Gotta wait out the insurance pitfall anyway on VA/NC border.
At least the insurance company is going to slow you down. We had club members that just got back from a trip to Canada
and the locks and all that. The leg to Cape May you have to be patient for the weather
and then hitting the tide for the Delaware River and the C and D canal. The Chesapeake is only an issue with weather as you can get strong NW winds and you don't want to be in the big part of the bay with the heavy chop. Lots of places to explore and hole up in along the way. Get a Chesapeake Bay
Guide as they have about the best guide made for any place. Covers all the anchorages
and what is on shore in exceptional detail and cute 3D sketches of how to navigate the anchorages
. We have decent weather until mid November when it can be spotty. Just be sure to make the weather work for you and don't try to fight with it. It's a lot of miles and you can't possibly have that much fight in you.
In the fall all these small towns are vacant and you get them all to yourself. The odd festival or two adds even more excitement. You just need to be looking in those off the beaten track places. Lots of really nice folks that talk funny