With the five foot draft you can take either the Virginia Cut to the Great Bridge Lock or the Dismal Swamp Route by the way of Elizabeth City to reach the
Chesapeake Bay. I personally like the Dismal Swamp route, but if it's June or July the biting flys in the Dismal Swamp are not an option! I would choose Cape May, Absecon Inlet, Manasquan Inlet and Sandy Hook (to Atlantic Highlands) as good potential stops on the
New Jersey Coast. Cape May offers a good anchorage just off the Coast Guard Station. Absecon Inlet (Atlantic City) has a great anchorage on the north side of the inlet
passage just before the fixed bridge at
Rum Point. Enter slow between the grassy bank to port and the sloping sand beach to starboard. Once your're in it's a great protected place. Manasquan Inlet is a simple straight shot, but there's no good anchorage and it requires a marina stay if you choose to enter,- call a marina ahead for space. Rounding Sandy Hook gives you an access down to Atlantic Highlands where you can find a protected anchorage just inside the breakwater. North
wind can be a bit disturing , but I do not see any east
wind problem here! Put yourself at the
battery (south end of Manhatten Island) to run with the
current up past Hell Gate and into
Long Island Sound. I like to stay on the eastside at Verrazano Bridge and take Buttermilk Channel east of Governors Isand to reach the East River. Also, look at the anchorage by Liberty Island just south and west of the Statue of Liberty. This gives you a shorter distance to time the current up the East River. North of Hell's Gate, it's a good choice to go between the two Brother's Islands. Have a great trip!