Re: milwaukee to gulf of mex
We did the trip in the fall of 2009. With weather delays and a detour a fair way up the Tennessee River to visit family, it took us about six weeks from Holland, MI to Mobile, AL. It wasn't the most exciting part of the Loop, but wasn't the worst either -- mostly it was just long days motoring towards warmer climes.
There's plenty of data on the web -- as MSN suggests, do a search with "great loop" in your definition.
FWIW, I posted random travelogue kind of updates over on AnythingSailing when we were doing the trip -- they may still be there.
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'85 BYB Vagabond 39