I did not construe anything you posted to mean "DEFINITELY DO NOT ATTEMPT THIS TRIP"
What you said is very good info. Although I haven't done any boating in the Chesapeake area we have lived in Maryland before and I know how the weather can be during the fall. Some gorgeous days full of sunshine and mild temps, some days with raging wind and quite cold temps, rain, and sleet.
I threw out there that I have time to spare for precisely the reason that I can 'hide out' when necessary for several weeks (in total, not at one time) if it came to that. I will point out that I am kind of a sissy when it comes to cold so I would prefer to hide from bad weather on a dock where I can plug in and run the heater