KCDW
Nice one - I did it twice last year (solo) in a rented Warrior out of CDW, once continuing down the NJ coast to Atlantic City, and once along the south side of Long Island and on to Block Island.
If you continue over the harbour at 1000' or thereabouths you need to get round or over the Verrazano bridge, which must have towers up to about 800'. If you take the central route it feels like you are flying right through the bridge supports!
If you carry on down Long Island you can transit about 5 miles south of JFK, offshore not above 500', and talk to Kennedy Tower on the way ('caution wake turbulence from aircraft departing above you').
BTW - I hope you observed the 1 mile exclusion zone around the Statue of Liberty, or has that been removed.
I'll post a photo if I get a chance.