Hook-In-Hold-On began in 1979. It was dreamed up in a bar in St Thomas by Mark “Smitty” Schmidt who surmised it would be fun to set sail upwind to the British Virgin Islands aboard windsurfers. I was just getting into windsurfing then, and I still recall looking down from our house and seeing the racers streaking on a broad reach from Cane Garden Bay back to St Thomas.

In 1982 I competed in the event for the first time. Racing on a stock windsurfer, I remember being very overwhelmed at the beginning of the week of racing. By the end of the event, I nailed some decent finishes. The courses then were very long with 10-mile upwind legs. I recall the awesome Dutch racers charging upwind on their Dufour Wings. They all had custom sails—big white triangles. The Dutch also sported Speedo bathing suits and neoprene boots. Chest harnesses were high-tech then, and harness lines were ropes tied to the boom.

A standout memory of mine from the 1980s event was the incredible team effort. Besides the formidable Dutch, there were the Antiguans who would arrive on an enormous schooner packed with racers and gear. Big Puerto Rican teams were defined by their style—big boats, flashy gear, sexy women, and a champion named Kiko. One thing a Caribbean team always arrived with was rum. The Antiguans would have cases of Cavalier, the Puerto Ricans had Don Q, and Team Martinique brought Neisson which is perfect for drinking Ti Punch – basically, rum, sugar and lime.

The former Hook-In-Hold-On was last run in 1986. The event had stabilized itself to include only two classes: Open and Cruising. The board of choice was the Mistral Equipe, and a record 148 competitors sailed over 100 miles through the British Virgin Islands for a week. This was my second time in the event, and I made my mark by tying for first place with Austrian speed merchant Erich Maderthaner. I won the first race and then finished second in every other, except fatefully, the last, when I slipped to third in an agonizing downwind pumping session with my good friend Inigo Ross from Antigua. Maderthanner and I tied for first overall, and at the awards, event sponsor Pan Am offered up an airline ticket to Europe which I used to go to Spain to finish my last term of university.

Things changed when Johnnie Walker pulled the plug on their sponsorship in 1986. Wow, no more HIHO. It was a drag. Faithful participants still came down in the summer, rented charter boats, and retraced the event. The local windsurfing talent poured their energies into pro racing and national championships, and they flourished.

My 1986 win led to a short career as a World Cup journeyman. But needing to move on, I had the idea of resurrecting the windsurfing event I loved so much. In 1992, I obtained the rights to the HIHO name and formed a company called Ocean Promotions, and the event was reborn the following July.

With the new HIHO, I worked hard to be faithful to the roots of the event which I felt were the keys to its success. The simple formula was to combine a great trip through the islands aboard yachts with outstanding windsurfing racing. Superlative meals and entertainment were also a must. The first year was tough. The Moorings were helpful in offering us a complimentary yacht, and a gang of windsurfing friends came up from Aruba and Bonaire.

A couple years later, Bacardi Rum stepped up to the plate as title sponsor and the event’s trajectory took off. With TV money, the publicity was outstanding, and participation increased to as many as 90-racers in 1999.

One of my favourite accolades came back in the 1990s when a group of racers complimented us on how the race was run. An Italian participant said the food was great, while his Austrian friend said everything ran like clockwork. I never forgot what the head of Club Mistral once told me: "The HIHO event is the dream of every windsurfer. "

To us, HIHO is a little like a marathon where you have a few world-class racers, a bunch of strong amateurs, then the rest who just want to finish. HIHOers come with different goals and expectations. I like the participants who say, “I want to go to all the parties and then finish every race.”

So where do we go from here? We’re considering adding Stand Up Paddleboards and maybe kiting. We don’t stray from our tried and true formula of combining a great trip through the islands with racing and parties. I think I’m most excited about my 10- and 11-year old sons Sam and Josh who might tackle a few legs this year.  

Itinerary

Sunday, June 28
Registration at the Moorings. Board the yachts. Late afternoon departure for Virgin Gorda. 

Monday, June 29
Racing in Virgin Gorda's Eustatia Sound. Dinner in the North Sound.

Tuesday, June 30
Anegada race: Overnight on Anegada. Dinner and dancing at Anegada Reef Hotel.
 
Wednesday, July 1
Yacht race from Anegada to the Baths. Dinner at Last Resort.

Thursday, July 2
Race from Trellis Bay to Peter Island. Dinner at Pirates on Norman Island.

Friday, July 3
Race from Norman Island to Little Thatch. Dinner at Foxy's on Jost Van Dyke.

July 4
Final day of races at Sandy Spit or Sandy Cay. Yachts return to the Moorings for awards party. Dinner at Mariner Inn.

July 5
Disembark yachts by noon.