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.
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Sue Lobo
Sue, our esteemed Operations Manager, has been honored as a Top Travel Specialist by Condé Nast Traveler for 2023 and 2024. With over 25 years of experience in the travel industry, Sue brings a wealth of expertise to our company, particularly in the areas of group travel, event planning, and blogging. As a passionate traveler herself, Sue has explored more than 20 countries across three continents, including captivating destinations such as Cuba, Egypt, and the United Arab Emirates. Her firsthand experiences allow her to provide invaluable insights and recommendations to our clients, ensuring that their travel dreams become a reality. Sue's dedication to the travel industry extends beyond her role as Operations Manager. She has successfully coordinated over 200 travel groups, meticulously planning and executing each trip to perfection. Her attention to detail and commitment to excellence have earned her a reputation as a trusted and reliable travel professional. In addition to her operational expertise, Sue is a gifted writer at heart. She leverages her writing skills to share her love of travel and provide consumers with essential industry-related news and updates. Her engaging blog posts offer a unique perspective on the world of travel, inspiring others to embark on their own adventures. When she's not planning extraordinary trips or writing captivating travel content, Sue indulges in her passion for cooking, exploring the diverse flavors and culinary traditions of the places she visits. With her unwavering enthusiasm and extensive knowledge, Sue continues to be an integral part of our team, ensuring that every traveler's experience is truly unforgettable.