FishSticks, thank you very much for the input. I'm sure we'll do plenty of puttering around New England (and maybe Long Island) this summer. The trip we're planning is supposed to be more of a getaway to someplace further, like a road trip, except by sea
New England also has a sad lack of beaches with warm water, even at the height of summer. The original plan was to head to Bermuda, but I quickly became convinced that we lacked the necessary experience, and also lacked the funds to properly outfit the boat for such a voyage. Virginia Beach was chosen because it has a reputation as a fun place and it has "beach" in the name. We're open to other possibilities, as long as they have beaches with warm water and a social scene with people of our age group. I don't want to make it sound like we're a bunch of alcoholics (we're not), nor is this trip meant to be a bender, I was just trying to communicate that we want a destination tailored to people of our age group.
What do you mean by there are no marinas with easy entry? That implies there are some marinas suitable for my boat? I've heard tales of how terrible the NJ coast is, and NC, but I can't recall ever hearing anything bad about VA. Virginia Beach appears to be right at the entrance to the Chesapeake, which everyone says is the sailing capital of the country! Thus I am confused about what makes this area unsuitable.