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He really should take sails along and learn to sail as he travels. There will be plenty of time. Plus, sails will make his boat much safer when he gets out of teh waterways into the Gulf.
He also should bring earplugs. A few months in close proximity to an outboard engine could be bad for his ears.
Does he plan to take the Eire canal from the Hudson River all the way to Lake Eire?
If he jumps out of the Eire Canal through the Oswego Canal into Lake Ontario, he will be stuck. The Welland Canal between Lake Eire and Lake Ontario will not allow transit of such a small craft (pleasure craft must be at least 20' in length and weigh over one ton).
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