The Highlander sailboat was conceived in Vermilion and created in Fairport Harbor. Sixty-seven years later, one of the country’s oldest and largest fleets of Highlanders calls Cleveland home.

About 20 of the 20-foot dinghies sit on trailers on the grassy gravel at Whiskey Island. The oldest here was built in the ‘60s, the newest this century, said fleet co-captain Gary Vinicky, of Elyria, as he gives a tour. But they’re all one design, with big mainsails, roomy hulls and no motors. They can compete evenly against each other.

“It’s challenging. It’s work, but the rewards are immeasurable,” said Vinicky, who wore a T-shirt with the Highlander logo of a dancing skirted Scotsman. “The self-satisfaction you get when you figure it out.”

They work to figure it out every Wednesday and Sunday night, when sailors roll the trailers to a hoist at the water’s edge, drop the boats into the marina, and race.

“There’s nothing like stepping on to the boat to erase your slate,” Vinicky said. “It’s a midweek break from all your tensions.”

The Highlander fleet has been here since 1994, when businessman Dan T. Moore owned Whiskey Island. But the fleet will celebrate its 60th anniversary next year. 

The Highlanders are different from bigger sailboats, which have weighted keels to help them stay upright in rough waters. The Highlanders are stored out of the water. And sailors have to rig the rudder and tiller each time they take out the boat.

Vinicky and his crew can be in the water in 20 minutes. But that’s after 40 years experience.

“A lot of the power boaters say it’s too much work. They just want to turn the key and go,” Vinicky said. “But it’s not about point A to point B. It’s about the journey.”

Each Highlander is numbered.

Aficionados know which was built by Douglass and McLeod, then by Customflex in Toledo and now by Allen Boat Co. in Buffalo.

When the boat debuted in the 1950s, after being designed in the now Chez Francois building in Vermilion. (The first of the Highlander’s precursor, Thistle No. 3, hangs from the Touche restaurant now.)

There were once Highlander fleets up and down the East Coast, throughout the South and Texas, and around the Great Lakes in the United States and Canada. Over the decades, as fiberglass replaced wood hulls and synthetic sails replaced cotton, boats and yacht clubs got fancier, and Highlanders grew rarer.

Mentor Yacht Club’s Fleet was the first, but it no longer exists. Now there are just 12 fleets listed by the Highlander Class International Association.

Cleveland’s Fleet 14 (since it was the 14th in the country) remains relevant by recruiting members at the Mid-America Boat Show each winter. Vinicky also credits Whiskey Island for the low-cost dry storage lot, which costs about $400 per spot each season.  

Highlanders aren’t fancy boats, and owners generally can’t afford yacht club membership fees, he said. He hopes the Cleveland Metroparks, which now own Whiskey Island, create another affordable dry storage area at East 55th Street Marina on the East Side.

“Everybody thinks you have to be rich to do this,” Vinicky said. “You can buy a boat for $1,000 and be competitive.”

It’s not about the money. It’s about the challenge, the teamwork, the friends you make.

“It’s work,” Vinicky said. “But the rewards are immeasurable.”