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.):
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
(anchored up at very end in front of old submarine)
. (Lagoon throws a good party for all Lagoon
Lots of options between there and Hampton/Norfolk area.
Feel free to PM me if you want to get specifics.