Good morning,
I did the same trip last fall on my
Lagoon 470. Other than along NJ you don't have to stay outside until the mouth of the Chesapeake.
Route we followed doing virtually all day hops was (I didn't look at my log so might have missed a stop or two.):
Depart
NYC
Sandy Hook
Atlantic City
Cape May
Half way up Delaware Bay (anchored in bay out of channel).
Through the Delaware-Chesapeake
canal (over 150' bridge clearance as I recall)
Anchored on Chesapeake end of
canal
Baltimore (anchored up at very end in front of old submarine)
Annapolis. (Lagoon throws a good party for all
Lagoon owners).
Lots of options between there and Hampton/Norfolk area.
Feel free to PM me if you want to get specifics.
Bill