How To Choose The Right Caribbean Island For Your Vacation

Best for Romance: St. Lucia

Located in the Windward Islands just south of Martinique, St. Lucia is a tropical paradise for lovebirds of all kinds. The breathtaking vistas in this lush, mountainous island are enough to make even the most jaded of hearts believe in love again. Two volcanic spires of the Twin Pitons offer an absurdly romantic view as they jut against a turquoise horizon, a blend of Caribbean Sea and sky. At sunset, this view is even more tremendous—made ideal by the fact that the most romantic resorts in St. Lucia take advantage of their natural surroundings. Ladera Resort and Jade Mountain feature seaside suites exposed to the blissful surroundings, with only three walls to protect guests from the elements. If you'd rather opt for more privacy, consider a chic seaside cottage at Sugar Beach, a Viceroy Resort with a luxurious yet laid back ambiance that's perfect for falling in love.

Best For Surfing: Barbados

As the easternmost nation within the Caribbean island chain, Barbados is surrounded on every side by the Atlantic—which is why the waves are so spectacular in this part of the world. Beginners looking to catch their first wave should head to Batts Rock Beach. Even if you don't have any success, the setting is gorgeous and the snorkeling is spectacular, so the day won't feel like a loss at all. Hit up La Cabane afterward to enjoy the beach-chic ambiance and delectable cocktails. Once you’ve mastered the skill of hanging ten, head to the legendary (and aptly-named) Surfer’s Point in the capital of Bridgetown, or Bathsheba Beach in Saint Joseph Parish. Bathsheba Beach is home to the Soup Bowl, an iconic break that is a favorite of none other than surf icon Kelly Slater. With any luck, the two of you will be catching waves together sometime soon.

Best for Luxury: Antigua

While many people consider St. Barth's to be the epitome of Caribbean luxury, we believe true luxury is being able to get away from it all while still enjoying world-class comfort and amenities. This brings us to Antigua, which is part of the Twin Islands of Antigua and Barbuda. The natural beauty of the destination is breathtaking, with some of the most gorgeous hillside vistas in all the tropics.

While Half Moon Bay is celebrated as being one of the most beautiful beaches in the world, the shoreline isn't quite long enough to satisfy multiple chaise lounges—much less accommodate your very own seaside villa overlooking the water. For the latter, head to Carlisle Bay Resort in the town of Old Road in Saint Mary Parish, Antigua. At this beautiful, secluded property, you can enjoy elegant meals on the beach and a backdrop of lush, tropical rainforest. And if a private beach isn't enough, head to Jumby Bay to get a taste of your own private island; 300 acres of Caribbean paradise await the traveler, only two nautical miles off the coast (less than 10 minutes via private yacht). Trust us, you're worth it.

Best for Beaches: Turks and Caicos

When it comes to beaches, the Turks and Caicos Islands are simply without rival. Thanks to the archipelago's limestone foundation and the shell and coral origin of its blindingly bright sand, the coastline juxtaposes vividly against the glistening aquamarine waters. And, though the beaches are spectacular throughout the islands, if you want to truly appreciate tropical bliss, head to South Caicos, one of the more undiscovered islands within Turks and Caicos. Book a room at Sailrock Resort, where you can spend your days enjoying the heavenly atmosphere in perfect solitude, undisturbed.

Best for Culture: Jamaica

Though the distinct heritage of each Caribbean island is worthy of exploring, we’re partial to Jamaica because of our loyalty to three things: jerk chicken, Bob Marley, and Jimmy Cliff. And there's no shortage of cultural activities and outings to embark on all over the island nation. Check out the Montego Bay Cultural Center and, when in Kingston, visit the Bob Marley Museum as well as the heritage site of Devon House (pictured above). Visit Accompong Village via Accompong tours, which takes you to the more rural region of the island, Cockpit Country. When in Cockpit, drink rum at Appleton Estate and visit Good Hope, a sugar estate first established in 1774. If you want to visit the smaller villages, look into a culturally-immersive program like the Country-Style Community Tour, which helps teach visitors about the culture and heritage of Jamaica. 

Best for Families: The Bahamas

For families, it's hard to beat the Bahamas for a family-friendly Caribbean vacation—the capital of Nassau, on the island of New Providence, to be specific. There's just an unbeatable array of options to suit everyone: culture, nature, and world-class island cuisine (check out Tru Bahamian Food Tours if you don't believe us).

And you don't need to day-trip to the far outer islands for adventure. Book a 25-minute boat ride and adventure with Harbour Safaris or Sandy Toes to get to Rose Island, located merely three miles off-shore. While you're there, check out the spectacular snorkeling over the coral reef line, home to two shipwrecks and tropical fish.

Best for Nightlife: Puerto Rico

San Juan, Puerto Rico, is the virtual capital of the Caribbean, the region's only true "city," and home to the most diverse nightlife, from all-night, Latin-flavored dance halls to fine restaurants, casinos, bars, and cockfights. San Juan also has the region's best gay nightlife, and Puerto Rico has long been a gambler's mecca; the Wyndham El San Juan is perhaps the best-known casino, while the new Wyndham Rio Mar is one of the nicest. Truly anything and everything is possible after the sun goes down here.