Depends on your experience as Moody46 CC says.
If you buy in NJ and don't have to deal with the East River, it's pretty easy. From LIS, you'll have to transit (motor) down the East River which can be a bit tricky, but very interesting. Don't let it scare you, but do be meticulous about calculating the tides and currents. Hell Gate can be great fun if you're running with the current
(11+ knots SOG at the height of the current) and impossible if you are not. The same with Delaware Bay. You must calculate the tides right or you'll be standing still against the current at best. The offshore passage
in good weather
is otherwise unremarkable, except that Atlantic City can be seen from many many miles away at night.
is LIS to either City Island or Manhasset Bay to wait for the tide in the East River. Transit down the East River and anchor
in Sandy Hook (or NY/NJ marinas
if you want to visit the city). Sandy Hook to Cape May, and anchor in Cape May to time the tides for the Delaware. Nice lobster house in Cape May. Then motor
up the Delaware with the big boys and through the Canal. Nice stop is Schaefer's Canal House or the Bayard House. Then take the opportunity to cruise
down the Chesapeake, stopping in St. Michael's/Oxford, Annapolis
But if you live on the lower Chesapeake and want to experience a really nice offshore passage
, why not sail out from Montauk or Sandy Hook to Hampton Roads
, Virginia? No motoring that way. Depends on how far down you are and whether you get a weather window.