Regatta organizers Joe Weatherby, left, and George Bellenger take a classic ride through Havana.

Robert O'Neal

“There are cultural and personal relationships between Key West and Havana that date back more than 100 years,” Weatherby added. “We are just trying to re-establish that relationship.”

The Bellengers and Weatherby worked closely with their counterpart in Cuba, Marina Hemingway Comm. Jose Escrich. Escrich arranged a flotilla in which the U.S. boats, proudly displaying flags of both countries, paraded along the historic Malecon highway. Such a flotilla of American boats has not taken place in Havana Harbor in more than 50 years.

The event proved that sports can sometimes transcend politics. The Bellengers, Weatherby and Escrich did what American and Cuban politicians have not been able to in more than 50 years: They brought the people of the two countries together.

“This is a historic day,” Escrich told his American counterparts at the welcome reception at Marina Hemingway. “Against strong tides you have made it here. Love has guided us here.”

The 90-mile crossing was a true adventure. Two catamarans capsized in the race over. One Hobie Cat was loaded onto a barge, repaired in Havana and sailed against the Cuban national team. The other sank 45 miles off Havana. Both crews were recovered unharmed by chase boats.

There were thrills of victory and agonies of defeat. The Hobie Cat regatta in Havana Harbor against the Cuban national teams proved disappointing for the Americans, as they lost all three races. 

The sign facing the United States Interest Section Building on the historic Malecon highway that read Venceremos!, “We Will Win!” foretold the out come of the races that pitted a ragtag team of Key Westers against Cuban national and regional teams, which will compete in the International Pan American games 

in Canada later this year. The first Copa De Amistad will stay in Cuba for now.

“We will be back,” Weatherby said.

Roughly 12 Key West boats, including the schooners Jolly Rover and Dream Catcher, ended the event with a 20-mile trek from Marina Hemingway to Havana Harbor. Crowds of Cubans lined the seawall to wave and cheer the flotilla, which displayed both American and Cuban flags. 

“This is big,” said Key West Mayor Craig Cates, who traveled to Cuba as part of the regatta. “I’m excited that boat traffic between Key West and Cuba has started to happen again. I really look forward to this event next year.”--Timothy O’Hara