My parents and then their 4 children had a home in Chilmark for almost 50 years.
Depending on draft and weather conditions, I would go:
Up the Chesapeake to the C & D canal.
Down Delaware bay to the ferry channel into Cape May.
Depending on your draft, I would plane on the ICW up to Manasquan Inlet. You could also go up the NJ coast if you get a good weather window.
Either way, you will need to go up the NJ coast to NYC.
You will probably want to go out Long Island sound.
From their, I can't help you as I haven't gone East of NYC by boat.
I'm tired of fast moves, I've got a slow groove, on my mind.....
I want to spend some time, Not come and go in a heated rush.....
by The Pointer Sisters