Join Date: Nov 2009
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It's doable, but ambitious, assuming you are taking the outside route between NC and the northeast.
Note that it is a windward slog on your way home from Maine. On your return, you may want to start out early in the day and motor in calmer waters until the winds come up.
To give yourself a little more breathing room, you might skip NYC and save several days by taking a right turn at Cape May, NJ, and doing an overnight to Block Island on your way up (if the weather cooperates). If you haven't been in these waters, you might enjoy Block Island and then go on to Cuttyhunk. Provincetown could be your next stop after transiting the Cape Cod Canal. Then you might stop at the Isles of Shoals. Your next port would be in Maine, proper. Plan on 10 days to get this far if you are slowing down to smell the roses. Allow more sailing time to retrace this stage on the way home.
If the weather gods are with you, you could have a month in Maine to poke around.
BTW, have considered that the water is much colder than in NC, particularly north of Cape Cod? If you end up in the water, hypothermia is a concern. Also, you'll want to consult tide/current tables to plan a lot of your itinerary.