Yes you can cross the Chesapeake Bay Bridge. We went that way to OBX but we live on LI so not sure how far you will go in first day. The eastern shore is accessed through route 13 or 113 and is a step back in time. On the Eastern Shore we have stayed at Toms Cove in Chincotegue VA, 8 hours from Eastern LI, and Cherrystone in Cheriton 9 hrs from Eastern LI. Cherrystone is 11 miles north of the Bay Bridge. (If you have kids, you may never leave there!)Then South over the bridge into Norfolk where we took 17 to OBX. We stayed at Camp Hatteras in Waves on the ocean side. the CG spans the road so bay side for sunsets, jet skiing, paddle board etc, ocean for beach. We stayed just a couple sites away from the beach entrance and could here the ocean every night. There is no view as the dunes are high. It was expensive then $85/nite plus a cable charge for tv, but we would go again. DM me fo rother suggestions if needed. Happy Trails. Im jealous...