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I guess depending on the boats and crews involved, I'd jump out of the Delaware, make one long passage to the eastern end of Long Island Sound. While it means a day or two at sea, it would allow you to pick your weather window and cut days out of the trip north which would allow a more reasonable schedule coming home. Otherwise, you are talking about two pretty tough deliveries back to back. It's not my idea of fun.
One more suggestion, would be to break this into two or three trips. Get you boat up to the Sound, Leave the boat up there, catch your breath, go home, do some work if you must, spend a week poking around the Sound. And then catch a norther and come back home when you can.
Respectfully,
Jeff
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