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[QUOTE="Baltic, post: 3972555, member: 965"]
I have been a sailboat owner and sailed all through New England and helped deliver boats up and down the East Coast. Sold the boat a number of years ago and chartered in different places, Caribbean, Pacific Northwest, etc. also was an ASA instructor in Mystic.
Chartering allowed varying experiences in different locales on boats I would otherwise never experience. There are Learn To Sail Chartering opportunities. 
I loved sailing but the bucket trip you envision would be best be done in a Trawler. You don’t go fast, but the Trawlers are sea worthy and much roomier than an equivalent sailboat would be. Also pretty fuel efficient. Even in a sailboat you would be surprised as to how often you would travel under power. I know a number of people who have done the circle up the coast, through the Erie Canal, Great Lakes and down the Mississippi. 
the other advantage of the Trawler on this circle is that you don’t have to dismantle your mast in those areas where there is a height restriction.
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