Foxy: Inside Scoop on a BVI Icon
I’ve known Foxy for many years, and he is as charming as his reputation implies. I have been to many of the events that he and his wife Tessa have hosted over the years from the Wooden Boat Regatta to his 80th birthday party and multiple music fetes. Each event was flavored with Jost Van Dyke magic and Foxy’s brand of impish charm.
Without a doubt, there are few BV Islanders as emblematic of the BVI’s barefoot Caribbean lifestyle than Foxy Callwood. He is as unique as the island on which he was born. A small mountainous island with only a few hundred year-round residents, Jost Van Dyke has one main road, a classic Caribbean church, primary school and numerous sand-in-the-toes beach bars – prime among them, Foxy’s Tamarind Bar. Located on a long stretch of sand on the eastern most end of Great Harbour, Foxy’s events are internationally renowned. Their New Year’s party and Foxy’s Wooden Boat Regatta, have put Jost Van Dyke firmly on the nautical map. A host of other events include Foxy’s Cat Fight (open to catamarans), the accompanying Masked Ball, both on Halloween weekend, and monthly full moon parties.
His charisma and creative spirit have brought Foxy a long way from the modest West Indian house in which he was raised. Over the years he has beguiled multiple generations of sailors as well as the many day trippers arriving by ferry with his barefoot nonchalance.
A natural restauranteur and barman, Foxy slid into the hospitality business with ease. He opened his first bar on Great Harbour just down from his present location in 1968, and expanded to his present open-air restaurant on Great Harbour’s eastern end a few years later. It was a free and easy time, and yachtsmen flowed into Jost Van Dyke as easily as rum poured into a glass. Their boats 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.
The Wooden Boat Regatta was the bar’s first major event. It was launched in 1974 when a group of Foxy’s 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. Over the decades, it became one of the BVI’s biggest sailing events, attracting not only racers, but hundreds of party-goers who arrived by boat and ferry to enjoy music and the event’s famous barbecue. One of the most memorable Wooden Boat Regattas I attended featured a wooden model boat race in Great Harbour. My kids brought their own homemade boats, joining dozens of Jost Van Dyke kids joyfully sailing their hand honed crafts.
Today with fewer wooden boats afloat, the event is smaller, and with the popularity of catamarans in the region, Foxy’s Cat Fight and Masked Ball, is now one of Foxy’s premier racing events. The New Year’s party (or Old Year’s Night party as it is referred to) has also become a must-do event for visitors and yachtsmen. The night features local and regional bands and a barbecue on the beach, while the upstairs room, “The Upper Crust”, features high end service, food and a lofty view of the proceedings.
Sitting in the bar on a tall stool, Foxy developed a reputation for satirical calypso renditions that would take jabs at local and international politicians and world events. Customers, who lapped up his jaunty tunes and tales, often became the subject of his barbed wit as well – all in good-natured fun that cemented Foxy’s reputation among the yachting community and further afield. Now in his 80s, Foxy sings less, but still mingles with his patrons, sharing quips and stories of present and past times.
Foxy’s – a far-reaching enterprise that encompasses two restaurants, a boutique and countless activities – is a family affair. Foxy and his wife Tessa met in 1971 on a Transatlantic sail from Europe. Over the years, the spirited Australian-born Tessa has been active in running the business and helping to organize and promote its many events. The couple’s daughter Justine (they have 3 children together) and son Christian currently live on Jost Van Dyke and help in the business. Another of Foxy’s sons, Dean, also assists as a DJ.
Featuring an Italian chef, and serving lunch and dinner, Foxy’s is far more than a Great Harbour beach bar. There is a tropical boutique, well-loved by boaters and visitors, a music school for island children and a second restaurant, Taboo, at Diamond Cay on Jost Van Dyke’s eastern end.
The couple is dedicated to raising environmental awareness, and one of their important achievements is the Jost Van Dyke Preservation Society. The organization focuses on historical and environmental conservation and restoration, and promotes environmental education among the islands’ school children.
In 2006 Foxy was awarded an MBE (Member of the British Empire) by Queen Elizabeth II for his community and environmental projects, as well as his role in promoting BVI tourism. Foxy attended the ceremony – a Caribbean free spirit, with a world following.
Foxy’s influence can be seen further afield. Tell people you are from the BVI and they will inevitably say they have been to Foxy’s. On a boat trip along the Chesapeake Bay in the US a few years ago, I came across a restaurant called Foxy’s – either a cheeky theft of his name, or a homage to the “Fox’s” wide flung reputation and admirers.
For more info on Foxy’s Bar and upcoming events, including the 2022 Old Year’s Party and the 2023 Foxy’s Wooden Boat Regatta, as well as other races and events go to:
