I stayed at marina's but...
you can probably find a place to anchor in Hemstead Harbor behind the breakwater that JP Morgan built (near town of Glen Cove). Time your departure to get the best currents through Hells Gate and NYC (it goes by quick with a 4-5 knot current) and find an anchorage behind Sandy Hook. Then a long trip to Atlantic City and then on to Cape May. You can make the C&D canal if you push but you can anchor in the Cohansey River if you want to take it easy. There is a breakwater next to the Nuclear Power Plant on the north shore further up that was used in its construction (some old barges were sunk to make it). I used it in a storm once in 1984 but they may have it off limits these days. There is a spot to anchor in the C&D canal but the Bohemia River has some better spots and is not much further. Rock Hall is your next stop. Say about 6 days underway if you push. Add time for an easier pace, wx delays and to enjoy the sights and adventure.I'd check in some cruising guides since it has been years since I made that trip. One, "Cruising the Chesapeake: A Gunkholer's Guide" by Willliam H. Shellenberger, is a good resource and has info about coming from NYC through Delaware Bay. Just what you need.