Itinerary from DC please
 

My wife and I are travelling from South Africa to attend our daughter's graduation at University of Virginia Charlottesville during May 2009. Besides spending a few days in Washington DC and possibly NYC, we're looking for ideas on how to spend the next 2 weeks. Any help will be very much appreciated.

Spend a couple nights in Annapolis, have a pint at Middletons Tavern, walk around, you will like it.

You could head down to visit Mount Vernon, Woodlawn Plantation, and Gunston hall--all fine old historic houses and grounds. Then keep going to Williamsburg for a glimpse of recreated American colonial living.

For a trip close to Charlottesville, I'd recommend a couple of days in Shenandoah National Park. They've got great scenery and hikes and there are two lodges in the park for accomodations.
For a destination outside of Virginia, I'd recommend Charleston, South Carolina and/or Savannah, Georgia. With some research, you could make it a great driving trip or you could fly to Charleson or Savannah and rent a car.

Are you willing to fly? Because really the whole country is open to you and with two weeks you would have time to see some nice stuff. What interests you?

I saw your other posts about getting from Dulles to Charlottesville, so am not sure if you will be driving from Charlottesville or not. I also don’t know if your interests are city or countryside. If you don’t want to drive, and cities are of interest to you, you can train from Charlottesville to Washington, and then on to NYC. The same train line would enable you to get to Philadelphia (before NYC) or Boston (after NYC), either of which would be very interesting and also quite lovely in May for walking and touring (Boston still a bit on the cool side, but very nice. NYC is very nice in May). You could also go south to someplace like Charleston, South Carolina or Savannah, Georgia (although these are longer trips, about 13 hours to Charleston and further to Savannah and some changes of train would be required, whereas NYC is 6.5 hours and no changes required). You could also go as far as Niagara Falls or Montreal, but with only 2 weeks, this may be ambitious. See Amtrak.com for schedules. I agree with the above poster that if you are open to flying, you really have a tremendous amount of options open to you. Charlottesville has a small airport, but via a connection you could get anywhere.

If you are driving, the Shenandoah area mentioned above is very lovely. I would also recommend a stop in Williamsburg and Mt Vernon on the way into Washington, D.C. Annapolis is a good stop on the way up to NYC. The St Michaels are of Maryland is really lovely as well and would be nice for a few days.

Get some guidebooks and do some reading, old guidebooks really don’t matter as sights don’t change that much over the years, you can then get updated ones for restaurants and hotels (and any new particular sights like museums.)

(Per your post on getting to Charlottesville from Dulles, I live in Hong Kong but grew up in the US, so sympathize with the driving bit. IMO using a vacation to “learn” to drive on the other side of the road is not really much fun. Moreover with your trip from Dulles, you will be alone, with jet lag and I think doing part of the drive in darkness, so really more worrisome. If you do this, remember that in the US, on roads with more than one lane of traffic in the same direction (like a highway) slow traffic stays in the right lane, and fast traffic passes on the <i>left</i>, so stay out of the left lane for a start….roundabouts will be confusing for sure….(what I told myself when I was learning to drive here was “keep the steering wheel in the middle of the road”, that helped to keep me on the correct side).

I think you should really consider flying from Dulles to Charlottesville, there are 4 daily non-stop flights on United Express from Dulles to Charlottesville, see http://www.united.com/. The flight takes less than an hour. Not sure if you have looked into this.

Just a caveat about the train from Charlottesville to DC - my son-in-law takes it periodically, and it is always, always, late -- sometimes by as much as 2 or 3 hours. So, it is an option, but not if you have to be somewhere at a certain time.