Secret Caribbean: Where In-the-Know Island Hoppers Vacation

Congratulations! You survived another February in Chicago—with record-breaking snowfall. If you’re like us, a winter warm-up is exactly what you need right about now. Looking for a Caribbean escape that is slightly off the beaten path? Check out one of these lesser travelled, but oh-so-blissful, Caribbean islands.

Scrub Island

Scrub Island Resort, British Virgin Islands. Photo courtesy of Scrub Island Resort
Scrub Island Resort, British Virgin Islands. Photo courtesy of Scrub Island Resort

They call it Scrub Island. You’ll call it heaven on earth. One resort dominates most of this private island that’s part of the British Virgin Islands—the appropriately named Scrub Island Resort. Scrub Island is the first new resort in the BVIs in 15 years. An on-site sailing school and scuba diving center means there are plenty of activities. Of course, you can just kick back in your hammock or lounge chair at any of the four surrounding white-sand beaches.

Scrub Island’s award-winning double-decker pool, perched on a bluff overlooking the marina, has a slide and two swim-up bars. Not a bad place to spend a few hours. Go exploring in one of the resort kayaks or try your hand at fishing by chartering a boat. Bonus: The resort’s chef will cook up your catch!

The best way to reach Scrub Island is by flying into San Juan, then catching a flight on Seaborne Airlines directly to the Tortola/Beef Island Airport. From there, the resort will pick you up for the five-minute boat ride to the private island, which feels a world away from the hustle and bustle (at least by Caribbean standards) of Tortola. Once there, you’ll find 230 acres of tropical bliss.

 Island Hopping in the British Virgin Islands

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Sailing the British Virgin Islands. Photo courtesy of Voyage Charters BVI

 BVI is all about island hopping. To really experience the region, consider chartering your own sailboat. You’ll be able to reach out-of-the-way coves and beaches that cruise passengers can only dream of.

“The BVIs offer consistent gentle trade winds, warm turquoise waters, and countless protected, sandy anchorages, making it the ideal venue for a sailing vacation,” says Peter Jones of Voyage Charters BVI.

“The close proximity of more than 50 different islands and cays allows you to island hop from one of the world’s largest barrier reefs, to Robert Louis Stevenson’s famed ‘Treasure Island,’ with a string of festive beach bars in between. You get to explore shipwrecks, white sand beaches lined with coconut palms, and vibrant reef teeming with a kaleidoscope of aquatic species.”

Sounds heavenly, right? If you’re new to sailboat chartering, Jones says charter companies make planning a sailboat vacation a breeze, helping with the itinerary and all the details. Voyage Charters will provide your group with a captain or crew or, if you’re an experienced sailor, you can consider going it on your own, bareboat.

Out Islands of the Bahamas

The Bahamas tourism board likes to say “It’s better in the Bahamas.” Audrey St. Clair, managing editor of Islands magazine, agrees. “It’s easy to fly into Nassau, but don’t stay there the whole time,” St. Clair says. “Take a short ferry or inter-island flight to get out—far out—to the Out Islands of the Bahamas.

She recommends unspoiled spots like Harbour Island, where you can swap megaresorts for boutique inns and golf carts take the place of cars. Or, try, Eleuthera, where you’ll likely have the powder-white beach to yourself. And in the Exumas, St. Clair says diving into a 400-foot-deep blue hole is just another day on the water.


St. Clair also steers winter-weary Midwesterners to this island in the Lesser Antilles: “Anguilla consistently tops ‘Best Beaches’ lists, and the brand-new beachfront Zemi Beach Resort & Spa sits on one of its most acclaimed strands, Shoal Bay East.”

You’ll never want to leave Anguilla’s Zemi Resort, and (for a price) you don’t have to. “Several of the residences are available for purchase,” St. Clair says.

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Anguilla’s Zemi Beach Resort & Spa. Photo courtesy of Zemi Beach Resort & Spa


A former Dutch colony, Curacao (pronounced keer-ah-sow) is a self-governing island off the coast of Venezuela that remains part of the kingdom of the Netherlands. The pastel buildings look so picture-perfect, you’ll think you’re on the movie set for a quaint Caribbean island. It’s clean, colorful and everyone seems friendly.

Like much of the Caribbean, it’s a wild mix of cultures. Over the years, it’s been ruled by the Spanish, French, British and Dutch. Today, the average islander speaks an incredible four languages—Dutch, English, Spanish and Papiamentu, their own Creole mix.

Curacao’s Big Knip Beach. Photo courtesy of Andrea Guthmann

Divide your time between the capital city, Willemstad, and the idyllic beaches one hour away on Curacao’s west end. Dutch investor and philanthropist, Jacob Gelt Dekker, has made it easy to do that with his two hotels, each named Kura Hulanda. Willemstad’s Kura Hulanda Village is made up of historic homes restored to original splendor, connected via cobblestone paths. The hotel complex is part of a UNESCO World Heritage Site, sitting on what was once the Caribbean’s largest slave market. An incredible on-site museum explains the history of the site and houses Dekker’s own collection of African art and artifacts.

Curacao has plenty of sights to see beyond the beaches, including the Western Hemisphere’s oldest Jewish synagogue. Book a guided tour of Willemstad through the Curacao Tourism Board to get a full understanding of the island’s rich history.

Willemstad, Curacao. Photo courtesy of Andrea Guthmann.

When it’s time to eat like a local, order up a lunch of goat stew and plantains at the Old Market, behind the Willemstad Post Office, next to the outdoor fish and produce market. Need a perfect spot for a romantic sunset dinner or drink? Head to Saint Tropez, an oceanfront restaurant in the uber-hip, yet incredibly welcoming, Pietermaai entertainment district, a pleasant 10-15-minute walk from Kura Hulanda Village.

A complimentary one-hour shuttle takes guests from Willemstad’s Kura Hulanda Village past the island’s arid landscape to the postcard-perfect beaches on Curacao’s west end. Once you arrive at the Kura Hulanda Lodge & Beach Club, you’ll find your desert oasis—a turquoise blue ocean, luxurious pool surrounded by palm frond huts, and an on-site dive center. Daily two-and-a-half-hour snorkel trips with Go West Diving cost $30 for the first person and are half-price for the second when you bring your own equipment.