Sailing the British Virgin Islands remains one of the most iconic boating experiences in the Caribbean, even after the devastating impact of Hurricanes Irma and Maria.
Text & Photos by Marilyn DeMartini
We had just locked in the coveted hotel room for our annual pilgrimage to the Mecca of powerboating—the Offshore Powerboat Racing World Championships in Key West. Price gouging is alive and well on the island every November, but we swallowed hard and booked anyway. That’s what you do for friends and a little raucous celebration of speed.
Then the phone rang.
A longtime friend and seasoned adventurer dangled an irresistible alternative: “How’d you like to go sailing for two weeks in the British Virgin Islands? I’ve got a 45-foot cat chartered—and I have to use it in November.”
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While I stammered about Key West reservations, visions of turquoise water, white sand, and warm trade winds replaced the image of Duval Street. This wasn’t just any invite—this was from someone with a dozen BVI bareboat charters under his belt, including one memorable trip we’d taken together more than a decade ago.
A quick check with my hubby Dave—who hadn’t been to the BVI in 30 years—resulted in an enthusiastic nod. Why not trade overpriced hotel rooms and roaring engines for a real island escape?
There was only one caveat: We are not sailors.
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Navigation, sail handling, and plotting our course were officially assigned to “Captain Greg.” We promised to be excellent crew, contribute to provisioning Capriccio de Mare, which was neither “on the dock” nor open. His only question was, “Can you guys slow down and relax on this trip?”
Message received: Slow down. We agreed to try. Triple-digit miles per hour to single-digit knots—this should be interesting.
Why the British Virgin Islands Still Matter to Boaters
Approaching Tortola, I pressed my face to the plane window, snapping photos of azure water punctuated with islands, white sand, and boats—lots of boats. Clearly, we wouldn’t be alone.
Customs went quickly. Our luggage was light—bathing suits, flip-flops, books, and zero expectations. Finding our cab ride, however, was our opening lesson in “island time.” The first disheveled driver and car confidently delivered us to the wrong Capriccio de Mare which was neither “on the dock” nor open. After another $30 ride in an equally unkempt cab (following much debate among conferring locals), we finally reached the correct dockside restaurant and boarded what would be our home for the next two weeks: the 45-foot Lagoon catamaran, Sea Runner II.
Fully provisioned, we headed to Norman Island—alleged inspiration for Robert Louis Stevenson’s Treasure Island—and picked up our first mooring. Dinner was simple and perfect: grilled fish, potatoes, salad, music, and toasts to a new adventure. Stars overhead, water lapping gently against the hull.
Yes. We could do this.
Planning a BVI Charter: What’s Changed
The BVI have survived many storms, but Hurricanes Irma and Maria in 2017 were dramatically devastating. Once-familiar places felt new—some beautifully rebuilt, others left in ruins, and many replaced by polished resorts that brought a different energy and look to island life.
Moorings are now everywhere, designed to protect reefs from anchor damage and to manage the sheer number of boats. That also means reservations and fees via the new Boaty Ball app—functional, though not intuitive. Many moorings remain first come, first served, with morning or evening dinghy visits from fee collectors who also sell ice and collect trash. Convenience counts.
Pro Tip: Book moorings early using the Boaty Ball app during peak season (November-April).
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A Real BVI Sailing Itinerary
Cooper Island: Rum Bars and Beach Clubs
We snorkeled The Caves at Treasure Point—an ideal paradise warm-up—and later dinghied to Cooper Island Beach Club for lunch at the new Rum Bar, followed by a swim. Life slowed beautifully. Reading and resting ensued.
I could get used to this.
The next morning brought a reminder that paradise has teeth. Strong currents near a rocky snorkeling spot made the swim back to the boat feel far longer than expected. Advanced swimming skills—and respect for currents and rock-smashing tides—are nonnegotiable here.
At Marina Cay, we found a new bar and restaurant, a pictorial memorial to Our Virgin Island, the 1958 book and film starring John Cassavetes and Sidney Poitier. We also watched an e-foil demo at Up ’n Under Watersports that was equal parts hydrodynamics and balance. We bumped into fellow charterers we’d previously met and reunions recurred throughout the trip, all of us following similar island-hopping routes.
Trellis Bay: Full Moon Parties
En route to Trellis Bay for a Full Moon Party, a lucky dock opening landed us at the toney Scrub Island, now a full-scale Marriott resort with pools, spa, boutiques, and restaurants. One pool for kids with water slides was topped by another adult pool featuring an in-water bar.
Ahhh! We spent the day soaking and sunning, enjoying the bonus of meeting new friends from the U.S. performance capital, Lake of the Ozarks. The performance world is tight.
That night’s Full Moon Party delivered a spectacular buffet with steel drums, stilt dancers, bonfires and dancing under a brilliant moonlit sky. Golf carts ferried us back long after we’d lost track of time.
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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.
Final Days & Final Thoughts
Our final days included snorkeling at The Indians and a visit to Peter Island Resort & Marina. I remembered the luxury of the location, now fully transformed under the ownership of Amway Corporation executives, into a high-end resort with expanded marina, sports facilities, pools and elevated dining. Lunch at the Drunken Pelican impressed with thoughtful design, decor, furnishings, and private social settings. A sumptuous, romantic dinner at the hilltop Drake Steakhouse—complete with a chandelier table on the beach—was a flawless sendoff.
Returning to Road Town, Tortola came into view too soon. Laundry rules observed, bar leftovers gifted dockside, we headed home through Beef Island Airport with mixed emotions.
The trip was restorative: books read, swims logged, meals savored, friendships renewed. But it was also reflective. The BVI are more developed, more crowded, more discovered. Some native charm remains, but with the impressive newness comes a departure from the island ambience. Notably, serenity can be fleeting due to the sheer numbers of charters by The Moorings, MarineMax, and independent charter companies.
The islands still offer undeniable beauty and adventure, forever etched in my memory. Maybe the change is in the islands; maybe it’s in us. Or maybe it’s simply time to scout the next paradise, begging for discovery. bvitourism.com
Sailing the BVI FAQ
Is the British Virgin Islands good for beginner sailors?
Yes, the BVI are considered one of the best beginner-friendly sailing destinations due to short distances, line-of-sight navigation, and abundant moorings.
Do you need the Boaty Ball app in the BVI?
Yes, many moorings now require reservations through the Boaty Ball app, especially in high-traffic anchorages.
What is the best time to sail the BVI?
The best time is November through May, when trade winds are steady and hurricane season has passed.
