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Havana Challenge To Cross Straits Again, Under Power

Rob O'Neal
Havana Challenge

In May, five 16-foot Hobie Cat sailboats left Key West for the inaugural Havana Challenge sailing race to Cuba.

"Three of them were broken, one sank and one was ripped into pieces," said Joe Weatherby, one of the race organizers. The three "broken" boats were patched up enough to limp into Havana Harbor -- 10 hours after leaving Key West.

Weatherby and the other Havana Challenge organizers are planning a second race for November. But this one should go considerably more quickly because its entrants will be powerboats. Weatherby said he expects the fastest boats to make the 90-mile trip across the Florida Straits in an hour and a half.

The race is scheduled for a Tuesday, and the boaters would stay in Cuba until that Saturday. The race organizers have a series of events lined up, including a party at Morro Castle, a "Hemingway haunts" poker walk and a boat parade into Havana Harbor, "which just gives me goosebumps," Weatherby said. "We couldn't believe we are allowed to do this."

The Havana Challenge organizers are hoping to make the spring sailboat and fall powerboat races into annual events — with the possible addition of a tall ships challenge, Weatherby said.

"We see and now we know from our activities in getting the actual permits to do this that things are changing. And we'd like to be part of that change," Weatherby said. "It's really a cool place and a lot of fun."

Nancy Klingener was WLRN's Florida Keys reporter until July 2022.
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