To some degree the answer depends on what boat you take. Is that it in your photo
? If so it appears to be a good sized power boat
? If so the draft
might be an issue. If a large sailboat the mast
height could dictate the route
Also depends on weather
and if you are in a hurry or want to take your time and sight see the whole way.
Also the ICW
stops in Norfolk VA so from there you will be more exposed to open water
. You can stay inside to DE by going up Cheseapeake Bay to the canal, crossing to DE Bay and back south but from there you will have to go outside. If your boat is small enough you might be able to go back into the NJ Canal but you will have to go outside from north NJ to NY Harbor.
From there you have the option of going up Long Island Sound
or on the south side of Long Island
in open water
. Inside more protected and scenic, outside shorter and faster but exposed. Also inside you will be dealing with some fairly strong currents in spots as the tide ebbs and flows into LI Sound.