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I've never looked close, either way you'll need to get charts and pay close attention to depths and bridge clearances. That said...
I'm not sure you can get from Lake Michigan to the Mississippi in a keelboat, but if you can I'm sure someone will correct me. And even if you can get to the Illinios River and into the Mississippi I'd bet you'd have to do most of the trip to New Orleans with the mast unstepped, and you are going to do a lot of motoring.
I'm also not sure you can get out through the St Lawrence w/o unstepping the mast, but you might be able to, and if you go that way you should be able to sail except for parts of the St Lawrence Seaway portion, you'd be able to sail the Great Lakes.
Once you get to the Atlantic the choice to run outside or in the ditch is up to you. You can always run outside and duck in for weather and to anchor, assuming there is no rush.
The easiest way, and possibly the cheapest when you really get down to it, is to put it on a truck.
My question is why buy the boat there? In the shopping I've been doing boats in the great lakes cost at least 20% to 30% more than boats at the coast.
Again, I've never looked close so the inputs pretty useless but maybe some ideas to think about.
Last edited by XTR; 01-15-2010 at 11:55 AM.