Well..... Annapolis and Chesapeake Bay is the sailing capital of the world. It is called for good reasons. Having said that, every year after July 4 to late Aug, all we can do is motoring around basking in the sun with 100% humidity. The bay water is heavily polluted, you can't even see your toes. I don't let my children touch the water.
Other than these two, I think Chesapeake is great, nice people and many interested places to go, plenty of jobs and vitality all around.
My choice is sailing in Maine and NS in the Summer and Caribbean in the winter. But that is just me.
I am old school. Integrity is to do the right thing even when no one is watching.