Trade Winds & Second Chances: Rediscovering the British Virgin Islands by Boat

Virgin Gorda: The Baths Without the Crowds

Virgin Gorda’s Baths were next, a bucket-list stop and proof that the BVI have been fully “discovered.” We avoided the throngs of families by swimming the outer route around the famous grottoes and rock caves, trading hiking trails for deep blue water and a solid workout.

Bitter End Yacht Club and Saba Rock followed; both are beautifully rebuilt. We explored the new Billionaire Bar, a tribute to Sir Richard Branson’s adjacent Necker Island, an aquarium memorial to legendary diver Bert Kilbride, and even took a dinghy ride to tour nearby Biras Creek Resort, still deep in reconstruction. Gifted fresh herbs and veggies from the farm-to-table garden enhanced dinner that night.

We lost one full day, spent leisurely on the hook, to maintenance when our charter’s batteries died, underscoring an important lesson: Make sure your charter company has solid emergency support on standby.

Jost Van Dyke: Foxy’s and the Soggy Dollar

We finally unfurled the sails en route to Jost Van Dyke, trading engines for wind. Dave, raised reluctantly in a sailing family, instinctively jumped in to help with lines. I observed the spectacle and the sound of the wind beating the sails. Sailing is powerful, elegant—and a lot of work. We remain pro-motor.

Jost Van Dyke hosts the legendary Foxy’s, Soggy Dollar and Bubbly Pool. Foxy’s still delivers funky charm, run now by the founder’s daughter Justine as his wife Tessa brightly sashays throughout the properties. While other local spots feel weathered or dormant, Foxy’s Taboo, named for Foxy’s dog, offered a new, quieter beach bar, a good hike to the natural bubbling pool. Then we hailed a spirited cabby, riding up and down the winding hills to the Soggy Dollar for Painkillers, conch fritters, and a beach buzzing with charter energy.

We dove with the Jost Van Dyke Dive Shop’s legendary Colin Aldridge, not only a dive expert but also an ecologist who spent years working with cruise ship and yacht captains and the BVI government to preserve the area’s rapidly diminishing coral reefs. He remains enthusiastic about the volcanic formations and fish-filled caves, and while we snorkeled above them, he and Captain Greg explored The Cathedral cave—a highlight of the dive.

Norman Island: Snorkeling and Pirate Legends

Cane Garden Bay was a visual and audible assault, swarmed by cruise ship crowds. The colorful beach then became blissfully calm and empty once the Disney ship patrons departed promptly at 2 p.m. We then returned to Norman Island to visit the infamous Willy T’s ship bar where partiers throw back shots then jump off the upper deck into the clear blue water.

As always, powerboating made the world small. Conversations turned to performance, older Midnight Express, former drug interdiction boats prominent there, and familiar speed record-holder and painter’s names from the American powerboat world. Even on a sailing vacation, horsepower finds kindred spirits. Pirates Bight, however, with its new bright blue roof and striking white architecture, stole the show. We enjoyed the comfortable furnishings and excellent menu of the sophisticated beachfront restaurant with excellent service and a calmer vibe.