Hello Ken: Welcome to Tidewater if it happens. I'm up on the York River (second one up) so am not as familiar as I should be with the Marinas down around VB. Right next to the Chesapeake Bay Bridge Tunnel where the Naval Amphib Base is located is a cluster of marinas, that are protected somewhat. This is in the Pretty Lake area, really easy to get in and out of without tidal restrictions. I don't know of any that are south of the Bridge Tunnel other than a couple at Rudi Inlet, but the bridge restriction is a problem, and this dumps right into the ocean.
If you are going to be in VB the area next to the amphib base may be your best bet. There are a couple located at Willoby Spit, right next to the Hampton Roads Bridge Tunnel, and there is one located at Ft Monroe, as well as the marinas downtown Hampton. Further up the Hampton Harbour at Portsmouth is Tidewater Marina. Just above Ft Monroe is Buckroe and there is Salt Ponds Marina. All these are at the bottom of the bay so to speak. You will enjoy Mobjack Bay, with the East, North, Severn and Ware Rivers for nice weekend runs with pristine anchorages.
There are so many places to go on the Chesapeake, it may use up a good portion of your lifetime. Eastern Shore has lots of nice spots to visit as well as Tangier Island, Tangier Sound and points north. You will find that time will be your biggest constraint as it can get away from you quickly. We can go out and gobble up a week before we realize it is gone.
Look us up if you make the transition.
Tom