Sailing Through the British Virgin Islands

July 30, 2019

On the morning of Friday, April 4, the waters of the Sir Francis Drake Channel, which runs through the heart of the British Virgin Islands (BVI), will be teaming with cruiser-racer and bareboat sailboats, all waiting for the blast of an air horn and wave of a flag that signals the start of the 43rd Annual BVI Spring Regatta. The captains aboard the boats will have their sails set and bows pointed to cross the starting line and gracefully carve through the Caribbean’s stunning cobalt waters. Several races will stretch over the next three days, but for many, the fun starts five days earlier at Nanny Cay Marina on Tortola when the annual Sailing Festival begins and the party scene kicks into gear, fueled by a generous helping of painkillers, the signature rum-based drink of the BVI. 

As sailing events go, the regatta and festival may just be the most democratic and accessible in the world. It has something for everyone from America’s Cup and Olympic sailors to neophytes who want to give competitive sailing a try and even for people just looking to enjoy those painkillers and hitch a ride on a boat. The attraction: The BVI’s geography makes it a veritable theme park for the sailing set.

Warm Water, Hot Sailing 

The British Virgin Islands’ archipelago consists of 60-odd islands nestled between the Atlantic Ocean and the Caribbean Sea, about 70 miles east of Puerto Rico. Christopher Columbus came across this collection of long-dormant volcano remnants in 1493. Notorious pirates such as Sir Francis Drake, Blackbeard and Black Sam Bellamy, credited with capturing 53 ships in his day, all sought refuge in the numerous coves and anchorages hidden throughout the BVI during their careers.  Fast forward to 1972 when members of the BVI Hotel and Tourist Association decided to put on a regatta to bolster the growing recreational sailing community.

One of them, Peter Haycraft, served as the regatta’s chairman for 25 years and has the distinction of sailing in every race to date. It started off small, consisting of roughly 20 boats; mostly tiny one- or two-person boats such as Squibs and Sunfish racing between islands over the course of a weekend. This year more than 3,000 people will flock to the Sir Francis Drake Channel for the Regatta and Sailing Festival, with 125 boats expected to participate. What draws them? Phenomenal sailing in an incomparable setting.

“We’re very fortunate to have constant trade winds and fair seas,” says Judy Petz, director of the BVI Spring Regatta. In late March and early April, when it’s still frigid in much of the northern hemisphere, the BVI enjoys days with temperatures in the 80s (F), but the sea breeze keeps it comfortable. That same breeze blows steady through the islands, which form a protective circle around the waters between St. John to the west, Tortola to the north, Virgin Gorda to the east, and a string of close-together islands to the south. The Drake Channel, a deepwater straight that’s roughly nine miles long and four miles wide, runs between Tortola and the southern chain and bisects the territory. In all, the BVI offers nearly 60 square miles of nautical paradise.

For the week of March 31 through April 6, the spiritual home of island sailing sets up on the docks of Nanny Cay Marina, just west of Tortola’s main city, Road Town. By 6 p.m. on that Monday, the docks will be shaking from the good vibrations of a reggae backbeat, as the first Mount Gay Welcome Party kick-starts the week’s festivities.   On Tuesday morning you can participate in the Round Tortola Race, which doesn’t earn points in the regatta but is a cherished part of the weeklong festival. Boats that enter are trying to win the Nanny Cay Challenge for the fastest sailing time around the island. (The current record is 3 hours, 29 minutes, 41 seconds.) There’s another “pre-race” race for fun on Wednesday that ends in a beach barbecue. On Friday, with the start of that first official regatta race, it’s game on.

Sailing’s Caribben Open 

Fortunately, you don’t even have to know your spinnaker from your jib to take part in the BVI Spring Regatta. “There are all kinds of people involved, from Olympic and America’s Cup competitors to people who have never been on a boat before,” Petz says, going on to point out that the event has drawn competitors from as many as 17 different countries including the U.S., Canada, Italy, China and Croatia.

