St Augustine, FL to Savannah, GA. Then to Charleston, SC. Cedar Island Ferry to Okracoke Island. Stay overnight in Okracoke village, either camping, or at a B&B. Then catch the ferry to Hattaras Island and drive it all the way up. Work your way over to Virginia Beach, Norfolk, Newport News area then to Yorktown and Williamsburg. Hit Richmond, Fredericksburg and DC. Hang at Baltimore's inner harbor. Hit Ocean City if you like the beach. Check out Lancaster County, PA (Amish country). Go to Gettysburg, then Philadelphia. Stop in Hershey. On to New York, Boston and Montreal. Check the botanical gardens in Montreal. From there to Niagara falls. Go to Pittsburgh. Catch the Blue ridge Parkway and ride it to Asheville. Work your way down to Atlanta, then New Orleans. That's probably the route I'd take.

Oh, and like Bitt said, eat lots of barbecue in the south. It changes a bit everywhere you go. Find out where the "good ol' boys" eat barbecue or look for a crowded lot with lots of pickup trucks. Eat there.