As the previous poster noted, there is no ICW until you get to Norfolk, Va.
In most cases you would go west through Long Island Sound
and under the Throgs Neck Bridge to NYC
, down the East River and then past lower Manhatten and under the Verazzano Narrows Bridge. Then hug the New Jersey
Coast down to Cape May and up the Delaware Bay to the C&D Canal to the Chesapeake. Then down the Chesapeake to the beginnings of the ICW at Norfolk.
You will need a reasonably seaworthy
boat, ie no house boats ;-), but most cruisers in the size range you are talking about can handle that voyage.
Look for a displacement
: Krogen, Defever, etc. Search on Yachtworld using trawler
as the boat type and your price
limits, size, age, etc.