FREEPORT — Kai O’Connor paid $1,000 in spring 2017 for a 27-foot 1968 Pearson Renegade sailboat with a rotten deck and algae in the cabin. He spent the summer after his high school graduation fixing it up, and finally put it in the water in Maine in October.

“It started to sink,” said O’Connor, now 19.

He repaired the leak. Then he set sail on a solo journey that would take him 5,200 nautical miles to the Bahamas and back. It was his first time sailing a boat longer than 14 feet, and the realization of an idea from childhood.

O’Connor returned to Freeport on Saturday just in time for orientation at the University of Vermont, which he plans to attend in the fall.

“There were moments when I was sailing, I realized I was completely alone on a sailboat, solely responsible for everything in my life, but I was still happy and safe,” O’Connor said. “I think I grew a lot, living on my own, and also living on my own on a boat.”

O’Connor was born in Maine but grew up in Corinth, Vermont. His mom, Kimberly Hotelling, is from Freeport. She took sailing lessons at the Harraseeket Yacht Club and loved being on the ocean in her family’s boat. Her son’s name means “ocean” in Hawaiian, she said.

She remembered when her son built his first boat out of foam insulation and wood from the garage. It had a bedsheet for a sail and could float on a neighborhood pond. He was 5 years old.

“He was always drawn to boats and the ocean,” Hotelling said.

The family visited his grandparents in Maine in the summers, and O’Connor took sailing lessons at the same yacht club. He loved racing 420 sailboats and started talking about owning his own boat when he grew up. When he was a junior in high school, he started shopping.

“I realized it was always going to be a far-off dream if I didn’t buy a boat,” O’Connor said.

He bought a couple of duds before finding Scoooch. It was in poor condition, but O’Connor could tell the rigging was still in good shape, and the shiny chrome winches caught his eye. He had experience working alongside his dad, who is a carpenter, and messing around with the engines in old cars.

“I said, ‘That’s a nice boat,’ ” he said.

Hotelling said her son had talked about a sailing trip for years, but seeing the boat made it real.

“I still thought it was a lovely idea, but it was a little different when it was a reality,” she said.

O’Connor found mentors – a friend of his grandparents who had sailed to the Bahamas many times, and Tania Aebi. Aebi was not much older than O’Connor when she became the first American woman to circumnavigate the world alone in a sailboat, and she happened to live in his small town in Vermont. The mentors gave him tips on safety and places to stop along his journey.

He left Oct. 10. That first night, the waves were choppy, the engine died, and O’Connor got seasick. But he eventually made it to Provincetown, Massachusetts, and then Southport, Connecticut.

Kai O’Connor at age 5 sails around a pond on a boat he built himself.

He repaired his engine, and continued down the East Coast until he ran out of money in Florida. For two months, he lived on his boat and found a job doing maintenance on yachts. Then he set sail for the Bahamas and landed there in January. He stayed there for two months, cruising the islands.

His parents visited him there in February to celebrate his 19th birthday. On their final sail together, the boat was heeled over from the wind and the waves were crashing in, but Hotelling said her son managed with ease.

“It was really neat to see him sail his boat with such confidence and competence and feel really safe,” his mom said.

O’Connor eventually continued his journey to Jamaica, Cuba and Mexico. He stocked the boat with rice and pasta, cans of vegetables and fruit. He used apps on his cellphone to help navigate and monitor weather conditions. When his engine and his autopilot failed at different points along the journey, he repaired them himself.

He said he didn’t mind being alone because it forced him to meet people along his journey. One of his favorite days on the trip, he said, was spent spearfishing with other young sailors he met on an island in the Bahamas.

O’Connor, 19, poses on his sailboat Sunday in South Freeport. “I think I grew a lot, living on my own, and also living on my own on a boat,” he said. Only once on his eight-month journey did he feel like stopping, he said.

He only had one moment when he wanted to give up, he said. He was sailing from Mexico to Florida with a broken autopilot, and the rough water brought on his second and final bout of seasickness. The waves were knocking the dinghy off the boat and he had to secure it in the bad weather.

“That was the only time I wanted to stop, but I couldn’t,” he said with a shrug.

O’Connor sailed back up the East Coast, returning to Freeport on Saturday. His family met him in Casco Bay on a friend’s boat.

“People say, ‘Aren’t you relieved?’ ” Hotelling said. “I wasn’t really nervous anymore. I just felt proud.”

O’Connor plans to spend the summer working with his dad in Vermont and sailing in Maine when he can. He will study engineering at the University of Vermont in the fall. But sitting Sunday on Scoooch, he was already planning his next trip. He wants to explore the northern latitudes more, he said, maybe sail around the world.

“I come up with a new idea every day,” he said.

Megan Doyle can be contacted at 791-6327 or at:

[email protected]

Twitter: megan_e_doyle

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