Crossing the northeast corner of the Gulf of Mexico is the only part of the Great Loop where Loopers are forced out of sight of land. That's true even if you go around the Florida Bend like L.T. and I did because the Gulf is so shallow there that boaters unfamiliar with the area still have to travel 20-30 miles off shore. We were also out of sight of land crossing the mouth of the Potomac on the Chesapeake Bay - but that's because L.T. is not very tall, good for getting under low brides but not for an extended view.
No recreation boater has to be out of site of land on Lake Michigan, but it's still intimidating because it's BIG and has a reputation for blowing up in a hurry. Inlets to harbors and rivers are naturally spaced 10-30 miles apart along either side of the Lake. At any one time you could be 5-15 miles from safe harbor. Lake Michigan has a significant pucker power rating.
It also has annoying secondary wave patterns. All boats handle waves best on the bow. Waves from the stern require more attention but are generally OK as well – both, of course, depending on your speed and the size of the waves. Waves on your beam are always a pain in the butt, sometimes forcing a zigzag course to keep them on your bow/stern. Add secondary waves on the beam while already handling bigger waves on the bow or stern and the most patient Captain starts to grumble. L.T. wasn't happy either.
I’ve wasted a lot of time trying to figure out what causes secondary waves. I say wasted only because I’m back to where I started: Lake Michigan is big and has lots of room for multiple weather phenomenon that generate waves which can, and obviously do travel long distances, usually contrary to the dominant waves. Not to be confused with seiches which are more like tsunamis, dangerous to shores but generally not to boaters in open water.
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Big Sable Point Light
Grand Haven Musical Fountain
Grand Haven Inlet
L.T. in Chicago