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Re: Lake Michigan 19 foot and under
I used to race on Lake MI in a fleet that included a 19' Lightning, not too different from a Flying Scot. He even flew a spinnaker most nights.
In most of the channels that go into Lake MI on the MI side, getting out of the channel will be the most exciting part of your trip. In a West wind, getting out of the channel may even be dangerous in the ports without breakwalls. Other than that, just pick good wind and wave days for your vessel.