Lots of marinas and a great liveaboard community in Annapolis, and I can make it from Annapolis almost to Dulles airport in VA in an hour at 6 am - maybe that's the upside of a down economy, fewer people with jobs so fewer commuters? There's a commuter bus direct from Annapolis to downtown DC that's very easy - takes about an hour but at least you can spend that time looking at something other than the brake
lights of the car in front of you. The other advantage of Annapolis is that when you're ready to go sailing on the weekend, you're only 10 minutes from the Bay.