Final Frontier | U.S. Virgin Islands

Honeymoon spot? Think again. America’s Caribbean is the stuff of family fairy tales.

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  • Photo: Joanna Batt

    Annaberg Sugar Plantation in St. John

  • Photo: Chris Smith

    Children play on the beach at Bolongo Bay Beach Resort on St. Thomas.

  • Photo: Courtesy of The Buccaneer

    Guests frolic in the Caribbean waters off the shore near The Buccaneer resort in St. Croix.

  • Photo: Courtesy of The Buccaneer

    Guests frolic in the Caribbean waters off the shore near The Buccaneer resort in St. Croix.

  • Photo: Don Hebert

    Hassel Island

  • Photo: Courtesy of Wyndham Sugar Bay Resort

    Hassel Island

Photo: Joanna Batt

Annaberg Sugar Plantation in St. John

When I was a kid, my folks weren’t the type to skedaddle off on a parents-only getaway. For better or for worse, we’d create a family scene in some exotic destination.Too bad we never discovered the U.S. Virgin Islands, a place where you’re just as likely to sip rum punches on a beach as you are to take a synchronized-swimming lesson with your kids—plus a pod of friendly sea lions.


I admit: I had sized up America’s Caribbean as high on romance, not so big on kid-friendly culture. But after visiting all three no-passport-required islands (just east of Puerto Rico—about 1,100 miles from Miami, as the crow flies), I was delighted to discover I couldn’t have been more wrong.


Following six hours of travel from Chicago (a Florida layover breaks up the trek), start your journey in St. Croix. Home to rum distilleries and troves of pirate lore, St. Croix is where you’ll get some seriously unaltered island flavor. After checking in to the Buccaneer (800-255-3881, thebuccaneer.com), with a kids’ club that boasts crab races, or Divi Carina Bay (877-773-9700, divicarina.com) for slightly cheaper lodging that hardly skimps on ocean views, take in the island via Tan Tan Jeep Tours (340-473-6446, stxtantantours.com). Kids will freak for the adventure-style ride, which includes stops at local smoothie shacks, off-roading in the rain forest and tide-pool swimming.


But no jet-setting until you’ve basked in the snorkeling paradise of Buck Island: A half-day excursion via Big Beard’s Adventure Tours (bigbeards.com; $70, kids $22–$55) gives kids plenty of time for a snorkeling intro and underwater “hike” along the National Monument’s coral reef. Don’t leave the island until you’ve devoured fried chicken and johnnycakes at La Reine Chicken Shack (340-778-5717).


Next up is St. Thomas, with cozy lodging at the family-run Bolongo Bay Beach Resort (340-775-1800, bolongobay.com). Get busy with shark petting, turtle encounters and hands-on swimming with rescued sea lions at Coral World (340-775-1555, coralworldvi.com; $19, kids $10, family pass $60). While the blood’s still pumping, check out VI Ecotours (847-845-2925, viecotours.com) for a guided kayak tour of the bay’s Hassel Island, home to ruins of British naval forts, with both snorkeling and hiking pit stops.


Last but not least, St. John beckons with the most drop-dead-gorgeous beaches. Although there’s not a bad one to be had, soak in Caneel, Cinnamon and Trunk Bays, which provide picture-perfect backdrops for snorkeling and swimming. The Westin (340-693-8000, westin.com/stjohn) has a kids’ club with beachside movies and meals, but attractions beckon—like the creepy ruins of the long-abandoned but still intact Annaberg Sugar Plantation (vinow.com) tucked amid the blooming frangipani, or shopping for watercolors, pint-sized paddleboards and more at Mongoose Junction (mongoosejunctionstjohn.com).


Don’t be surprised when so many of the islands’ friendly locals aren’t exactly local at all: Turns out, they originally hail from cities on the mainland (including, yes, Chicago). They visited, fell in love with the islands and simply never left. Who knows? Perhaps you and your family will be so lucky.



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