Congrats on your new boat purchase! I keep my boat in Deltaville and would offer to go with you, but I don't have much interest in doing a delivery in December. Even a 30 mile day sail.
I mostly sail north of you on the Chesapeake, but I've anchored in Back river a couple times. It's a relatively easy trip from there to Portsmouth. But because of the short daylight hours, new boat and your inexperience, you should probably motor the whole way. I wouldn't want to be coming into Norfolk in the dark. Norfolk is perhaps the most crowded harbor on the East Coast. Manhattan may give it a run for its money, but I think Norfolk is worse because there is so little water to get out of the big ships' way.
You will almost certainly run into Coast Guard security and patrol boats entering Norfolk. Make sure you have all required safety gear with you so you don't get in trouble if you are boarded. Also useful in case you have an emergency
If there is a small craft warning or really crappy weather on the 29th, I'd probably postpone for a better day. Better to be safe than sorry in December.
To find someone to go with you, you might head down to the southern most boat basin in downtown Portsmouth. There was a coffee kiosk there where local sailors hung out in the morning. Last I heard, the kiosk burnt down, but I imagine it was rebuilt. You might find someone to go with you there, or at least get some advice on the trip. Although, with Ray's experience and requirements (hey, I'll need a ride back to my car), I'd definitely take him up on his offer. Good luck and have fun!
Gemini Catamaran Split Decision