Re: Maine to Chesapeake Fall Passage
I did most of that route two years ago on my Catalina 27. Get the current Eldridge Tide & Pilot Book first. It will carry you all the way from Penobscot past NYC for tides and currents and more. It's extremely helpful on this trip. Also, take the Cape Cod Canal instead of going outside.
I alternated between anchoring out overnight and staying at a marina, but mostly due to limited tankage. Let me know if you need particular information, like marinas that were wonderful and those that were not so much.
1982 Catalina 27