The only advice I would have is:
1. Get advice on the stream to get the best results! Jennifer Clark or Chris Parker can help among others.
2. Stay on the north/west edge of the stream so you can get out of it if bad weather/squalls are forecast
. GET WEATHER every 6 hours at a minimum.
3. Point for Beaufort
NC...not Hatteras. Do not commit to going around Hateras until you get there and have a clear forecast
. Hang in Beaufort
for a day or two if you need to wait for weather....or just go up the ICW
to Norfolk and out the Chessie Bridge Tunnel again if you need to keep moving.
From the Chessie...I would head
to Montauk directly rather than NYC
as it is easier sailing than along the coast. Took us 2.5 days in a 50 footer...easy with a decent forecast.