One race. 240 miles. Our third try.

Day One (noon): We start the Port Huron to Mackinac Island sailboat race, one of the nation’s longest (200-plus miles up Lake Huron), largest (200 boats), oldest (97 years), and most prestigious regattas.

We’ve already motored our 38-foot sailboat, owned by friend Mike, out of the St. Clair River as part of the Port Huron Boat Parade. We waved at the hundreds of spectators lining the American and Canadian shorelines. Got misty-eyed as the bagpipers played for us.

Now we’ve started. We really hope to finish.

‘We’ includes our eight-person crew: My older brother Dave and three of his kids (Kameron, 31, Konnor, 28, and Khloe, 22), Dave’s girlfriend Colette and two of our friends, Charlie and boat-owner Mike.

Our last two attempts, in 2018 and 2019, ended in failure: One, due to a relentless series of storms. The other, due to a mechanical failure.

Day One (15 minutes into the race): We have a mechanical failure.

As we try to raise our spinnaker, there’s a problem with a halyard, one of the lines that go through the mast and pull the sails up and down.

Someone needs to be winched to the top of the 60-foot mast, under sail, while racing.

“I’ll go,” I say.

I pause to wait for someone to jump in and say, “No, Steve! While that is a brave and heroic offer, you’re far too old to do something this dangerous!”

Instead, my brother says, “We’ll get the bosun’s chair for you!”

A bosun’s chair is a specially designed device, with various safety hooks and straps.

The chair is in its original packaging. It still has the tags on.

I’m not usually an instructions guy. In this case, I ask for them.

“I can’t find any instructions,” Dave says. “But, there IS a promotional brochure.”

The brochure is a single sheet of glossy paper. On it is a photo of a guy sitting in the chair. The guy is clearly a model. He’s wearing a pressed Polo shirt and an ascot. I'm sure the brochure photographer, who is also probably not a seasoned sailor well-versed in the intricacies of this particular model of bosun's chair, simply told the actor to get in the thing however he saw fit.

We laugh but, disconcertingly, rely on the actor photo to figure out the safety chair.

Dave defines and clarifies everyone’s jobs. Konnor and Charlie will winch me up on one halyard. Kam and Mike on the safety halyard. Colette at the helm. Khloe relaying messages and watching for lightning or storms. Dave overseeing all of it.

There is not, I realize, another group of people I would want to have my life in their hands. Literally.

As soon as I’m hoisted to the top of the mast, a race helicopter starts circling our boat. I look straight into the eyes of the photographer taking pictures of me. A photographer in a helicopter. In the air.

I have to cut one halyard from the top of the mast, untangle another.

I’m up there, they tell me later, for maybe 30 minutes. I would have guessed longer.

We’re back racing again!

The forecast, though, calls for a relentless series of storms.

Will they finish? Will they finally, finally finish? Check out next week's Oddchester to find out.

Steve Lange is the editor of Rochester Magazine. His column appears every Tuesday.

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