Amtrak between NYC and DC is annoying but at least it is a short ride. Amtrak don’t do assigned seating and Penn Station in NYC is pretty awful in general. Pay attention to the track listings which get posted about 10-12 minutes before you depart, to find your track quickly; trains are fairly full most times and if you’re last to board you might not be able to sit together. Or skip the seat and go camp out at a table in the cafe car which is what we usually do. You can have a table and power plugs.
Hotel recommendations in DC are really going to depend on your budget, as we are not known for cheap hotels in this town. In the more affordable selections I’d go for the Days Inn , in the 4400 block of Connecticut Ave NW (or thereabouts); clean hotel but not a lot of frills; good safe neighborhood, although quite quiet at night; about 2 blocks to the Red Line subway. In a slightly higher price range I’d look at Governor’s House on 17th and Rhode Island NW or Topaz Hotel on 17th and N, both are more boutiquey, close to the subway red line, in a fantastic neighborhood (DuPont Circle) which is safe but also has tons of restaurants, shops and nightlife. Upscale I’d do the W on 15th and Penn, or the Mayflower on Connecticut and N.
For a visitor I would *not* recommend staying in the suburbs. You can get some cheaper rates but you spend more time commuting in and out of the city and it’s just not worth $20-30 a day to spend 2 hours round trip on the subway (which is what it can take in the evenings if you have to change trains, just to get to Alexandria).
Subway: http://www.wmata.com/fares/smartrip/ get your SmartTrip card in advance as there is a $1 additional fee per trip to use a paper fare card on the subway. You can get the smarttrip card in most stations too but it’s just easier to buy it online. Subway will take you almost everywhere in the city worth seeing as a tourist. Our public transportation kinda sucks if you live here but it’s great as a tourist because most of the attractions are right on the subway line, whereas most people’s homes or offices are not.
Charlottesville/Williamsburg: skip the hotel and do a B&B, there are tons of them in the area and you can have a really unique experience without breaking the bank. Our favorite place in that area is actually about 20-30 minutes outside of Charlottesville http://www.tripadvisor.com/Hotel_Review-g58206-d734977-Reviews-Greene_Mountain_Inn-Stanardsville_Virginia.html (they have their own website which doesnt seem to be working currently)
-Have dinner at an Ethiopian restaurant. We have the largest Ethiopian community outside of Ethiopia, and the food is delicious, very unusual without being too weird, and generally pretty cheap. My favorites are Meskerem on 18th and Belmont, Zed’s in Georgetown, or Dukkem on 10th and U NW
-Go to Union Station and take a Duck Tour, which is on a WWII amphibious vehicle. The tour goes through parts of the city before it goes into the Potomac river for a mini-cruise. Buy tickets in advance as they are always full
-Live music at the 9:30 Club (http://930.com) or Black Cat (http://blackcatdc.com)
-if it’s baseball season, go catch a Nationals game!
-You may want to take a detour on the way out of town, after Mt Vernon, and go to the Udvar-Hazy Center, which is an extension of the Air and Space Museum, out by Dulles Airport and pretty impossible to get to without a car. The Space Shuttle Discovery is there!