Advice for Cruise to Maine

[DennisM]

Sometime near the end of this month, I'm headed out for a cruise from Kingston, NY, (up the Hudson River about 90 miles north of NYC) to Castine, Maine. It will only be my second cruise. Last year, I sailed to Greenport and back with a friend, so I think I know that part of the route fairly well enough.

I would love some advice on any and all aspects of the rest of the trip, say from Newport to Maine and back. My plan at this point is to stop at Newport, Cuddyhunk and Provincetown. I will have one crew member, (the same friend, who is far more experienced than I), and if a third person meets us in Ptown as he says he will, we'll head overnight directly to Matinicus, provided the weather godz will allow. If they won't, we'll probably bump our way cautiously along the coast from Gloucester northward.

Any insights, cautions, do-not-miss info, etc. would be much appreciated.
Thanks in advance,
- D