Re: Maine to Chesapeake Fall Passage
Atlantic highlands to Cape May is 105-110 nm in a straight line sail. Averaging 5 knots that's more than a long day. That's 20 hours. The time of year the OP is going with 11hours or less sunlight would make it a day and a night.
We haves used Reedy Island about 7 miles south of he C&D Canal as a stopover point in case you can not make it o the canal or yu want to Tate for the run down the Delaware River
The whole way with the tide.
I have done the trip to New England or back over 35 times. There re advantage to doings hot fro Block to Cape May as well as disadvantages. Crew strength and experience as well as boat preparation are definite factors.