Jimmy Buffett’s lifestyle is said to have epitomized “island escapism.” The musician took quickly to the habit of hanging around boats, especially sailboats. But sailing was more than just a muse for his music; it was his way of life.
Buffett was enamored by the sea. The grandson of a captain, he was a boat aficionado in every sense. His first boat was the Cheoy Lee 33 ketch Euphoria, which he traded for a 26-foot Alerion sloop designed by
Nathaniel Herreshoff named Savannah Jane in 1979. But when Buffett got aboard Ticonderoga (shown above) L. Francis Herreshoff’s famous 72-foot clipper-bowed ketch, he fell in love.
In 1980, journalist Craig Davis was brought aboard Ticonderoga for the annual Fort Lauderdale to Key West race. Buffett had also been offered a spot on the crew. Early in the race, a shackle on the mast snapped and the jib came down. Buffett sprang into action, hauling in the fallen sail on the foredeck. Another crew member, Joey Tress, climbed up the shrouds of the 85-foot main mast to retrieve the halyard. In a joking manner, someone on board retrieved helmets from below deck, claiming “we may need these.” Ultimately, the team finished seventh in their class but managed to set the record for the third-fastest elapsed time in the race.
Afterwards, the crew had drinks at the Chart Room in Key West, where Buffett almost bought Ticonderoga from her then owner Ken MacKenzie for what was reported to be “an amazingly low price.” Between drinks and hopping on stage to sing with the house band, Buffett mused about owning a boat like that one. “If I ever thought about getting another big boat, both for the way she sails and the history behind her, Ticonderoga is the boat I’d like to someday own.”
Following the race, Buffett would go on to buy many more sail and powerboats, including a Hinckley DS42 named Chill, a Tofinou 9.5 named Groovy, a Surfari 48 called Drifter, a custom 42-foot Freeman Boatworks design named Last Mango and more.
