Re: Chicago to South Manitou Island
Picking up on the black fly comments.... some "colour commentary". While this happened between Killarney and Bustard Islands on Georgian Bay, it applies here, equally.
Beautiful day, but not much wind, so I motorsail, in shorts, barefoot in boat shoes. Keep rubbing one leg/ankle over the other as the flies attack. When anchored at the Bustards I have to wash the cockpit floor where I stood while steering: it was entirely pink/red with (my) blood as I stood and crushed the flies that had been biting me.
As to your question about things that bother us when watching movies etc...
It is often too obvious when a scene is shot on a sailboat that is supposed to be under sail that, in quite a few cases, the director skips the sailing bit... The boat is virtually stationary, sometimes even with gently flapping sails, when the true professional would have the boat properly underway.
Anyway, since you say you know little about sailing, I would recommend that your editor (1) be familiar with sailing language/jargon etc... or (2) you submit your manuscript to a sailor with some writing skill to "vet" the accuracy of your language and the plausibility of your scenario(s).
Again, best of luck.