars in Sandy Ground fry up conch fritters, and maybe host DJs later on. For an especially memorable meal, and bill, treat yourself to Hibernia Restaurant and Art Gallery on the island’s quieter east side for French-Asian fusion with a Caribbean touch.
For the rum: Barbados
Barbados is the rum destination — and not just in the Caribbean. The world’s oldest rum distillery, Mount Gay, has been operating on Barbados since 1703. There are now three major rum distilleries on the island, which visitors can tour, as well as rum shops like Hercules and Braddies where tourists can not only stock up on bottles but also sip rum punch, grab some pub grub, and mingle with Bajans. There’s even a rum train, operated by the St. Nicholas Abbey Great House Plantation and Distillery. For a totally rum-focused holiday, plan your trip around the Barbados Food and Rum Festival in October.
For outdoor adventure: Dominican Republic
Resorts like Punta Cana and La Romana saddled the Dominican Republic with an “all-inclusive” reputation. While it is a fun, affordable place to sip cocktails poolside all day, a natural playground also awaits outside the Dominican Republic’s resort walls.
Beyond the 800-mile coastline, mountains tower at over 10,000 feet, waterfalls cascade into jungles, and sand dunes rise over patches of desert. Spend your days exploring Los Haitises National Park to see mangrove forests and petroglyphs, or stick to the coast at Jaragua National Park. Steer clear of the resort crowds on the Samaná Peninsula, best seen by zip line. Snorkel with stingrays, swim with humpback whales, or check out legendary surf spot Encuentro near resort town Cabarete. Whatever your outdoor fancy, you’ll find it in the Dominican Republic.
For luxury: St. Vincent and the Grenadines
Several Caribbean islands cater to the ultra-rich. The jet set summer in St. Barts. Fine diners sate their expensive tastes in Anguilla. Yachters drift toward the British Virgin Islands, one of which Richard Branson owns. And celebrities, socialites, and wealthy travelers invariably rub elbows in St. Vincent and the Grenadines, a 32-island chain located in the Lesser Antilles.
Most of the Grenadines are uninhabited; others are merely exclusive. Mustique, in particular, attracts a who’s who of modern royals, from Prince William and Duchess Kate to Mick Jagger and Paul McCartney. Macaroni Beach, a perennial candidate for the Caribbean’s finest, has become a celebrity in its own right while, across the island, Basil’s Bar has become the place to see, be seen, and drink after a long beach day.
Mustique is no book-it-and-go destination, however. Visitors must register upon arrival and have proof of accommodation before even booking flights. For many, that means shelling out for the Cotton House boutique hotel. Meanwhile, billionaires are now escaping the millionaire crowd on another Grenadine, Canouan, where the Mandarin Oriental will run you four figures a night.
For budget travelers: Trinidad and Tobago
Trinidad and Tobago is generally affordable by Caribbean standards. It’s also a twofer, as budget travelers can easily ferry between both islands. Tobago, the smaller island, is what everyone pictures when they think Caribbean, with sugar-white beaches where leatherback turtles nest. Trinidad is the more cultural of the two. Street vendors in the Port of Spain peddle some of the Caribbean’s best soul food, and calypso music is always playing, reminding listeners that the steel drum was invented in Trinidad and Tobago.
Visit either island in February and revelry is guaranteed. It famously hosts one of the wildest Carnival parties, with what some have called the world’s greatest street parade taking over Port of Spain every year. On calmer days, both islands are also favored by birdwatchers, whose hobby just so happens to be free.
For late nights: Puerto Rico
Puerto Rico could be top of the list for any type of travel. Old San Juan was established in the 16th century, making it one of the oldest continuously inhabited colonial settlements in the Americas. Less than an hour east, El Yunque is the only rainforest in the US Forest System, as well as its most biodiverse. Then there are bioluminescent bays; the world’s best mofongo, Puerto Rico’s signature plantain dish; and nightlife that never sleeps.
