Re: Getting ahead of myself
How exciting! We made the reverse trip moving my C&C 24 from Long Island Sound to Bohemia Bay Yacht Harbor. Hauled out and spent the winter at Delaware City. It's a great little marina with a friendly staff.
Obviously, the weather generally and wind strength & direction specifically will be the greatest unknown. The Delaware Bay is shallow and notoriously choppy (Our trip from Cape May to Delaware City was the worst sail of my life.)
There aren't many stopping points in route, so once you are committed, be prepared to complete the trip.