Rum, Regattas, and Resilience: Tortola’s West End Yacht Club

Tucked into the quiet southwestern tip of the island, Tortola’s West End and adjacent Frenchman’s Cay offer a different pace of island life.  While Roadtown buzzes with commerce and cruise ships, the West End, despite being a well-worn waypoint for travelers and locals alike, feels unhurried.  Fringed by a ferry terminal on one side and the candy-colored cottages of Soper’s Hole on the other side of the harbour, what makes the area special isn’t just that it’s picturesque; it’s the sense of arrival.  Whether you’re disembarking from a boat or cruising in by car, the West End feels like the threshold between land and sea.

Connecting Tortola and Frenchman’s Cay is a little ribbon of land known as “The Sand Spit”, which is home to the West End location of Omar’s Fusion Cuisine, a local restaurant serving a fusion of East Indian and Caribbean (West Indian) food. Pull up your dinghy up and head to Omar’s for happy hour, where you’re likely to meet one of the members of the local yacht club: the restaurant’s West End location doubles as the West End Yacht Club’s “clubhouse.”

History  of the West End Yacht Club

Founded in 1978 by a group of sailors who frequented Soper’s Hole, the West End Yacht Club began by meeting casually at Walter’s Superette on Frenchman’s Cay.  In friendly rivalry with the established Royal BVI Yacht Club, former West End Yacht Club Vice Commodore Robin Pinfold coined the tongue-in-cheek moniker “Loyal” West End Yacht Club, which stuck.

Initially based at Nanny Cay, the club relocated to the Jolly Roger Inn in the early 1990s, where it remained as a home base until the property was destroyed by Hurricanes Irma and Maria in 2017. Since then, Omar’s West End location has served as the club’s base, hosting shoreside activities and race awards. Despite hurricanes and other challenges (like border-closing pandemics), the club’s tradition remains steady: to host fun, friendly and inclusive sailing events that bring together locals, cruisers, and visiting yachts from around the world.  Every West End Yacht Club regatta follows a proven recipe: one part race, one part after-party.

Here’s a look at WEYC’s annual calendar of events:

Foxy’s Halloween Cat Fight

Launched in the late 1990s, with local legend, Foxy Callwood, this multihull-friendly race coincides with Halloween weekend. Costumes are encouraged (both onboard and at the after-party), and all vessel types are welcome (including monohulls and trimarans). The 2025 event is set for Saturday, November 1^st, in Great Harbour, Jost Van Dyke. Foxy’s Tamarind Bar hosts live music for the event.

Gustav “Ding Dong” Wilmerding

This race takes inspiration from the possibly mythical pirate Gustav Wilmerding said to have made Little Thatch Cay his base.  As the legend goes, his band of pirates raised such a ruckus upon returning from their plunders that the local islanders would loudly ring bells announcing the return of the ships, laden with stolen booty, thus Gustav’s notorious nickname “Ding Dong.” The club admits that the tale is probably fictitious, but the story calls for bells, booty, and merriment, which is a great way to ring in the holiday season. The 2025 race is scheduled for December 7, 2025 and includes a ruckus-raising after-party at Omars on the Sandy Spit.

Sweethearts of the Caribbean Regatta

Launched in 1981, this race occurs around Valentine’s Day and was developed to pay tribute to the romance of the sea and the timeless beauty of classic sailing vessels, especially the schooners that were once prolific. The next Sweethearts of the Caribbean Regatta will take place on February 14, 2026. All boats are welcome to participate.

Dark and Stormy Regatta

Named after the iconic rum cocktail, this three-day event combines competitive sailing with shoreside activities on Anegada. Held at the height of trade wind season, the regatta features a pursuit race from Trellis Bay to Anegada, a weekend of island festivities, and a return sail to Tortola. The 2026 event is March 7-9, during a Virgin Islands holiday weekend.

Foxy’s Wooden Boat Regatta

 Foxy Callwood and West End Yacht Club’s celebration of traditional wooden sailing craft occurs annually on Jost Van Dyke.  Wooden boats, and especially island sloops, are an important, albeit dwindling, part of the maritime heritage of the Virgin Islands.  In 2025, some of the existing wooden boats were too damaged to sail. West End Yacht Club Commodore, Steve Varrow, stepped in and initiated a fundraising campaign, which raised more than $5,000 for the Tortola Sloops “Youth Instructor” and “Intrepid” to help ensure that racing and important maritime traditions were kept afloat.  The 2026 regatta is scheduled for May 23-24, 2026. You don’t need to have a wooden boat to participate: all vessels are welcome to participate.

Firecracker 500 Regatta

Americans visiting the British Virgin Islands in July may miss the 4^th of July festivities, but thankfully, the Firecracker 500 lights up the Little Thatch cut with colourful spinnakers during this one-day regatta scheduled for July 4, 2026.  Adding a bit of Americana to the event is the “Chilli Cook Off”, which brings amateur and professional chefs together to compete for the title of best Chilli during the Awards ceremony and after-party at Omar’s on the Sand Spit.

Learn More
Membership is open to all, inclusive of visiting sailors. At just $50 to join, it may be one of the best deals in the Virgin Islands, complete with club swag and discounts on food and drink at the “Clubhouse.” You can learn more by visiting www.westendyachtclubbvi.com.