Re: Maine to Chesapeake Fall Passage
This trip is a very common trip for delivery crews (although many keep going past the Chesapeake) in the fall and is certainly doable although it can be pretty cold and rough. It is not a bad shot from Penobscot bay, past Monhegan and to the Cape Cod Canal. If things get rough, Gloucester is a good place to duck into. On a 33' boat, the trip to the canal should be 18-30 hours depending on conditions (it will be a lot longer if you are trying to push or sail into a strong headwind and sea). Once you get south of the canal, harbor hopping your way down is not too bad or you can again run straight through. I would highly recommend going inside long island. Once you get south of new york, there are not many harbor options until you enter the Chesapeake. As long as you have cruising guides for all of the areas covered and do your reading ahead of time, there is no reason why the trip can't be done.
The real question is whether you and your boat are up to the trip. Do you feel sufficiently experienced? Do you have anyone going with you, this would help a lot? Is your boat in good shape? These are things that only you can decide.