- 1 Best for Sport: Barbados
- 2 Best for Sport: Grenada
- 3 Best for Sport: Virgin Gorda
- 4 Best for Honeymoons: Anguilla
- 5 Best for Honeymoons: St. John
- 6 Best for Honeymoons: St. Lucia
- 7 Best for Friends: Puerto Rico
- 8 Best for Friends: St. Thomas
- 9 Best for Friends: Turks & Caicos
- 10 Best for Families: Bahamas
- 11 Best for Families: Bermuda
- 12 Best for Families: Dominican Republic
- 13 Best for Food: Jamaica
- 14 Best for Food: Martinique
- 15 Best for Food: St. Barts
A Caribbean Island for Everyone
Suffering from Caribbean island indecision? Whatever you want from your tropical fix, Leigh Crandall has a stretch of sand to suit you
Best for Sport: Barbados
The mighty Soup Bowl surf break slams the east coast of Barbados and draws pros from all over the world (Kelly Slater included). This side of the island has peace and quiet as well as great surf to recommend it, with a locals-only vibe and a ragged, sandy shore scattered with boulders and casual seafood joints instead of fancy five-star hotels. Hit up seventh-gen-Barbadian Alan Burke for a surf lesson, and don’t miss the Sunday brunch at the Atlantis Hotel.
Best for Sport: Grenada
With more than 50 top-notch dive sites, this small southeast Caribbean island should be on every scuba enthusiast’s bucket list. Among the best is Molinere Bay, home to a striking underwater sculpture garden by artist Jason de Caries Taylor. Nearby is Flamingo Bay, part of the island’s Marine Protected Area where underwater explorers will spot elkhorn coral, yellowtail snapper, banded jaw fish and seahorses. Grenada also has 20 wreck-dive sites including the “Titanic of the Caribbean,” the cruise liner Bianca C, where divers are likely to spy larger marine creatures, like eagle rays, nurse sharks and barracuda.
Best for Sport: Virgin Gorda
This British Virgin Island’s main attraction is the Baths, a series of giant granite boulders positioned along the beach to create a maze of tunnels, tidal pools and grottos visitors can hike and explore. Some of the best snorkeling in the Caribbean can be found just off the shore here (arrive before 10 a.m. to avoid the hoi polloi). Above the surface, trade winds provide excellent sailing conditions year-round. Visit the Bitter End Yacht Club, which runs a sailing school with classes ranging from Keelboat Basics 101 to bare-boating a 30-footer. You can also learn to windsurf and kitesurf here, then toast your efforts with a Pain Killer — a local rum drink made with pineapple and orange juices, cream of coconut and fresh nutmeg — at the Clubhouse Grille.
Best for Honeymoons: Anguilla
Tucked away in the northern part of the Lesser Antilles, this low-key British island is a great choice for couples looking for quintessential Caribbean scenery (white sand beaches and turquoise seas) without an overly touristy scene. With more than 30 beaches, there’s a sandy spot for every occasion: Savannah Bay for Crusoe-like isolation, Upper Shoal Bay for snorkeling and Rendezvous Bay for live music. Disobey the no-swimming-after-eating rule at Shoal Bay East, where the creamy sand is dotted with beach bars like Uncle Ernie’s — fresh-caught fish and a rum punch is the must-order.
Best for Honeymoons: St. John
It’s still possible to feel utterly alone on the smallest of the U.S. Virgin Islands: 60 percent of the island is protected as a national park, and the beaches are gloriously empty. Hike the milelong Lind Point Trail from downtown Cruz Bay to the secluded, windswept Salomon and Honeymoon Beaches in the morning or, for a dip around dusk, drive to Hawksnest Beach for excellent body surfing at high tide. For a casual meal, catch sunset at the ocean-facing bar at Jax Lounge at the Gallows Point Resort or, if it’s a special occasion, arrange a candlelit meal on the beach at the boutique Caneel Bay Resort.
Best for Honeymoons: St. Lucia
St. Lucia’s majestic Pitons set the tone for a romantic island getaway — add a villa with a private pool at such resorts as Jade Villa, Ladera and Cap Maison, and a couples massage at spas like Kai Belté at Anse Chastanet, and you’ve got honeymoon perfection. If you can persuade yourselves to leave the resort, hike the 2,600-foot Gros Piton together for OMG views. The underwater sights are just as awe-inspiring, with world class dive sites like Coral Gardens and Superman’s Flight, home to schools of angel fish, giant barrel sponges and more.
