Re: Chicago to South Manitou Island
Best and worst. Great question. I love losing sight of land. Nothing but blue all around and the sky above you. Similarly, at night, while the glow of Chicago and Milwaukee are often visible far off in the distance, the light pollution disappates and can see thousands of stars that were invisible to you when you left port. If you are on the big lake at night in late July and early August, you'll no doubt be treated to a light show from the Perseids meteor shower. That always enlivens a night watch.
I think someone else mentioned the biting flies. When the come, they come in large numbers. Your legs will be mauled and there will be dead flies all over the cockpit. That's not so good. I could also do without the short period, flat-faced waves. You and your boat can take a real beating in waves of heights that on the open ocean would be nothing more than gentle swells.