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As an experienced Lake Michigan boater, I can tell you that is an ambitious one day round trip. I have wanted to do it for years in my Outrage 25 with twin 200's, and have never been able to catch the right weather window for several days in a row, even for a boat like that.

With your small boat fleet and single engines, be sure each boat carries enough fuel for 90 miles each way. Also be sure at least one boat has a decent towing harness, about 100' long, in case someone has engine trouble. A tow line has to be hooked to the bow eye and stern eyes, not cleats.

I am actually heading up there for five days in the Door County peninsula for some "Ribside 21" boating in about an hour, and will actually be stopping at the Manitowoc Marina, and also Twin Cities this afternoon, on the way up.

Have an enjoyable and safe trip! The nearby WWII submarine museum in Manitowoc is worth a visit. You can go on the sub. Over 60 were built there during the War. With the longer days, I would stay a little longer on the WI side.