I guess I'm kind of partial to Annapolis and Charlottesville since my children have attended schools in these cities. Annapolis is a wonderful, small city, with a lot of early American history, a great city-dock area, small shops and some good places to eat, and then there's the Naval Academy, which really is a great place to visit, especially if you visit when there's a parade march of the Brigade of Midshipmen. (If you saw the movie Annapolis, you wouldn't see the beautiful Naval Academy campus or Yard since the film wasn't filmed at the Academy.) The Naval Academy Chapel is truly a majestic and unusual place of worship and the new Uriah Levy Chapel, I'm told, is amazing. In fact, Commodore Levy, connected to Annapolis and Charlottesville, was an amazing historical figure too! C'ville has Mr. Jefferson's school, the University of Virginia, another great campus or "grounds," some very good places to eat nearby, and nearby Monticello. If you drive from the DC area to Charlottesville, there are various ways to get there; when traffic is light on I-95 South, generally between 10am-2pm, you can drive down to F'burg to its quaint old town, have lunch at Sammy T's or Merryman's, then head on Route 3 West (stopping briefly at the Chancellorville's Batttlefield site to observe the grounds where some truly incredible military tactics were carried out by Generals Lee and Jackson), and take Route 20 South thru some nice Virginia countryside to C'ville and Monticello. BTW, you can take the Skyline Drive out of C'ville.