I teach sailing on the Potomac
just below DC and race
regularly on the Chesapeake. I brought a Jeanneau43 down from Manhasset last May through the C&D and to Tolchester on the Eastern Shore opposite Baltimore
. I might be interested in joining you for the trip, most probably with a decent but less experienced sailing friend.
I've done variations of the trip you propose a couple of times and your plan seems sound with one possible exception. It's a long way up the Potomac to DC and then back down. It's do-able, but you'd cut off a lot of water
travel by staying on the Bay, going to Annapolis
and getting the 30 min drive into DC, which I could probably arrange if aboard.
I have a sister in Manhasset and will be there Easter Sunday and probably the Monday after if you'd like to meet.