Even the dogs seemed excited as they trotted among the 150-some people milling around on Key West’s South Beach just after sunrise Saturday, May 16. And it’s no wonder, because they were about to witness a truly historic event: the start of the first U.S. government-sanctioned sailing race between Key West and Havana for more than 50 years.
The Havana Challenge featured five teams of American sailboat racers, most consisting of Florida Keys-based sailors, racing 16-foot Hobie Cat catamarans more than 90 miles across the Florida Straits to Cuba.
“Key West is unique in its location to Havana. We’re closer to Havana than Miami, and living and growing up in Key West, you just look that direction,” said race organizer and participating sailor George Bellenger. “It was a challenge that I couldn’t resist — so put the sails up and sail down to Havana.”
As the sun rose, heralding a blue-sky morning, the racers were intent on preparations: raising white and multicolored sails on their beached Hobie Cats, donning wetsuits and life vests, and stowing minimal gear. But they weren’t too busy to exchange greetings and hugs with well-wishers, pose for cell-phone photos and pat dogs including an engaging beagle named Marley.
Just after 7:30 a.m., the racers’ focus changed. After a brief team meeting on the beach, they pushed their Hobie Cats into chest-deep water and jumped aboard. Onlookers cheered and applauded, someone blew a few piercing blasts on a conch shell, and at 7:41 a.m. the race to Havana officially began.
Despite its lighthearted island-style start, this was not a casually-conceived affair. George and co-organizer Joe Weatherby worked closely with regulatory agencies including the U.S. Department of Commerce to get the necessary licenses for the teams to participate.
“The special part of our event today is that we have all the permits that make it legal for us to go, so we’re going to be setting a precedent today for others to follow,” George said before the race began. “We’ve gotten the Treasury Department permits, the Commerce Department permits, the Coast Guard permits — and permission from my mom.”
And the Hobie Cats didn’t sail alone. They were accompanied by support boats that brought the total fleet to 19 vessels.
“We’re taking down schooners to bring in the historical aspect, tying the knot with the traditional maritime heritage that’s been shared between Havana and Key West,” George explained.
The racing event also featured activities in Cuba, highlighted by a May 19 regatta between the U.S. sailors and elite Cuban racers off Havana. According to George, plans called for Cuban Olympians and members of the country’s national sailing team to participate.
The historic Havana Challenge is the latest manifestation of a cultural connection between Key West and Cuba that dates back more than 180 years.
In the early 1830s, Cuban people including scores of skilled cigar-makers began migrating to Key West, seeking personal freedom. By the mid- to late-1800s the island city was known as the cigar manufacturing capital of the world, and many Cuban traditions had become a vital part of its cultural mix.
In recent years, the waters between Key West and Havana have been seemingly irresistible to athletes and adventurers eager to test their limits. The most famous is endurance swimmer Diana Nyad, who successfully swam the distance in September 2013 after four previous attempts.
For George Bellenger, the Havana Challenge means far more than a pivotal ocean crossing. Just before leaving Key West May 16, he recalled a line from Ernest Hemingway’s “To Have and Have Not” that reads, “Brother, don’t let anybody tell you there isn’t plenty of water between Havana and Key West.” As he and his fellow racers made their final preparations to cross that water, George stated his purpose quite simply.
“We’re going out here today to show everyone that Key West and Havana are a lot closer than you might expect,” he said.
(Editor’s Note: Not all the Hobie Cats made it the entire way to Cuba, but all the sailors did. And by beginning the race, all five boats truly sailed into history.)