Richmond or Virginia Beach

I would keep away from the Virginia Beach area. I love visiting there and find it a very cool city with a fun beach scene. I have only done one long ride in the VA Beach area and frankly, I found it very congested and not safe at all. The area surrounding Richmond does offer much quieter roads and has a very active running/triathlon community. As a previous poster pointed out, you are an hour from Charlottesville and that means access to the Blue Ridge Parkway for some serious climbing. Richmond allows you access to the mountains and the ocean.