If you are looking for night life, Urbanna has the most choices. I second the Carrotoman, especially the western branch. The eastern branch has a great anchorage with a nice beach but generally overrun by jetskis. All the other suggestions are great and visit them often, but tend to be away from towns. We're a pretty friendly lot, drop your anchor
over and say hello. Also consider joining one of the local Yacht Clubs, most are pretty laid back social organizations. Fishing Bay, Yankee Point and to some extent RRYC on Carters Creek are into racing.