Best for Friends: Puerto Rico
There’s an activity to suit everyone in your crew within striking distance of Puerto Rico’s capital city, San Juan. Outdoorsy types can explore the tropical canopies and waterfalls of the El Yunque rain forest by day, then kayak the glowing bio bay in Fajardo by night. City slickers can browse the art galleries and shops of Old San Juan and spend the evening salsa dancing at such local spots as the Nuyorican Café. One thing everyone can agree on is the city’s evolving culinary scene. We like El Picoteo, a lively tapas restaurant in an open-air courtyard at the historical El Convento Hotel, where the specialties include empanadillas (turnovers with Spanish sausage, cheese, meat or lobster).
Best for Friends: St. Thomas
Kick off your trip with a visit to Hull Bay, one of the few St. Thomas beaches without a hotel, and less crowded than popular Magens Bay. Rent standup paddleboards from Bluewater outfitters, then reward your efforts with a rum punch and grouper taco at mellow beach bar the Hull Bay Hideaway. After the sun sets, visit Iggie’s Beach Bar in Bolongo Bay for live reggae and calypso, and dancing until the wee hours. Shoppers should save an afternoon for wandering the stores along the cobbled alleyways of downtown Charlotte Amalie. Our favorite souvenir: a pair of bespoke leather sandals from Zora of St. Thomas, who has been making shoes by hand since 1962.
Best for Friends: Turks & Caicos
Very special hotels at a variety of price points, plus a plethora of villa rental options mean the Turks and Caicos Islands work well for groups on a variety of budgets. Hit the beach or opt for more active endeavors like bonefishing, golfing, diving and sailing — there’s even a pair of casinos for the high rollers in your group. For a truly awe-inspiring experience, visit between January and March, when humpback whales migrate through the seas here, and hop a whale-watching tour with operators like Salt Cay Divers.
Best for Families: Bahamas
If there’s one thing the Bahamas offer it’s diversity, with family-friendly hotel options running the gamut from eco-chic boutiques to the behemoth that is Atlantis on Paradise Island. There are endless activity options to keep the clan happy across the archipelago, from hiking Lucayan National Park on Grand Bahama to top tier bonefishing on Andros. For a fun and educational experience for the kids, visit the interactive Pirates of Nassau Museum, which includes a replica of the pirate ship Revenge.
Best for Families: Bermuda
The pink sand and calm, clear water appeal to all ages on the island of Bermuda. When you’re ready for a break from the sun, head to Crystal Caves, where amateur spelunkers can explore the stalactites and stalagmites of one of the largest caverns on the island. Drop by the Bermuda Underwater Exploration Institute for exhibits on the Bermuda Triangle, a submarine simulation and a virtual shark cage.
Best for Families: Dominican Republic
The DR’s affordable all-inclusive hotels aren’t its only family-friendly assets: Santo Domingo offers myriad group outing options, including the National Aquarium and the Trampolin Children’s Museum. Mantai Park in Punta Cana is worth a visit too, with 81 square miles of tropical rain forest and family-friendly shows starring horses and parrots, plus the chance to swim with dolphins.
Best for Food: Jamaica
Spice up your vacay with the Caribbean’s most idiosyncratic cuisine, which blends African, Indian, French and British flavors. You’ll find jerk chicken, pork and fish everywhere from smoky roadside stands (Sweetwood Jerk Joint in Kingston is one of our favorites), sit-down stalwarts like Norma’s Beach Restaurant and upscale hotels, including 007 birthplace Golden Eye, which does an excellent ackee and saltfish, too.
Best for Food: Martinique
This island’s food scene is on the up and offers a sophisticated blend of African and French flavors. Survey the raw ingredients at the covered market in Fort-de-France, then go dine at Capest Lagoon Resort & Spa, where chef Guillaume Bregeat serves such dishes as poached mahi-mahi with coconut milk at Belém overlooking the water. For a more casual bite, hit up Guy Ferdinand’s French/Creole beachside food stand Le Petibonum in Le Carbet. Don’t leave without slurping the local Ti’ Punch, made with white rhum agricole, lime and sugarcane syrup.
Best for Food: St. Barts
St. Barts’ cuisine is almost as high-profile as its jet-setting crowd. In Gustavia, chef Laurent Cantineaux (formerly of Daniel in New York) serves highfalutin fare like foie gras with scallops in an elegant setting with 180-degree views of the harbor. Maya’s is run by a husband-and-wife team and has an ever-changing menu that’s strong on fresh fish, like wahoo and red snapper. For people watching as first-class as the chow, check out open-air Do Brazil; for local color, visit the family-run Au Regal in Corossol, where fishermen gather in the afternoon to swap tales and watch soccer over fresh cod fritters.