Let the island hopping begin.
The one-million-mile swath of the Caribbean Sea is home to 7,000 islands, only a handful of which are visited by the average traveler. Since seeing them all is a feat even the most swashbuckling of pirates couldn’t achieve, we’ve narrowed down the most bucket-list-worthy of the bunch. From the most popular sailing locales to some of the lesser-known dive spots, these island paradises are so stunningly perfect they’ve been stand-ins for deserted islands in blockbuster films. Now comes the tough part—which island to hop over to first.
Sunbathe in Anguilla
It’s not hard to find a spot to sit back and relax in Anguilla, the tiny British overseas territory north of St. Martin. The eel-shaped island (named after the French word, anguille) is lined with 33 white-sand beaches, many of which rank among the world’s 10 best. Bask on Shoal Bay Beach or Rendezvous Bay (also home to villas and day spas), or set off for somewhere less developed like Scrub Island, the largest of Anguilla’s six offshore cays– It’s so secluded you’ll feel as if you’re on your very own private island.
Go Hiking in Guadeloupe
Guadeloupe National Park on the island of Basse-Terre spans an impressive 54 acres of waterfalls and forests—plus it has the tallest peak in the Lesser Antilles, Soufrière volcano. Nearly 200 miles of trails twist through the practically untouched terrain. Start with one of the simpler hikes like the 10.5-mile Route de la Traversée. Take a detour along the way to the Cascade aux Écrevisses, aka Crayfish Waterfall, or cross the wooden footbridge over the Bras-David River on the Maison de la Forêt loop trail.
Sail in the Virgin Islands
The British Virgin Islands may hold the reputation as the “Sailing Capital of the Caribbean,” with the Sir Francis Drake Channel ensuring plenty of safe anchorages, but that doesn’t mean you should write off the U.S. Virgin Islands. Sailing is just as popular a pastime around the pristine island of St. John. Sail from either set exploring the hundred-plus untouched islands and secluded cays scattered within a 50-nautical-mile radius.
Snorkel in the Cayman Islands
There are plenty of snorkel sites in the Cayman Islands to spot colorful reefs and tropical fish. Put your mask and fins to use in the shallow waters of Grand Cayman’s popular Stingray City, or head to sea turtle-filled Spotts Beach (which doubles as a great place to catch the sunrise). At Seven Mile Beach’s Cemetery Beach, you’ll find one of the most colorful stretches of coral reef in Grand Cayman.
Shop in St. Thomas
Yes, Curaçao’s Willemstad and St. Maarten’s Philipsburg may be duty-free favorites. But for something that’s equal parts craft market and boutique shopping, make your way to Main Street in Charlotte Amalie, the capital of the USVI and a popular cruise-ship stop in St. Thomas. Shopping sans sales tax is one of the main perks of duty-free finds, and travelers can spend up to $1,600 per family member on items like liquor and linen, as well as jewelry. Just as dazzling? The treasures are displayed in historic buildings crafted from cut coral and Danish bricks transported on trading ships back in the 18th and 19th centuries.
Go Whale-Watching in the Dominican Republic
The Dominican Republic boasts the largest whale-watching industry in the Caribbean, with Samaná serving as a whale-watching hub for harbor tours and trips to the offshore marine mammal sanctuaries of Silver and Navidad Banks. The season takes place between December and March when over 200 humpbacks migrate from Iceland, Greenland, Canada, and North America to reproduce in Samaná Bay. You can spot whales while on land at the Punta Balandra observatory, but for a closer look, hop on board a vessel designed for optimal whale-watching, like Whale Samana’s 55-foot Pura Mia.
Dine in St. Martin
For an island measuring a mere 37 square miles, it’s impressive that St. Maarten/St. Martin has more than 400 restaurants. Some of the best line St. Martin’s small fishing village of Grand Case, considered the Caribbean’s restaurant row. Here, you’ll find everything from laid-back lolos (shack-style, open-air eateries serving traditional creole and barbecue fare) to fancier French bistros, where chefs trained under some of the stars at Michelin-ranked restaurants in Paris.
Discover Alexander Hamilton’s Birthplace on Nevis
The island is one giant history tour, from a museum displaying the western hemisphere’s largest collection of Lord Horatio Nelson memorabilia to the therapeutic hot spring baths that drew poet Samuel Taylor Coleridge. But the island’s biggest claim to fame is a certain “bastard, orphan, son of a whore” we know and love—Alexander Hamilton. You can see the two-story house where Hamilton was born in 1757 (and lived until the age of 9)—a must for theater lovers.
Feel Irie in Jamaica
Reggae was born in Jamaica in the 1960s and is the “heartbeat” of its people. A powerful platform to shed light—and spark change—on social and political situations, reggae rhythms can be heard everywhere from streetside stands and jerk shacks to cafes, nightclubs and at the island’s infamous summer reggae festival. Legend Bob Marley’s hits play on a continuous loop almost anywhere you go and will quickly get you feeling good—or “feeling irie,” as Jamaicans commonly say.
