The are plenty of anchorages in the Northern Chesapeake.
There is a great free dock In Chesapeake City on the C&D canal (electric and water a few bucks if you need them)..and the town is nice to walk.....also can anchor there...there are 2 marinas and Summit North a bit further east on the canal.
The Delaware has few anchorages so it's good to time tide and weather when going down to Cape May. It a HUGELY easy navigation exercise...just stay to the north/northeast of the shipping channel...plenty of water but some crab buoys. No traffic there other than a few fishing boats and rec boats.
The ferries are easy to navigate around once you get to the Cape May canal...stay close to their sterns when passing the terminal as it's very shallow a few hundred feet off their sterns.
The anchorage in front of the USCG base can be annoying and dangerous...there's a good one about 3 miles up the ICW called Sunset lake behind Wildwood.
The Jersey ICW is bad in some areas for depth...but certainly passable with a 37 footer (just did it in Dec in my 40)...just travel the last 3 hours of the rising tide and stop by the 3rd hour of the falling (plus have assistance towing...
). The next good inlet above Cape May is 15 miles North at Townsends Inlet, Great Egg is OK in good weather and Atlantic City is real good.
There's no appreciable current along the coast except right near the inlet mouths. Running south to north...running arounfd a mile off the beach is fine...particularly if you need to because of a strong northwesterly wind....most sand bars are on the north side of the inlets and the south side juts out...just be careful and jog to the sea buoy if in doubt.
I'd give you the rest of the Jersey ICW but after Hurricane Sandy...not sure how much has changes and how good the nav aids are....I"d probably skip it unless you get a goods report on it.
There are good anchorages along the Jersey ICW and there are nice little towns to walk/visit...though off season...weekdays would be slow and a lot of places may not be open yet (local assistance towing captains can give good recommendations for shoaling, marinas, restaurants, etc)
The marina in Atlantic City that Trump used to manage for the state is now managed by another Casino that bought Trump's casino and supposedly it's expensive but a great stop as marina transients get to use a lot of the casinos facilities.
When you get closer to leaving and firmed up a few ideas....shoot me a private message and I can address specifics a bit better.