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I've done it many times. Height will be the limiting factor because if you're over 21' (?? Can't remember exact limiting height) you can't go through the NY State barge canal. The trip through the St. Lawrence is pretty, but much longer! The trip from NYC to Troy (2st lock) should take 1-2 days. The canal system will then take another 2-3 days. After that, you've got the trip from Oswego to the Welland Canal before transitting Lakes Erie, St. Clair, Huron, and then Michigan.
The NY trip is also very nice.
Sailboats will have the mast stepped at each end.
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