You are firmly in “if you get
lost, just pull in some where’s and ask directions” territory! Not to sound pedantic. But you cannot pull into a marina in the Chesapeake and fail to find a great spot.
I’d load the
boat up for 4-5 days of self sustainability just to be safe should you really feel compelled to
anchor (bring a crab trap too!), but you can easily load up at any of the
marinas there.
So many great memories over there make me truly envious of you. Go out and have fun. Don’t over think it, it’s a very permissive cruising ground. (Of course never under think it too).
I also really recommend a stop at Tangier Island as well.
Have fun!!
And I just re-read your post about the marina avoidance.
Annapolis is very easy to
anchor in and runs. Dinghy to the municipal sea wall. I recommend Hampton,VA too!