Island Lovers Guide to the Caribbean

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With such a diverse array of activities and atmosphere, committing to a destination in the Caribbean can seem daunting. Remote and secluded or energetic and thriving? Relaxation or adventure and intrigue? With an insider tip or two, all this variety needn’t be so mystifying. Here are a few simple guideposts to help you find the island that’s calling your name…

Jamaica
The eclectic island
There is so much more to Jamaica than rum and revelry! Like the Cockpit Country, the almost totally untouched inland that is a Mecca for wildlife tours and even spelunking. Or tiny Nine Mile, where you can draw inspiration from Mt. Zion Rock where Bob Marley used to practice his guitar. If you have an appreciation for architecture, consider a visit to Rose Hall, a magnificent i8th-century three-story plantation manor set on 4,000 acres overlooking the sea. No matter who you are, Jamaica has something for everyone. Venture beyond the popular resorts and there’s no telling what you’ll find!
The Bahamas
A suburb of Atlantis
Mystery lovers, this is the place for you! Off the coast of North Bimini Island is one mind-boggling scuba dive. Submerged beneath the sea is the Bimini Road, a collection of giant, as yet unexplained, stone blocks set into what appears to be a highway. Some say it is a remnant of a long-submerged highway to Atlantis—or even a wall of the city itself. When you’re done trying to wrap your mind around the Bimini Road, there are mangrove forests, coral reefs, idyllic beaches and over 700 other islands to explore, including Crooked Island, the site of Columbus’ second New World landing.
Turks & Caicos
A vacation less ordinary
The Turks & Caicos islands can be summed up in one word: variety. There is South Caicos, with its compact, rough-around-the-edges bohemian village of Cockburn Harbor, where wild horses and donkeys roam the streets. Or there is Grand Turk, home to the stately 400-year-old capital of Cockburn Town. Tiny Salt Cay is remote and hardly developed, with only two hotels taking residence on its beaches. Add in the world’s third-largest reef system, which consistently ranks as one of the world’s top ten scuba diving locations and you have a very unique archipelago.
U.S. Virgin Islands
St. Thomas & St. John
Paradise without a passport
St. Thomas is quintessential paradise, with heavenly beaches, fantastic watersports and a delightful colonial village atmosphere, where quaint streets are lined with shops specializing in perfumes and glittering diamonds. All this is set into a spine of densely forested hills and ridges that divide the island into a series of tranquil, turquoise bays and coves. By contrast, tiny St. John is much slower-paced and almost entirely pristine, with two-thirds of the island under the Park Service’s protection. This is an island where you can have a tranquil beach entirely to yourself before heading up a hiking trail to the top of an emerald green plateau looking out over the sea. Look closely and you may spot a petroglyph or two.
Dominican Republic—Punta Cana
The best of both worlds
Why force yourself to choose between city life and the relaxation of the beach when you can have the best of both? The Dominican Republic provides both idyllic white-sand beaches and bustling city life in Santo Domingo. And everything the Dominican Republic does, it does the best, from Cabarete Beach, regarded by enthusiasts as the world’s best place to windsurf and kiteboard, to wonderful Punta Cana. Relaxed, quiet, and tranquil, Punta Cana is imbued with European sophistication. And with golf, tennis, horseback riding, scuba diving and sport fishing all readily accessible, rest assured there’s plenty more to do than just sip cocktails in a beach chair.
Trinidad & Tobago
The odd couple
Trinidad and Tobago couldn’t be more distinct—which is precisely what makes them such a perfect getaway. Trinidad is thriving and cosmopolitan, home to the capital city, Port-of-Spain, and its collection of gorgeous i9th-century Colonial buildings that line its beaches. In contrast, tiny Tobago is relaxed, slow-paced, and relatively undeveloped. Argyle Falls, a triple-tier waterfall, is not-to-be-missed. The hike up to it, punctuated by natural pools perfect for cooling off on the way, is well worth the trek.
Martinique
Paris comes to paradise
A trip to Martinique is like visiting Paris’ Caribbean cousin.
The locals wear French fashions and eat croissants, and its capital, Saint-Pierre, with its wrought-iron balconies and windows framed by shutters, feels like turn-of-the-last-century Montmartre. There’s even a museum, Le Carbet, dedicated to one of France’s most famous painters, Gauguin, who once called this island home. All of this backs up to Martinique’s real draw: Les Salines, a wide, undeveloped beach that is so immense you will feel as though you have it all to yourself. It’s pure remote paradise, with a
French accent.
Cayman Islands
The jet-setter’s getaway
The playground of the James Bonds of the world, the Caymans are slick and worldly, filled with fancy boutiques, posh condos and resorts with all the modern conveniences. There’s even a burgeoning arts scene, centering around the National Gallery of the Caymans. But for a break from all the jet-setting, venture inland to Hell, a town filled with bizarre black rock formations which the town’s founder thought resembled piles of brimstone; or retire to one of the smaller, nearly unpopulated islands like Cayman Brac or Little Cayman for a little peace and quiet before re-joining the flashy revelry.
Can’t decide which island is for you? Caribbean cruises are a great way to get a taste of several islands packed into one vacation.

A Caribbean island lover’s guide is the perfect companion to any cruise itinerary. For more Caribbean inspiration, our advisors’ 5 Caribbean Experiences That Will Change Your Life guide captures the most transformative Caribbean encounters.

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Sue Lobo
Sue Lobo is a four-time Condé Nast Traveler Top Travel Specialist (2023, 2024, 2025 & 2026) and Senior Travel Advisor at Atlas Travel Center, one of the most decorated travel agencies in the United States. With more than 35 years of experience in the travel industry, Sue has planned, booked, and personally accompanied trips for thousands of clients — from first-time cruisers to seasoned luxury travelers who have circled the globe multiple times. Sue's areas of deep expertise include ocean and river cruising, European tours, group travel coordination, luxury travel, honeymoon planning, and family vacation design. She is a CLIA-certified cruise specialist and works within an agency that holds IATA and ARC accreditation and maintains an A+ rating from the Better Business Bureau. Over her career, Sue has been involved in more than 30,000 bookings and has personally coordinated over 200 travel groups — from faith-based group cruises and HBCU alumni trips to women's retreats, family reunions, and corporate incentive travel. What sets Sue apart is not just the credentials — it is the firsthand experience behind them. Sue has personally traveled to more than 20 countries across three continents, including Cuba, Egypt, the United Arab Emirates, and throughout Europe. She has sailed on dozens of cruise ships across nearly every major line, walked the river cruise routes she recommends, and eaten at the restaurants she suggests to clients. Her recommendations come from personal experience, not brochures. In addition to advising clients, Sue writes extensively about travel for The Traveler's Atlas blog — covering everything from cruise line comparisons and overtourism trends to destination guides and practical travel tips. Her writing is grounded in the same expertise she brings to every client conversation: honest, specific, and built on decades of real-world travel experience. Sue is based in the United States and available to help travelers plan cruises, European tours, group trips, river cruises, honeymoons, family vacations, and more. To work with Sue, contact Atlas Travel Center at atlastravelweb.com.