Jim McAlpine is the oldest participant in Oak Harbor Yacht Club’s weekly sailing races. Going on 88, his passion for sailing has led him on a lifetime of adventures. Photo by Daniel Warn/Whidbey News-Times

Yacht club’s oldest racer unfurls his sails for more competitions

As Jim McAlpine strolls the docks at the Oak Harbor Marina, sailors and deckhands greet him by name.

“When you get to be as old as me, you get to meet a lot of good people,” McAlpine said.

He’s going on 88, and still sails competitively, winning frequently. His “stack of trophies,” proves it, with a new win added as recently as April 13.

McAlpine joked that whenever he and his crew win a sailing race out of Oak Harbor Marina his competitors can’t help but consider his age.

“They get a little excited and say, ‘Hey, you’re supposed to be old and slow,’” he said.

But for McAlpine, sailing isn’t a passion that age can slow down. He routinely races every Thursday out of the Oak Harbor Marina as a member of the Oak Harbor Yacht Club.

He said that it doesn’t matter how old or how young a person is, all it takes is an interest in sailing and a body willing to participate.

“There are all these sails that never leave the marina,” McAlpine said, with a sweep of his arms over the marina’s crops of colored canvas.

“If you want to learn to sail your boat, go racing, cause you’ll learn,” he said. “If you have any competitive spirit at all, you’ll soon learn.”

McAlpine tends to say that each year will be his last racing out of the marina, but anyone who knows him laughs the notion off, thinking — correctly so far — that he’ll never give quit.

That’s because McAlpine’s white whale just happens to be Whidbey Island Race Week.

“We do Race Week every year,” he said. “One year we did very well; we were placed well up in the standings, but we never have really won it.”

Come July 10-14, when this year’s Race Week is scheduled, McAlpine will see if he can spear that prize.

“The nice thing about sailing is you never know it all,” he said. “There’s always something new to learn and that alone keeps you on your toes and keeps your brain working.”

McAlpine’s first brush with sailing came from joining the Sea Scouts in Michigan City, Ind., where he was born and raised. The interest expanded when his fishing spot grew too crowded, necessitating a pivot in hobbies toward sailing.

Next thing he knew, he’d joined a yacht club in California and had purchased a boat, which he and his family enjoyed through the 50s and 60s. He sailed the 14-foot boat for several years, before upgrading to a 22-foot cruising boat.

But McAlpine explained that he was always dreaming of a bigger boat, and eventually commissioned a 27-foot boat while he served in Vietnam.

Ironically, McAlpine fostered his love of sailing throughout a career in the U.S. Air Force. At age 43, he retired and set out on a series of seafaring adventures.

For starters, he and his wife sailed down the West Coast and looped on through the Panama Canal, which he said pushed that 27-foot vessel to its limits.

“Chancing the Panama Canal was really exciting,” he said. “Remember you have four line-handlers… One of my crew people, who were supposed to be monitoring, maintaining the strain on this line, let it go.

“We were spinning around in circles — inside the locks — and water was gushing in and there was a big ship behind me and another one in front of me. Fortunately, we got a strain on the line again and recovered a bit so we could get out of there.”

After the tumultuous canal crossing, McAlpine and company sailed through the Columbia and Venezuela region.

“The only thing you’ve got to worry about there was smugglers,” he said. “One little cove we went into one night, we noticed the trucks were backing down to the water on the shores, offloading.”

“We have no idea what, but obviously it was illegal.”

McAlpine’s voyages took him across the Caribbean — a seven-day, grueling trip. And from 1982-1985, he rented out an industrial space and built a 34-foot cutter, which ultimately took him to Whidbey Island in 1985.

He’s been here ever since.

On Whidbey, McAlpine developed his passion for performance sailing. As a result, he bought and rebuilt his current boat, an international One-Design J24 called “Lucky Jim.”

And McAlpine has been lucky. At least, he’s grateful to have let sailing be his mentor, to teach him about self-reliance.

“It seemed like every time we’d make an ocean crossing, we’d come back with a list that long about things that we had to fix,” he said. “The same is true in your day-to-day living — there is always something that didn’t go the way you hoped it would.

“You have to be prepared to work on yourself.”

Jim McAlpine, prepares his boat, called “Lucky Jim,” for a sailing race out of Oak Harbor Marina last week, a competitive outing for which he and his crew took home the top prize. Photo by Daniel Warn/Whidbey News-Times

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