san padre to chicago
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for me it would be crazy,but im getting old,it does sound like a lot of fun.
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What about up the gulf of mexico to the mississippi to the illinois to the desplaines to lake michigan,I want to do that trip someday,I think you would be much safer that way,and you wouldn't have to worry about the weather so much.If I was gona take the east coast i would want to be in atleast a 50-60 ft yacht..
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I roughly calculated 6000 miles as well...which sound like a lot...until you break it down....if you average say 35 mph....thats only 171 hours.... divide that by say 12 weeks...thats less than 15 hours/ week....
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If the original poster is considering doing this in a 25ft boat, I'd recommend NOT doing it. There are times on Lake michigan just to travel 10 miles in a 25ft boat is almost impossible.