Foxy’s Famed Wooden Boat Regatta
by Claudia Colli
Whether you are a sailor, or a veteran party-goer participating in the famed post-race celebrations, the 2026 Foxy’s Wooden Boat Race, is not to be missed. This year, registration will be held at Omar’s Sand Spit at Frenchman’s Cay, Tortola on Friday, the 23rd, while racing starts the next day, Saturday, May 24th. Boaters will race to Jost Van Dyke where they will overnight at Foxy’s in Great Harbour for the troubadour’s legendary barbecue, music and party atmosphere. Then on Sunday, there will be a day of great racing followed by an awards ceremony and another fun evening of partying on Sunday, the 25th.
There are few races as emblematic of the BVI’s carefree racing scene as Foxy’s Wooden Boat Regatta. First launched in 1974, the regatta was the inspiration of Foxy Callwood, the celebrated Jost Van Dyke bar owner, calypsonian – and along with his wife Tessa – force behind some of the BVI’s most iconic parties.
Foxy Callwood is as unique as the island he was born on. A small mountainous island with only a few hundred year-round residents, Jost Van Dyke, has one main road, a classic Caribbean church, a primary school and numerous sand-in-the-toes beach bars, prime among them, Foxy’s Tamarind Bar. Located on a white sand beach on the eastern most end of Great Harbour, Foxy’s events are internationally renown. Its Old Year’s Eve party, reputed to be one of the world’s top new year events, Foxy’s Catfight and Masquerade Ball – and Foxy’s Wooden Boat Regatta, have put Jost Van Dyke firmly on the nautical map.
A Jost Van Dyke native, who grew up in a wattle and daub house, Foxy has charmed multiple generations of sailors as well as the many day trippers arriving by ferry. A natural restaurateur and barman, Foxy slid into the hospitality business with ease, opening his first bar at the dawn of the free and easy 1970s when yachtsmen flowed into Jost Van Dyke as easily as rum poured into a glass.
The boats in those days were wooden, schooners, Baltic Traders and yawls, harking back to the romantic days of sailing. Owned by sailors with faces chiseled by hard sailing and years in the Caribbean sun, they sailed into Foxy’s from Tortola, St. John and St. Thomas to drink with “The Fox” and listen to his salty stories of island life. Foxy would entertain with mischievous calypso songs composed on the spot, often spoofing his international coterie of customers.
Legend has it that a group of his regular customers, intent on proving their sailing chops, cooked up the first Wooden Boat Regatta over rum and beer. Less than a dozen or so boats sailed in the first regatta, but the after party was awesome and as word got out, more joined the ranks each year.
Not racing? No worries. In addition to the racers, hundreds of party goers are expected to flock to the island by sail boat and ferry to enjoy this classic event, Foxy’s and Tessa’s famous barbecue, live music and good vibes.
For more race info go to the BVI West End Yacht Club’s website Notice Blog at:
For more info on Foxy’s Bar go to:
