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Gap year afloat

Nov 1, 2018
Gap year offshore sailor Kai O’Connor.

Gap year offshore sailor Kai O’Connor.

Sue Hadlock

Most recent high school graduates head to college or the workplace. Kai O’Connor went to sea.

The 19-year-old from Corinth, Vt., spent his “gap year” sailing between Freeport, Maine, and points in the South Atlantic and Caribbean Sea aboard his restored 27-foot 1968 Pearson Renegade Scoooch. Tania Aebi, who sailed around the world more than 20 years ago, is his neighbor and was his inspiration for the voyage.

“Growing up, I wanted to sail around the world,” he said in a recent interview. “I decided to buy a boat but I didn’t really have a plan. I just knew I just want to go sailing.”

O’Connor had a good sailing background from his grandparents’ yacht club in Freeport, but the voyage was his first bluewater sailing experience. He navigated by paper charts, aided by apps on his smartphone.

He dealt with sporadic problems throughout the voyage, including recurring issues with the engine and autopilot. O’Connor called on his experience working on engines growing up to diagnose and address the problems while at sea.

“I had grown up working on cars so I knew engine stuff, which helped a lot when the engine broke many times,” he said.

O’Connor, now a freshman at the University of Vermont, worked during a two-month stint in Florida to help fund the voyage. From there, he traveled to the Bahamas, Jamaica, Cuba and Mexico over eight months. He returned in June 2018.

Along the way, he saw dolphins, pilot whales and myriad other sea creatures. At one point in the Atlantic, Scoooch rode over a pilot whale. “I didn’t realize it was there,” O’Connor said. “I kind of bumped over it. I am pretty sure it was alright.”

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