Not much to add, but my wife and I just did the trip in our old Catalina 30.
We worked our way down from Massachusetts - anchored in Sandy Hook Bay for the night on Oct. 9th. Headed out the following morning on an overnight run to Cape May, spent a few days in Cape May (can strongly recommend Utsch's Marina)then headed through the cape may canal (don't forget, fixed bridge) and up Delaware Bay. We anchored for the night behind Reedy Island to wait for a good tide the following morning to get us through the C&D... we made Reedy Island to Annapolis, but it was a looong day! One more overnite should get you down the Chesapeake to Portsmouth...
Enjoy the trip,
Carlos & Maria
If you'd like to read a bit more about our trip or see some pictures, you can follow this link