Congrats - which boat did you buy?
I delivered my J/109 from Annapolis to Newport in Oct 2013 and went North up the Chesapeake, through the C&D Canal to Cape May, then went direct to Newport from there. See the attached route plan. I took 3.5 days, but on a J/30 would probably take longer.
I've also done a trip from Newport to Raritan, NJ that would allow you to do the inside route.
Check
this link for
CHNYC (Newport) to
Cedar Point YC (Westport, CT). Noank is on the way for this and allows you to cruise inside Long Island, through the East River, then down the Jersey shore.
If you did it with a Captain, would you crew also?