Once in Ocean City, the isn't much water except for a little way after you hang a right after the entrance.

What do you sail mnh?

Going into Norfolk, Hampton, and environs is pretty confusing at night. Even with a chart plotter, there are a lot of lights and traffic. The naval vessels don't always use lights, unless something has changed. They will not likely talk with you.

The trip from Ocean City on south is an overnight. I wouldn't try any inlet south of there.