Guide to 6 Enticing Vacation Getaways

Explore your island’s nooks and crannies via easy boat rentals

Going on a Caribbean island vacation allows you to pause your regular routine, and invites you to relax and rejuvenate your body and spirit. Whether you choose an island that’s chock-full of outdoor activities, or prefer a slower-paced locale where you can snooze on a gorgeous beach, you’ll likely come home with an entirely new perspective and a sun-kissed glow.

Northern Caribbean

A northern Caribbean trip often minimizes your travel time while promising a memorable island experience. Depending on your departure point, you might arrive just in time for a sundowner at your hotel’s tiki bar. And if not, relax – there’s always tomorrow.

Cayman Islands

The Caymans are a preferred vacation spot, largely because the three-island group offers convenient travel options for North American visitors.

Grand Cayman: The nation’s largest and most commercially developed island is a regular cruise ship destination, and is also home to several all-inclusive resorts.

Cayman Brac and Little Cayman: If you’d prefer a slower pace with fewer crowds, these smaller islands make a good choice. If you’re a SCUBA diver, these islands offer superb barrier reefs with tons of colorful fish. In fact, you’re likely to experience some of the best diving in the entire Caribbean.

Turks & Caicos

Adjacent to the southern Bahamas, the Turks & Caicos prides itself on being an off-the-beaten-path getaway. The island nation is comprised of 40 islands and cays, many completely uninhabited.

Looking everywhere, you’ll see brilliant white sand and blue-green water that defies description. Just offshore, thriving coral reefs beckon divers. In fact, little Salt Cay has one of the most expansive offshore reef systems in the world.

Providenciales (also called “Provo”): This cruise ship port boasts numerous luxury hotels, restaurants, and a higher level of commercial development. However, it’s still an appealing destination.

Grand Turk: This low-key town nicely showcases the islands’ history and culture. In fact, Christopher Columbus chose Cockburn Town as his first stop in the Western Hemisphere.

British Virgin Islands

The British Virgin Islands, or BVIs, are a longtime Caribbean vacation favorite, partly because you won’t find large-scale commercial development here. In fact, the islands’ resorts, lodgings, restaurants, and attractions have remained low key and secluded while catering to well-heeled travelers.

Sailors also love the BVIs, as the nation’s 60 islands and cays offer countless scenic anchoring spots while inviting you to island hop with ease. In fact, the BVIs are a great place for boat rentals, especially with a knowledgeable captain.

Tortola: Here, you’ll find impressive cliffs and beautiful white beaches. Resorts and hotels dot the island, each one offering a slightly different lodging experience.

Jost Van Dyke: Just a short sail from Tortola, this laid-back island tempts visitors with tasty Caribbean food and legendary libations, plus fishing and diving excursions.

Virgin Gorda: After visiting The Baths, you’ll marvel at this often-photographed beach containing huge granite boulders and secluded grottoes washed by the waves.

Anegada: This sleepy, secluded little island entices BVI travelers with beautiful beaches. To find it, keep a sharp eye, as the island is so flat that it almost blends into the Caribbean Sea.

U.S. Virgin Islands

Frequently called “America’s Caribbean Paradise,” the USVIs are an appealing destination that doesn’t require United States citizens to obtain a passport. The three islands each have a different character, and exploring them is like enjoying a tasty meal with three satisfying courses.  

St. Thomas: Charlotte Amalie, the USVI’s capital, contains a mix of hilly settlements and turquoise harbors. This city is on the cruise ship circuit, and you’ll likely see mega-yachts bobbing at their moorings. After upscale vacationers arrive on the island, they’ll find plenty of lodging, shopping, and dining options.

St. John: Just a short ferry ride from St. Thomas, beautiful St. John appeals to a different clientele: vacationers who prefer natural beauty and seclusion. The island’s 7,000+ acres of parkland blend into unspoiled beaches, and most hotels and resorts have a low-key vibe.

St. Croix: After an ambitious trip south, you’ll reach less-visited St. Croix, sprinkled with sugar cane plantations and rum distilleries. Take a guided horseback or eco-tour, or engage in a vigorous game of tennis or golf. Or, treat yourself to a relaxing day at the spa.

If you’re a SCUBA diver, explore St. Croix’s beautiful reefs, populated with numerous corals and fish. And speaking of fish, the Virgin Islands have racked up some serious fishing records. Try your hand at angling by booking several convenient boat rentals.

Southern Caribbean

Taking a southern Caribbean vacation is like finding a pearl in a bucket of oysters. You’ll expend some effort to reach your goal, but the reward is definitely worth it. Once you get to your island destination, relax and enjoy yourself even during hurricane season, as the odds of problem weather are very low. So, kick back and put yourself on island time!

St. Lucia: This lushly forested island appeals to diverse vacationers. Some visitors are honeymooners who prefer seclusion, while others are music fans who come for the St. Lucia Jazz & Arts Festival. At the other end of the spectrum, you’ll find thrill seekers who spend their time climbing the Pitons or zip-lining through the rain forest. Whatever your pleasure – you might just find it in St. Lucia.

Curacao: If you enjoy your Caribbean scenery mixed with history, you’ll enjoy Willemstad, Curacao’s main port city. This good-sized settlement contains brightly colored Dutch colonial buildings that give it an Old-World European look and feel. Outside of Willemstad, Curacao has a desert-like landscape, reflecting its unusual semi-arid climate.

And then you get to the beaches, which feature scenic bays and coves lapping at gorgeous white sand. Snorkelers and divers will enjoy the many well-populated reefs, providing another excuse to visit this off-the-beaten-path island.

Book those island boat rentals, and discover out-of-the-way scenic spots you won’t forget

If off-the-beaten-path island exploring sounds like fun, make your dream happen by contacting Boatsetter, the leading boat-sharing company that makes it super-easy for boaters and local boat owners to get together. Even better, you can hire an experienced captain to handle your boat rentals while you relax and enjoy the scenery. Here are several of the nicely equipped boats in the Boatsetter fleet.

Beneteau Beneteau 44

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Victoria Lazzara 68'

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Fountaine Pajot Orana 44

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