I sailed/motored a 26 footer with an
outboard many years ago from Gravesend Bay in
Brooklyn (not far from Sandy Hook), leaving in the AM on a rising tide in
New York. By the end of the day we were on a
mooring at Larchmont YC, having arrived at Hell's Gate at exactly the right time to ride the ebb into LIS.
It was very easy and fast, once we found the right day for the tides we wanted. These days, with
GPS, it has to be even easier to time your arrival at Hell's Gate. And yes, you do have to watch for debris (and
commercial traffic) in the East River and in Hell's Gate, so it's not something you want to try at night or in reduced visibility.
We departed from
Brooklyn so we could spend some time at my parents' house in Bensonhurst. And we were guests at LYC, so we could have gone further up the Sound if we wanted to. I'm sure we could have made it from Sandy Hook as well, just departing a little earlier.