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 speed
trawler: Krogen, Defever, etc. Search on Yachtworld using
trawler as the
boat type and your
price limits, size, age, etc.
David