San Juan is a nonstop party. It’s a city obsessed with salsa dancing, but it finds every excuse to stay up late, from techno clubs to late-night bars blasting reggaeton. Even Old San Juan skews young after dark, with overflow bar-goers taking over the cobblestone streets. Anyone can appreciate the scene, but for American travelers, it’s as stress-free as a Caribbean vacation gets. There’s no need to even dig out that passport.
For fewer crowds: Grenada
Grenada tends to get forgotten when travelers brainstorm Caribbean destinations. It’s a small island, located roughly 500 miles off the coast of Venezuela, but living proof of the adage “good things come in small packages.” Known as the Spice Island, Grenada is among the world’s most prolific nutmeg producers and also grows cinnamon, cloves, ginger, mace, and some seriously fresh produce. When you’re not relaxing on Grand Anse Beach, tour the Belmont Estate cocoa plantation or River Antoine Rum Distillery, operational since 1785. Then, when it’s time to get back in the water, don’t miss the 30-foot Annandale Falls.
For wellness: Turks and Caicos
As Caribbean travel goes, Turks and Caicos is convertible. You’ll find upmarket bungalows, budget inns, family-friendly resorts, and honeymoon-ready villas, plus every water sport under the sun and some of the Caribbean’s best dive sites.
One resort, COMO Parrot Cay, has also made Turks and Caicos the go-to island for wellness. Included at the resort is the COMO Shambhala Retreat, which helps guests unwind with everything from Ayurveda and Japanese baths to private yoga, pilates, and meditation sessions and at least six different types of massage.
Relaxing on a private island costs a pretty penny, but day passes are available for those willing to hop a boat taxi to Parrot Cay. For something more accessible, check out The Spa at The Palms or Spa Tropique at The Sands at Grace Bay near Providenciales. Get a salt scrub if you can to see what makes Turks and Caicos salt so special.
For scuba divers: Bonaire or Belize
Bonaire is the westernmost ABC Island, a trio of Dutch territories off the coast of Venezuela. Not much is happening on the island compared to Aruba or Curacao, but when it comes to undersea life, Bonaire is right up there with its neighbors, not to mention the best dive sites on Earth.
Divers have their pick of 80-plus sites in Bonaire National Marine Park, including Alice in Wonderland where the double reef system is clearly visible. As a rule, beginners should stick to the east side of the island while the west side is more challenging. More experienced divers can also explore the Hilma Hooker wreck at about 100 feet.
Belize belongs to mainland Central America, but its largest island, Ambergris Caye, is another Caribbean destination divers would be remiss to skip. Most divers already know this, having popularized Lighthouse Reef and 400-foot-deep Great Blue Hole decades ago.
Other divers set their sights on the Gladden Spit and Silk Cayes Marine Reserve off the coast of Placencia, where whale sharks can be spotted every spring. To mingle with the gentle giants, plan your trip around the full moon in March, April, May, or June.
For families: Curacao or the Bahamas
Families come in all sizes and age ranges, so it’s not always easy to plan a one-size-fits-all vacation. Curacao makes it easier by offering a little something for everyone. Willemstad is a colorful, cultural capital where Dutch influences mix with the island’s Jewish heritage and art galleries stand alongside late-night cocktail bars. Outside the city, hikers can head to Christoffel National Park, snorkelers can visit Little Curacao, and the whole family can rendezvous for a walk through the Hato Caves.
If you’re planning a trip around little ones, on the other hand, the Bahamas are parent-approved for a classic beach holiday. Paradise Island is a good place to start. There are a wealth of family-friendly resorts that take the guesswork out of finding ways to entertain the kids, whether that means visiting the Aquaventure water park or spending a day fishing.
