Type to search

BVI’s Sailing History with Island Icon, Foxy Callwood


While most people who have ever dropped anchor in the Caribbean have heard of Foxy, not everyone knows the history of his life and his bar, which parallel the history of sailing in the BVI.

After 50 years in the BVI beach bar business, “Foxy” Callwood has become a local legend in the Caribbean and an island icon in the sailing world. He has spent the entirety of the 80 years of his life on the tiny island

of his BVI birth – Jost Van Dyke – where he owns and operates his namesake “Foxy’s Tamarind Bar.”

The only way onto or off of Jost Van Dyke is by boat, and for fifty years, this barefoot troubadour has been quick with a joke, song or story, entertaining the countless visitors who come ashore. His infectious smile and welcoming attitude have made him the perfect host – and he has unofficially been dubbed “the ambassador of BVI tourism.” He has also received numerous official awards for his contribution to heritage, tourism and the yachting industry.

These include induction into the Charter Yacht Broker Association’s Charter Yacht Society Hall of Fame (Antigua, WI) and investiture as a MBE (Member of the Most Excellent Order of the British Empire), awarded by H.M. Queen of England in recognition of his contributions to culture and tourism in the British Virgin Islands. ‘

Celebrating BVI Sailing’s Silver Anniversary at the 2018 United States’ Sailboat Show

It’s a warm autumn day on the Eastern Seaboard, and Foxy Callwood is wearing his signature grin, a t-shirt emblazoned with the name of his own bar. He is, of course, barefoot. With a guitar slung over one shoulder, he is making his way along the docks of Annapolis’ historic waterfront. The crowd is thick, but people frequently stop to greet Foxy, surprised to see the infamous islander. It’s a sailing town, and it’s no surprise that here, Foxy is a celebrity.

Foxy attended the 2018 Annapolis’ United States’ Sailboat Show, an annual event which the sailing world perennially recognizes as the largest and most prestigious sailboat show in the world. The event is critically important for the Caribbean’s booming charter yachting industry partners and many Caribbean-based companies attend the show faithfully working to woo sailors to their West Indian homeports with the promise of sun-drenched, rum-infused and sea-soaked holidays. Two of the 2018 show’s major sponsors are household BVI names: the BVI Tourist Board and The Moorings Company. The BVI is often recognized as the Sailing Capital of the Caribbean; and at this event, the relationship between the BVI and sailing is an obvious one.

The atmosphere for BVI businesses at the boat show for 2018 is a celebratory one, and a radical shift from the morose mood at last year’s event, in October 2017. The BVI Yachting industry was still heaving from the impacts of two record-breaking Category 5 storms, Hurricanes Irma and Maria. The storms delivered a punch that totaled nearly 90% of the Territory’s yachts, and in the immediate aftermath of the storms, this blow seemed nearly fatal. Pessimists guessed that it could take years for the BVI’s tourism industry to bounce back, and it seemed like yachting suffered the most. Despite the initially gloomy projections, only a year after a major catastrophe, most industry partners are reporting full bookings for the upcoming 2018/2019 sailing season.

Whirling in the renewed remembrance of the importance of sailing to the BVI following the BVI’s post-Hurricane revival, Foxy attended the Annapolis show to re-connect with tourism partners. Along with the Moorings Company, Foxy’s namesake “Foxy’s Tamarind Bar” is celebrating its 50th year of business – again underlying how Foxy’s history is a part of the genesis of BVI sailing. During the show, Foxy performed at a Moorings reception on board one of their brand new Leopard 50 catamarans, recounting his early memories of sailing – and The Moorings.

The 1960’s: A simple splash into the sailing world

In 1966, a young (and enthusiastically entrepreneurial) Foxy Callwood built a small bar – “Mom’s Booth and Foxy’s Bar” to sell drinks for $0.25 a piece on the tiny British Virgin Island of Jost Van Dyke for the island’s annual Harvest Festival hosted by the Jost Van Dyke Methodist Church.

