A lighthearted water-skiing jaunt doesn’t usually involve Cuban gunboats and 6-foot seas. But the late Key West mayor Charles “Sonny” McCoy encountered both in 1978, when he accepted a challenge to water ski from his island home to Cuba on a single slalom ski — a grueling feat that spanned 122 miles and took just over six hours.
A Key West native, McCoy was the son of a circus tightrope walker who once traversed part of the Grand Canyon on a tightrope. As a little boy he played with Ernest Hemingway’s sons, Gregory and Patrick, unaware that the man who yelled at him for making too much noise was the renowned writer.
Sonny was Key West’s mayor from 1971 to 1981. So his ski trip to Cuba, occurring during his tenure, seemed so bizarre that it earned national publicity. Most Key Westers, however, took it in stride — a testament to the island city’s prevailing quirkiness.
“In Key West, we’re a little weird,” Sonny admitted in an interview years later. “All we need is a stupid reason, or no reason at all, to do something.”
The mayor was already well known for skiing past Key West’s Mallory Square at Christmastime, dressed as Santa Claus and tossing gifts to kids on the pier. He also completed a nonstop 70-mile journey from Key West to the Dry Tortugas.
According to Sonny, the Cuba marathon wasn’t his idea. It was inspired by Wendy Tucker, then a young reporter for a Key West newspaper, whose non-local publisher didn’t believe her tales of the mayor’s water-skiing exploits.
To prove she wasn’t exaggerating, Wendy talked Sonny into the trek to the Tortugas. After that, his cronies figured a nonstop Cuba crossing was the next logical step.
Planning and carrying out the adventure involved then-President Jimmy Carter, numerous bemused officials and the Cuban government. A chance conversation at a national mayoral conference set plans in motion.
“A group of us mayors were having catfish and hush puppies with President Carter,” Sonny said years later, as matter-of-factly as though sharing southern-fried food with the president was perfectly normal. “At that time, he was kind of favorable to renewing relations with Cuba, and I told him what we had in mind.”
Whether because of the catfish or the concept’s breathtaking lunacy, Sonny and his slalom ski eventually got the green light.
A first attempt failed 20 miles off Havana after the ski skewered a floating bale of marijuana (known in the Keys as a “square grouper”) and McCoy’s hands, clenched around the tow rope’s handle, started bleeding too badly for him to continue.
The second try, however, was an unqualified success. With oven mitts to protect his hands, Sonny skied nonstop from Key West Harbor to Havana Harbor behind a 58-foot Hatteras called the Bullwinkle.
About 20 miles from Havana, Sonny and the Bullwinkle were greeted by a pair of Russian-built Cuban gunboats that provided escort. And after he landed in Havana, the Cuban government threw a party honoring his accomplishment.
“One minister at the party told me I had skied over an area where they caught the two largest great white sharks ever caught in the Atlantic Ocean, and asked if that scared me,” recalled Sonny. “I said, ‘Well, it would have if you hadn’t already pulled those two big mothers out of there.’”
Quickly becoming the stuff of legend, the feat even attracted the attention of famed newsman Charles Kuralt, who filmed a segment on Sonny for his Sunday morning TV program.
Sonny McCoy died in 2020, after being embroiled in controversy in his later years, when he had become a county commissioner. But old-time residents still remember his aquatic escapade — and Key West’s unique water-skiing mayor.
