I have a Cape Dory 28 and if all goes according to the revised plan, I will be doing the trip next year. Late summer or fall.
I am going to take the Erie Canal Hudson River way. In part because I've always wanted to and also because I have a brother in Boston. If I leave early enough, I will swing up around Long Island and the Cape to see the Bro and his family before going south. If too late, a potential routine would be Winter in the Carribean, summer in New England along with 1,000,000 other happy boaters.
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I will keep you posted.
TrT