A visiting sailor from St. Thomas approached the young Mr. Callwood at his original ‘booth’. Along with her husband, the woman operated a sailing yacht out of St. Thomas and struck an agreement with Foxy—she would bring visitors onboard her sailboat if Foxy would provide drinks and a little entertainment with his guitar. Foxy obliged and in 1968 set up a permanent establishment further down the beach at the eastern side of Great Harbour, where Foxy’s Tamarind Bar remains to this day.

In the early days, Foxy glimpsed the future in visiting vessels and wanted to cater to and welcome this group of visitors. “The start was slow,” says Foxy, as he describes his first year and the frequency of visiting yachts to his home port of Great Harbour. “But I never set out to make money, just to have fun,” he states, remembering the early days fondly.

According to Foxy, “All of a sudden, I started seeing these boats coming around every week – about 6 or 7 of them,” he reminisces. According to the Moorings, the company’s original owners Charlie and Ginny Cary pioneered yacht chartering in the BVI by opening operations on Fourth of July weekend, 1969 with a sailing fleet comprised of six (6) 35-foot Pearson yachts.

Foxy was grateful for the boat traffic to his burgeoning bar business and he wanted to thank the people responsible so he set out in Tortola to find The Moorings’ Office on Tortola, armed with what he describes as a “nice king fish I had caught.”

He presented Charlie with the Kingfish who, Foxy notes with an impish grin, “didn’t know what to do with it.”

“So I cut it up for them and they told me that I might as well stay and help them eat it. So we ate and we drank wine. We had a good time late into the night and they invited me to spend the night there with them. So that’s how it started and that’s how I came to know Charlie and Ginny Cary and the Moorings Company.”

The 1970’s: How Sailing helped Foxy find his ‘first mate’

Among the stories in Foxy’s mental treasure chest is the tale of how the sailing world helped him find his wife, Tessa. The saga begins with Foxy, as a young island bachelor who would be ‘overly friendly’ to pretty cooks onboard visiting sailing vessels. Foxy still has a mischievous twinkle in his eye, and it’s not hard to imagine young women temporarily abandoning their onboard posts for a romantic tryst onshore a tiny tropical isle with a younger version of this charming man. As part of an effort to thwart cooks from abandoning ship, one captain and friend, Bill Bodle, reportedly shanghaied Foxy, taking him on board his schooner, Nordlys, with the hopes of helping Foxy to find a bride in 1971.

Foxy typically relays this story in a lyrical poetic form. As if you’ve just stuck a quarter in a jukebox, Foxy will crank to life, relating a trans-Atlantic sailing voyage and then rattling off a list of European locales where he went searching for a bride. Despite his quest, the young Foxy returned to Gibraltar to board Nordlys for his return voyage to the Caribbean, alone. It was not until the young Foxy was back in the bosom of sailing that he found “her”- a feisty young Australian, named Tessa, who boarded Bill’s boat bound for adventure in the Caribbean.

Married for more than 40 years, Foxy and Tessa have 3 children together. Tessa has gone on to help build one of the most successful brand names in the Caribbean and has become a legend herself in the retail world of West Indian merchandising.

The 1980’s and 1990’s: The Prince of Parties.

The name Foxy has become almost synonymous with parties over the years. In the 1980’s, bareboat charters took off, and as the industry rocketed to success, Foxy’s became known as the host with the most and his bar became the ‘it’ destination for sailors everywhere.

While the bar often uses the tag line “where every day’s a party.” One party is a standout. For decades, Foxy’s Tamarind Bar has led the charge in hosting Jost Van Dyke’s Old Year’s Night /New Year’s Eve Celebration. The party was always popular but the mayhem mounted to epic proportions for the Millennium.

In 1999, the world was still stewing over the “Y2K bug” and fears that this cyber coding glitch would create impending havoc on the computer systems across the globe once the clock struck midnight on January 1, 2000. Somehow, the global media caught wind of Foxy’s epic event and the appeal of being on a tiny barefoot paradise – away from places like London or New York City hit its moment of fame.