In all, there are 16 classes of boats that race in three different areas throughout the islands. Because the water is so protected—and land is almost always on the horizon—sailors rarely find themselves in adverse situations.  Experienced sailors without their own vessel typically charter a race ready bareboat, which is the equivalent of renting a car from the airport: You pick it up, sail off and return it when you’re done. It’s a family sailboat, with no crew or captain provided, and no spinnakers (the big billowy sails that are used to sail downwind). Most charters start on Tortola, the most populous island and the home of the international airport. 

“The BVI is a great place to try your first regatta,” Petz says. “It’s very relaxed and many of the boats are a lot smaller, maybe 40–50 feet.” With an experienced captain, it’s a safer endeavor, and you can bring along some of your own crew and participate as much as you want, from learning how to work the sails and man the tiller to simply moving from one side of the boat to the other to maintain the proper keel angle (the way the boat leans as it glides through the water).  

Depending on the boat’s size, a crew consists of anywhere from two to 22 people. If you don’t want to charter an entire boat, there are ways to sign up to be a part of someone else’s crew, with spots available for any skill level from novice to expert. After the last race on Sunday, everyone makes their way over to Regatta Village on the beach at Nanny Cay for the awards ceremony where the winners pick up their trophies and relive their experiences, while the revelers try to remember theirs.

 With first, second and third place prizes given out for all 16 classes, there’s plenty of love to go around, starting with the winners who pick up bottles of champagne or top-shelf rum and quickly disseminate it to their crews. It may be the only time all week where a captain’s shout, “Bottom’s up!” is met with a cheer instead of fear.

Sailor’s Paradise 

The same characteristics that make the BVI ideal for a regatta make it easy for newbies to give cruising a try. For one, it’s hard to get lost. “It’s mostly line of sight sailing,” says Bob Friel, the former editor in chief of Caribbean Travel & Life magazine about the friendly confines of the Drake Passage. “It works for sailors of any experience level.” “Every day you’ve got a pretty straight forward plan,” Friel says. “You wake up in a gorgeous anchorage with a beach bar and sail to another gorgeous anchorage with a beach bar.” Many charter companies such as Palm Yacht Charters offer three-day sailboat charters that give you a taste of the island cruising life. Or opt for a day-cruise outing that involves snorkeling, island hopping and a stop at a popular restaurant or beach bar.

The bars of the BVI are stuff of legend, starting with the Soggy Dollar Bar in White Bay on Jost Van Dyke. Set back from the white sand beach in a canopy of palm trees, the Soggy Dollar earned its name from patrons paying for their drinks with wet money from swimming in or falling off their dinghies—there’s no dock so you have to anchor off the beach. The Soggy Dollar lays claim as the home of the original painkiller. Just around the corner in Great Harbour, there’s Foxy’s Bar. The key is to go in the daytime and hope the legendary proprietor, Foxy Callwood, is performing. Callwood has called himself the laziest man on earth, but his bar and musical performances have attained cult status. “He’s the most famous raconteur in the BVI and will make up a song about you and your crew on the spot,” Friel says. Those lucky enough to earn an original composition leave with some of the same sailing street cred attained from a weathered Mount Gay hat. 

If bar-hopping BVI style isn’t your style, book one of the best dives in the entire Caribbean, the wreck of the Rhone, a British mail ship that sunk during a hurricane in 1867. Pirate enthusiasts and literary types can investigate Norman Island, the place that reputedly inspired Robert Louis Stevenson to write Treasure Island. Or cruise over to the natural wonder of The Baths on Virgin Gorda, where giant boulders along the beach trap secluded pools of water. And there’s the Bitter End Yacht Club on Virgin Gorda, perhaps the most well known sailing destination in the  BVI with its sheltered North Sound, an ideal playground for small boats.

A Personal Vacation Advisor’s Must-Do List

Beach: The best is going to be the sugar-white sand and aqua-blue waters of Cane Garden Bay on Tortola. 
Eat:  You can’t beat the local flavors of the Banana Keet Café located in the hills above Cane Garden Bay  
Spa: At Serenity Spa inside Sopers Hole Marina, they’ll pamper you with everthing from massages and facials to yoga and acupuncture. 
Day Trip: Hop over to Virgin Gorda and explore The Baths, a collection of giant boulders along the beach. It’s the BVI’s signature natural wonder and photo op.