I have a small boat, and keep it on a smallish lake, so "where to go" is never an issue. When I go out for a three or four-hour daysail, being on the water and making the boat go are enough. If my crew is relatively inexperienced, I'll get on a comfortable tack, crack a beer, chat, eat a sandwich, wave at other sailors, mutter at jet skiiers, and enjoy the hell out of the day. If my crew is experienced and into it, we'll spend the day "actively" sailing: tend to sail trim, get every last fraction of a knot we can, feel and appreciate the responses from the boat, and enjoy the hell out of the day. It's all good.
If what I describe captures your fancy, Lake Anna isn't terribly far from D.C./Annapolis. Drop me a p.m. and I'll have you out some day.