North Soundings | The Caribbean Regatta that Could

How the Pro Am Put BVI Racing on the Map.

In 2016, the Pro Am Regatta celebrated 30 years of pairing professional athletes with amateur and first-time sailors in a thrilling series of races across North Sound. In these three decades, the Pro Am has grown from a local party to an internationally renowned event that attracts World Champions, Olympic medalists, sailing legends and even supermodels. As we reflect on this major milestone, BEYC founding family member Richard Hokin revisits how the world’s most unique regatta got its start.

Shortly after we acquired Bitter End in the early 1970s, I proposed that Bitter End sponsor an annual race from St. Thomas to Gorda Sound. This event resulted in a robust turnout of BVI and USVI sailors, who seemed to be motivated to sail upwind to Gorda Sound by the prospect of a raucous party and open bar in the Clubhouse. This was great fun for the local sailing community but did little to broadcast the message that the BVI, and Gorda Sound in particular, was a great venue not only for leisurely cruising but also for competitive sailing. Back in those days, the combination of 100+ thirsty sailors and an open bar was a financial disaster for a resort with a mere handful of rooms.

By the mid 1980s, the resort had added a number of beachfront cottages to the original hillsides, expanded its waterfront infrastructure and was in the process of integrating the neighboring resort, Tradewinds, into its footprint. All this made Bitter End a much more compelling destination for resort guests and expanded our opportunities to utilize the potential of Gorda Sound as a first-rate venue for competitive sailing.

Meanwhile, although the St. Thomas to Gorda Sound event had faded away, I had become much more deeply involved in serious yacht racing. For about ten years, beginning in the mid-1970s, I was heavily into hardcore offshore sailboat racing, starting with a series of five boats called Love Machine and winding down with Cosmic Warlord, an Express 37 that continues to spend her golden years on North Sound. The success of this endeavor came from having a great crew, from bowmen to pitmen to helmsmen. Among the central characters were sailing rock stars like Tom Whidden and Peter Isler, backed up by many great, albeit lower profile, sailors. One of the stalwarts of our crew, the late Steve Surprise, a.k.a. Roundman, later became a BVI icon.

The Bitter End Pro Am evolved out of my obsession with sailboat racing and the addition of John Glynn to BEYC’s crew. My dad had met John at the resort. At that time, John was an editor at Yacht Racing magazine who had favorably mentioned Bitter End in print. That John “got” what it was all about warranted immediate elevation to Myron’s A-list and a job offer. John brought with him not only great enthusiasm for boats, sailing and the accompanying lifestyle, but also a great network with the sailboat racing community. Kicking around the idea of a new competitive sailing event at the resort made us realize that involving the resort’s rank and file guests needed to be the centerpiece of anything we came up with—and that’s how the idea of a Pro Am format was born. Now, we just had to figure out how to fit the event into the annual schedule so that we could attract both pro and amateur sailors while raising Bitter End’s profile in the competitive sailing community.

The autumnal equinox seemed to be the critical point in the scheduling decision. The month or so following it had two important features: the wind-down of the North American sailing and regatta season, and the emergence of the Caribbean from the annual torpor and unsettled weather that bracket the equinox, which brings a fresh new season with revitalized breezes to the BVI. What better time to hold the event than when North American sailors of all stripes were yearning for anything to prolong the sailing season, and a venue was offering its own version of spring about six months ahead of the temperate climate zones?

Perhaps the most significant factor in the Pro Am’s success was John’s genius not only in recruiting the pros, but also in convincing a bunch of ruthless, bloodthirsty and intensely focused competitors that—win or lose—this was going to be a fun event for all involved, including them. That has become the regatta’s trademark. It’s hard to imagine an America’s Cup skipper, tactician or designer tolerating a bunch of hackers for crew, but they do and usually with a smile. The proof: pros and amateurs keep coming back for more.

Nothing characterizes the spirit of Bitter End’s Pro Am more than something I witnessed one year when Buddy Melges was among our pro skippers. During one race a member of Buddy’s crew failed to duck during a jibe and ended up with a nasty deep gash across his forehead. Buddy’s crewmember was quickly transported to the Virgin Gorda clinic, where micro suturing was not an option. The injured crewmember made it back to BEYC just in time for the post-race cocktail party with about six inches of shoelace-like stitches—he couldn’t have been more ecstatic about his prospects for a Frankenstein-style scar across his forehead. “I can’t wait,” he said, “to tell the guys at my yacht club bar that I got this sailing with Buddy Melges.”

The 30th anniversary of the Pro Am Regatta was a week-long event held October 22-29, 2016. The event was presented by BVI Airways.

For more information on the participating in future Pro Am Regatta’s, click here


Most wins in Pro Am history: Ed Baird, with seven wins in 30 years. He was at the very first Pro Am, and he returned again in 2016.

Number of supermodels to race Pro Am: 1, Heidi Klum, as part of a Sports Illustrated Swimsuit Edition photoshoot

Number of Pro Am races cancelled or postponed due to lack of wind: 0 of almost 500 races run

Number of Pro Am races shortened due to lack of wind: 3 of almost 500 races run

Estimated number of “Am” guests who have attended/participated in 29 years: Approximately 900

Number of Pro Skippers who have participated: 51

Number of Mount Gay Red Hats given in 29 years: 1600 Many of the 900 AM guests repeat year to year.

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