rmeader, I live here in Va Beach and what fishsticks was referring to about marina access for your boat is accurate. There are two entry's into VA Beach's marinas and both have bridges to low for sailboat accessibility.
That being sail there are plenty of marinas in Norfolk which is just right inside the Chesapeake Bay on the Norfolk side. This is where I kept my boat and they are many choices and price ranges. The trip to the ocean front from there is about a $35.00 cab ride. And yea there is plenty to do in Va Beach for your age group.
But, before making that kind of trip I would suggest if nothing else renting the life raft and getting an epirb. There is a lot of ocean out there and hugging the coast that time of year with the southerly winds will be almost impossible.
A people that values its privileges above it's principles will soon lose both.