Golf in Barbados
Jamaica, Puerto Rico, and the Dominican Republic feature several stunning golf courses, but Barbados arguably offers better greens, designed by the likes of legends like Tom Fazio and Robert Trent Jones Jr. The island is home to five PGA Standard golf courses in addition to the 9-hole course at Rockley Resort on the southern coast. The courses in Barbados are so iconic, Tiger Woods chose to tie the knot at Sandy Lane, whose greens have also hosted the World Golf Cup Championships.
Soak Up the History of Puerto Rico
The second-oldest city in the “New World,” San Juan’s historic district is a maze of cobblestone streets crowned by two 500-year-old forts. Pose for photos in front of the pastel, Spanish colonial-style buildings before heading to Casa Blanca Museum, Spanish explorer Juan Ponce de León’s former residence, filled with cool artifacts. If you want a glimpse into how Spain created a defense system that controlled access to the Caribbean, Mexico, and South America, tour the forts of El Morro and San Cristóbal along the city wall.
Catch a Sundowner in Antigua and Barbuda
The 490-foot-high Shirley Heights Lookout point hosts a weekly Sunday sundowner party from its perch, which shows off one of the most scenic shots of the bays below. Keep your camera steady as the sun sets behind the ocean, and, if you’re lucky, you’ll be able to snap the money shot of the green jet of light that quickly flits across the horizon. If you miss the sunset, don’t worry; the party carries on late into the evening.
Go Off-Roading in Aruba
Cruise through abandoned gold mines and past twisted divi-divi trees and cacti in Aruba’s desert-like Arikok National Park, which covers 20 percent of the island. See the park on the back of an ATV, hopping off to get a closer look at heritage sites like caves, rock drawings, and rock formations composed of lava or limestone.
INSIDER TIPOpt for a guided tour through dry river beds and to some of the park’s more secluded bays, such as Moro, Boca Prins and Dos Playa, some of the most unspoiled beaches on Aruba.
Swim with Pigs in the Bahamas
A boat tour through The Exuma Cays drops you right on Pig Beach, home of the social media-famous swimming pigs. They’re not native to the island, and the story as to how they landed (or swam) here is still a mystery. Legends say they were intended to be cooked by sailors or survived a shipwreck. Now Big Major Cay is home to about 20 pigs and piglets, and while the only lodging on the island is for—you guessed it—the pigs, the cay is just a quick boat ride away from Staniel Cay (or a lengthier, three-hour trip from Nassau).
Sip Rum Swizzles in Bermuda
This rum-based cocktail—considered Bermuda’s national drink—was first served in Bermuda in 1932 at the Swizzle Inn, the island’s oldest pub. You’ll find a variation on the classic (originally crafted with local Gosling’s Rum), done up with different citrus juices, spices, and Angostura bitters, at nearly every bar and restaurant across Bermuda, where it’s just as iconic as the Sling is to Singapore.
Kayak in Bonaire
Lac Bay’s mangrove forest is one of the best-preserved in the Caribbean. Hop in a glass-bottom kayak and cruise through the lagoon’s natural set of tunnels, pausing for snorkel sessions in some of the more scenic stretches where sea turtles are often sighted. In addition to skirting the north or south shore, you can also kayak over to the smaller, uninhabited island of Klein Bonaire, whose crystal-clear waters and underwater “forest” of black coral is teeming with sea turtles and vibrant fish.
Savor Cuba’s Food
If you’re lucky enough to make it to Cuba, you must try the home-style cuisine at one of the many paladares dotting the island. Independent restaurants were illegal up until the fall of the Soviet Union, but now these privately-owned eateries (typically found inside homes) have sprouted up throughout the main cities of Havana, Cienfuegos, and Camaguey. Dishes are typically scrawled across a chalkboard sign and usually contain ingredients found that same day at markets or surrounding farms.
Cruise to Little Curaçao
Take a two-hour catamaran tour through the deserted coral atoll known as Klein (Little) Curaçao, which sits about 15 miles off Curaçao’s southeastern tip. The main reason to visit the rocky volcanic island? The beach, of course! Klein Curaçao has the longest—and whitest—stretch of sand in Curaçao, making it a top day-trip destination, where the only other inhabitants to greet you are sea turtles. While you’re there, take a walk to the center of the island to see the landmark pink lighthouse.
Take a Dip in Dominica’s Hot Springs
Known as “Nature Island,” Dominica was one of the shooting locations for “Pirates of the Caribbean” thanks to beautiful spots like Morne Trois Pitons, home to five volcanoes and hot springs. Spend the day hiking the Waitukubuli National Trail before soaking in the therapeutic, open-air mud pools and natural hot sulfur springs. Another popular pick: Bubble Beach Spa in Soufriere Bay, a free alternative to some of Wotten Waven’s more touristy sulfur spas.