International media began to cover the out island event, which quickly became named as one of the top 5 places in the world to spend New Years’ Eve- and has remained at the top of the list ever since. The party is still wildly popular, drawing in thousands of revelers and the harbor fills with hundreds of boats, ranging from tiny sailboats to massive megayachts.

While the annual New Year’s Eve (Old Years’ Night as it is known in the Caribbean) event may be the largest party, Foxy has also been a keen obverser of trends in BVI yachting and has also cultivated some of the best sailing events in the region.

Wooden boats and windjammers were the original backbones of BVI bar business, but even by the early 1970s, wooden vessels were being replaced with more modern fiberglass vessels. Most regattas in those days were for sleek new fiberglass vessels. Foxy still had a lot of friends with wooden boats and in 1973 he created “Foxy’s Wooden Boat Regatta” with the West End Yacht Club. Initially held during Labour Day weekend in September, the number of participating boats swelled to nearly 100 in some years.

In 1989, Hurricane Marilyn smashed into the Virgin Islands, sinking many of the original participating wooden yachts and scattering sailors away during September. The race was moved to Memorial Day and although it continued until 2017, it never rebounded to its original level due to a lack of classic vessels. Despite the smaller size, the event is well esteemed in the world of wooden boats.

In 1996, Foxy also recognized the potential rise of catamarans in the BVI’s charter industry and wanted to create a race to “see what these ‘new’ boats could do. Joining forces with Tortola’s Loyal West End Yacht Club, Foxy’s Cat Fight, the Caribbean’s first multi-hull regatta, was born. The spirited event has taken place annually on the weekend closest to Halloween. The cocktail of success for any BVI regatta is to blend up one part race with one part party, and Foxy’s Cat Fight is no exception. The event’s after-party is a Masquerade Ball, and goblins, ghosts, witches and wenches all pack themselves onto Foxy’s dance floor after a day on the water. The event was canceled- for the first time since its inception in 2017 due to Hurricane Irma, however, just one year later the race was back on and in 2018 was the BVI’s second-largest regatta, following the BVI Spring Regatta.

The 2000s and beyond: BVI Preserving the Past of the BVI’s Maritime Heritage

Foxy has always been a proponent of supporting cultural traditions in the BVI. In the 2000s, he worked to set up the Jost Van Dykes Preservation Society, a non- profit group, to help preserve nature and heritage on Jost Van Dyke. One of the Society’s flagship projects has been the building of Endeavour II, a wooden sailing vessel, which bears the unmistakable lines of a Tortola sloop.

The boat was built with shipwrights and aided by local youth laborers from Jost Van Dyke. Launched in 2013, the vessel was used to rekindle maritime traditions and used in the Preservation Society’s annual summer program for local youth to learn about sailing and maritime traditions. The vessel survived Hurricanes Irma and Maria, but was badly damaged and will be under-going repairs into the spring of 2019.

Numerous visitors to Foxy’s helped pitch in to build this special boat, which was constructed entirely in the backyard behind Foxy’s Bar in Great Harbour. Among the most noteworthy of large donors was Grammy Award-winning musician Kenny Chesney. The country singer has strong ties to the Virgin Islands and is a frequent visitor to Jost Van Dyke. In 2018, the musician released a new album, “Song for the Saints” proceeds of which go to benefit Virgin Islands’ Hurricane relief. The album’s cover depicts Endeavour II at anchor on a calm day.

Foxy Callwood: A Charmed Life

In his early days as a host and entertainer, the sailing world came to Foxy. The captains and crews onboard became part of an ever-expanding network of friends, who are today part of a global grid, which still hold Foxy in high regard. When asked what is so special about Foxy’s, someone once commented,

“It’s like a virtual yacht club.Go anywhere in the world and spot a Foxy’s hat or t-shirt and you’ll find yourself swapping sea stories with another sailors, as if you’re old friend.”

The best part is that there is no membership dues or requirements to be a part of Foxy’s Club. Just come on by the Bar, he’ll be waiting with a drink – and a smile.


You Might also Like