I also meant to ask if you knew about Active Captain for planning out trips? It is a great resource.
I also just saw your reply to FishSticks. You are right about the lack of good warm water beaches around here. But I still think that VA might be a little far for your experience level. But hey, you may be more risk tolerant then me (or rather my Wife because I would probably to that trip with your level of experience too).
“Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” -Mark Twain