06/23/2026
Jimmy Buffett trivia time:
1. What Key West event began with three shots of tequila, a swim across a hotel pool, and a catamaran race?
2. What local entrepreneur rented the boats for the event—and built a side business rescuing customers when those same boats broke down offshore?
3. What happened to Jimmy Buffett’s boat during the race?
4. What mysterious vessel rescued the competitors after they found themselves drifting toward the Gulf Stream?
5. And what do all of those stories have to do with the title of one of Buffett’s most beloved songs?
The answer is “Nautical Wheelers.”
The story starts in December 1971, when Buffett, Tom Corcoran, and Phil Clark organized the Tequila Regatta at the Chart Room Bar. Contestants took a shot at the bar, swam across the Pier House pool for another, sprinted down the beach for a third, then boarded catamarans to race around the channel markers.
The boats came from “Swindle Wendell,” a local character whose rentals had a reputation for falling apart at the worst possible moment.
Sure enough, Clark tore a sail on the first marker. Buffett lost his rudder. Corcoran’s mainsheet failed. Before long, every boat was disabled and the crews had tied the catamarans together into one floating raft.
Instead of racing back to shore, they began drifting farther out to sea.
Their rescue came from a sleek black motor yacht that nobody recognized. No one ever appeared on deck. No introductions were made. A tow line came off the stern, the stranded sailors grabbed on, and the yacht pulled them safely home before disappearing from the story.
The other half of the answer was much calmer. Nautical Wheelers was also the name of a square dance club that met at Old City Hall, where locals gathered after work to dance under a parachute canopy in the afternoon shade.
One part tequila-fueled disaster. One part old Florida small-town tradition.