For eco-travelers: Dominica
Dominica is a full-on nature immersion. Dive sites like Champagne Reef, where bubbles from an undersea hot spring create a carbonated effect in the water, harbor species like hawksbill turtles and eagle rays. Rainforest blankets the interior, hiding waterfalls and hot springs, less so volcanoes. Hikers can see a little, or a lot, of everything on the 115-mile Waitukubuli Trail, the first long-distance walking route in the Caribbean. A love of nature brings most travelers to Dominica, but it’s also eco-accommodations that respect the environment just as much. Try the 3 Rivers & Rosalie Forest Eco Lodge for a sustainable stay.
For music obsessives: Jamaica
Jamaica’s music culture is well established. If nothing else, almost everybody knows Bob Marley and reggae by extension. In 2018, even UNESCO recognized the genre’s significance in Jamaica and influence around the world, adding reggae to its Intangible Cultural Heritage list.
Music lovers can learn about this heritage at the Bob Marley Museum in Kingston, then day trip to Nine Mile to see the icon’s childhood home and resting place. Elsewhere, on the island’s western tip, Negril’s Bourbon Beach is a legendary music venue that hosts live acts, primarily reggae bands, nightly when it’s not throwing themed parties at Seven Mile Beach.
Reggae’s only the start of Jamaica’s music scene, however. Dancehall is just as influential today. An offshoot of reggae that went on to influence rap and hip-hop, dancehall is an upbeat, rhythmic genre whose lyrics shows off the Jamaican patois. For music-filled nights out, stick around Kingston long enough to find your favorite dancehall club.
For all-inclusives: Aruba
There are two types of all-inclusive travelers: Those who plant themselves on the beach from the minute they arrive and don’t budge until check-out, and those who like to dig deeper into a destination without worrying about the usual trip-planning stresses. Aruba caters to both.
Resorts of varying cost have been built up and down the island’s west side, largely clustering around the Palm and Eagle beaches. Arikok National Park sprawls across the east side, home to natural pools, hilltop vistas, and caves painted with Amerindian petroglyphs. Start there when you’re not busy enjoying your hotel’s amenities, then work in an ATV tour, catamaran excursion, and plenty of time among the Dutch colonials in capital city Oranjestad.
For couples: St. Lucia or Martinique
Neighboring islands St. Lucia and Martinique are two sides of the same romantic coin: They’re small, tucked away in the southeastern arc of the Lesser Antilles, and only see a fraction of the tourists that visit islands like the Bahamas.
St. Lucia is cool and casual yet effortlessly romantic. It’s best for those who want nature by day, luxury by night. Think summiting volcanic peaks for a bird’s-eye view of the nearby islands, then retreating to a boutique villa overlooking a banana plantation in Soufrière. Or kayaking around Marigot Bay before a splurgy seafood dinner at the iconic Coal Pot in the capital.
Martinique can feel busier than St. Lucia, but it’s no less dreamy. The capital city, Fort-de-France, can get crowded during the mid-December to mid-April high season, but the European-leaning crowd is pleasantly cosmopolitan, with many visiting by way of cruise or yacht. Outside the city, lovebirds have their pick of activities, from boating between quiet coves to strolling through botanical gardens or touring rum distilleries. Expect to have a love affair with Creole cuisine while you’re there.
For living history: Cuba
Cuba’s beaches are just as scenic as the next island’s, but of anywhere in the Caribbean, it might be the island most worth dedicating to its cities. Havana is frozen in time, with a UNESCO-listed historic center dating to 1519 that has some of the oldest architecture in the Americas. Cienfuegos, a city on the Caribbean coast, also has a World Heritage site for a city center, flaunting 19th-century structures from its days as a trading hub. And the entire 16th-century town of Trinidad, later a leader in the sugar industry, was inscribed in 1988.
Cuba’s revolutionary history is also on full display. Hikers can trek to Fidel Castro’s former house and headquarters in Gran Parque Nacional Sierra Maestra. The spirited university city of Santa Clara is one big homage to Che Guevara, and where he’s now buried. History buffs can even visit the notorious Bay of Pigs on the southern coast, where there’s now a national park.