The father-son relationship at the center of the St. Pete-Havana regatta

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regatta St. Petersburg Cuba Havana

A U.S. team participates in the 2017 St. Petersburg-Habana Race. Photo supplied by Richard Winning.

In 1930, a group of St. Petersburg yachters looked at a map of the Caribbean and decided the distance between their harbor and Havana was perfect for a middle-distance race. That year, they began a regatta tradition that would last just under three decades.

“It’s not a long race but there can be some [turbulent] weather,” said St. Pete yachter Richard Winning. Politically speaking, that’s what Winning’s father discovered as the commodore of the 1959 regatta, officiating the event just after the triumph of Fidel Castro’s revolution — and just prior to a five-decade freeze in U.S.-Cuba relations.

In late February, Winning finally had the opportunity to pick up where his father left off, coordinating and then serving as commodore of a 2017 St. Pete-Habana Regatta. “It was a fabulous feeling to bring it back again,” said Winning. “We just want to go down and sail and be in fellowship with the two nations.”

Sporting events such as this fall under the 12 approved categories of U.S. travel to Cuba, which existed before the Obama administration began easing restrictions for people-to-people engagement. However, the détente unleashed a rise in the number of Americans planning trips there, and Winning wanted to ride that wave.

This year’s regatta consisted of 80 boats carrying 700 sailors. Among them were two boats of wounded warriors, a blind sailor, and a crew of Cubans who received bilateral approval to sail up to St. Pete and race home.

In the old days, the regatta sailed straight into Havana Harbor, but this year participants sailed to nearby Marina Hemingway. Winning says one of the highlights was meeting his Cuban counterpart, Commodore Jose Miguel Diaz Escrich, both of whom shared childhood memories of the crowds watching the race from their respective shores.

“Back in the day, it was a huge promotional piece for the area because people traveled frequently from here to Cuba for weekend trips,” said Winning. “The race still promotes St. Petersburg and gets our name out there.”

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