Go Gallery Hopping Underwater in Grenada
The underwater sculpture park off Moliniere Point is home to more than 60 different statues that are shallow enough to be seen while snorkeling. Set off on a 10-minute ride from what’s arguably Grenada’s most gorgeous beach, Grand Anse, to reach the gallery of concrete-and-steel sculptures. They’re constantly changing as vibrant sponges and algae add color and texture.
INSIDER TIPSince some of the statues are as shallow as 6 feet deep, you don’t need to be a certified diver to fully experience the underwater site; glass-bottom boat tours are great alternatives for those who would rather glance from above.
Enjoy French Fare in Martinique
Cuisine in Martinique plays on the island’s French heritage with a gastronomic version of Caribbean creole. In capital Fort-de-France, you’ll find starred-chef Marcel Ravin’s La Table de Marcel, while lauded local chef Charles Brédas’ namesake eatery sits in the center of the island in agriculturally rich Saint-Joseph. Don’t skip out on the markets. Make your way to one of the many restaurants serving up spectacular local fare right inside Fort-de-France’s Grand Marché, the largest market on the island.
Rock and Roll in Montserrat
Once home to AIR Montserrat, the recording studio founded by Beatles producer Sir George Martin, Montserrat is a worthy pilgrimage for rock fans. The studio played host to famous artists like Sting and Eric Clapton, among the many stars who recorded here in the 1970s and 80s. The studio was destroyed in 1989 by Hurricane Hugo, and while it wasn’t rebuilt, you can still walk through music history at the Montserrat Cultural Centre, admiring the collection of bronze handprints from the recording artists.
Scuba Dive in Saba
Known as “The Unspoiled Queen,” the volcanic island of Saba is teeming with 26 dive sites dotted with coral-encrusted boulders, dubbed “pinnacles,” that rise from the seafloor. Located just a 15-minute flight from St. Martin/St. Maarten, Saba’s natural beauty extends from its green hills to the undersea lava fields, which, when coupled with the 150 different marine species found in the marine park’s waters, make it one of the more visually impressive—not to mention least tourist-filled—dive sites in the Caribbean.
Window Shop in St. Barth
Shopping in St. Barth is like strolling La Croisette in Cannes. Even if you can’t splurge on a new bag at Dolce & Gabbana or timepiece at Rolex, you can still indulge in fantastic window shopping at the island’s 200-plus (duty-free) luxurious boutiques. Start on capital Gustavia’s Rue de la République, where most of the designer brands (Prada, Louis Vuitton) are based. Keep in mind that most shops shut for a long lunch from noon to 3 p.m., as well as on Wednesday afternoons.
Go Treasure Hunting in St. Eustatius
No wonder its nickname is “The Caribbean’s Hidden Treasure”—The sea surrounding the Dutch island of St. Eustatius (called Statia by the locals) is home to sunken ships and its very own spot marked “X”: Blue Bead Hole. At the popular dive site, you can still see 17th-century glass blue beads shining in the sand. They were the local currency of choice for the Dutch West India Company, which traded them for tobacco, cotton, rum, and slaves. Now these beads are the only treasure on the nature-filled island—if you’re lucky enough to find them.
Attend a Friday Fish Fry on Saint Lucia
Join the locals in Anse La Raye near Soufrière during this lively event, when DJs and local musicians amp up the sleepy fishing village. While it’s smaller than the Gros Islet Friday Night Street Party on the north end of Saint Lucia, you’ll find similar food served at the stands and pop-up street cafés lining the beachfront. Dig into freshly caught snapper, lobster, tuna and crab.
INSIDER TIPIf you want to snag the best seats—and selection of seafood—aim to arrive before 7:30 p.m.
Swim with Sea Turtles in St. Vincent and the Grenadines
At the Tobago Cays Marine Park, which is considered the “Jewel in the Crown” of the Southern Grenadines, you can snorkel with green and hawksbill turtles in the protected Baradal Turtle Sanctuary. Later on, head to Petit Tabac, a beach so pristine it was chosen as the backdrop for the deserted island scene in “Pirates of the Caribbean: Curse of the Black Pearl.”
Dance to Calypso in Trinidad and Tobago
The Afro-Caribbean beat began here in the early 1900s, and it’s still going strong in the capital city, Port of Spain. For the full Calypso experience, time your trip around Carnival, when thousands of costumed masqueraders dance through the streets of Trinidad and Tobago in what’s said to be the “biggest street party on Earth.”
Parasail in the Turks and Caicos Islands
One of the best ways to see the most beautiful beach in Turks and Caicos, Providenciales’ Grace Bay, is from above. Keep your eyes peeled while you’re up there: You may spot turtles and dolphins darting through the barrier reef’s coral, starfish in the sandier stretches, and maybe even a famous face or two sunning on the celebrity-owned mega yachts nearby.