I've stretched my trip now to 5 days. How does Charlottesville compare with Charleston. Would a trip to just Richmond and Charlottesville be satisfying? Can it fill 4 full days?

I'll just say that I don't feel Charlottesville or Richmond can compare with Charleston or Asheville ... but then I'm a North Carolinian! :p

Any recommendations for a nice, well located, hotel in Charleston under $100?

Just a thought -- everybody and their mother will be on the road Friday PM since it will be a 4 day weekend for almost everyone. You will probably hit massive traffic delays on the NJ turnpike, thru the Baltimore tunnels. The mixing bowl South of DC (Springfield) down to Richmond will be a horror story.

You might consider leaving NYC at 3-4am and driving straight thru on Saturday morning.

Not going to find "nice" and "under $100" centrally located in Charleston (or pretty much anywhere else). But check tripadvisor.com -- they'll give you an array and map the choices for you.

Try priceline.

Trip advisor is showing availability at the Hampton Inn and Suites on Richmond Rd in Williamsburg for under $100. The Quality Inn Colony is inexpensive and located within walking distance to CW. Art and architecture can be found in CW and at the college of William and Mary www.wm.edu. The Wren building at W&M is the oldest college building in use. It was designed by Sir Christopher Wren.

A great Virginia architectual tour would start in Charlottesville with a tour of Monticello and then UVA and then continue to Williamsburg two hours away.

I see Richmond is between Charlottesville and Williamsburg. Would it make sense to base oneself in Richmond and make day trips to the other 2 and spend the rest of the time in Richmond? What's Richmond like?

They sound great, but I'm thinking I should save Charleston and Asheville for another time.

Given the short amount of time you have, saving Asheville and Charleston for another trip is probably a good idea.

I can't comment on Richmond, as I have only driven past it on the interstate.

But personally I'd stay overnight at each of the destinations you mentioned instead of driving back and forth from Richmond. Get a flavor of each place instead of an overdose of highway.

I want to avoid traffic so, taking someones suggestion, I'm thinking leave Sat morning 3am. Drive to Cape May , take a morning ferry to Lewes,MD. Drive to somewhere down the Delaware peninsula and spend Saturday and Saturday night there. Then drive to Williamsburg on Sunday and see Colonial Williamsburg on Monday. Any nice towns on the Delaware peninsula heading toward Norfolk?

I would stay right there in Lewes. Charming town.

To add to my previous post. Lewes has cute little shops in town and some nice restaurants. I like the Blue Plate diner for breakfast and lunch. It is just past the museum on the main road going out of town. There are also some outlets on Rt 1.
You could explore the area around Salisbury MD. The town itself isn't great but there is a nice decoy museum there. Search Salisbury for other ideas.
Further down the eastern shore is Chicoteague which might be worth a night. Quiet at this time of year, though.
You could head on down the eastern shore taking your time as you go.
Are you planning to spend Christmas day somewhere?

I don't think we'll stay in Lewes because I want to make some progress toward Williamsburg, but based on your input we'll have a look around, and probably eat there, before moving on.

As for Christmas day we have no definite plan. Maybe we'll be in Richmond at that point. I know everything will be closed but we can walk around and look for an open Chinese restaurant.

Any idea how long it takes to get from Lewes to Williamsburgh via the Cheasapeake Bay Bridge?

It is 4 1/2 hrs from Lewes to to Williamsburg so Lewes to CBBT is about 3 1/2. I was wondering about Christmas day because if I were you I would want to spend it in Williamsburg rather than Richmond or Charlottesville. Williamsburg is a Christmas destination so there will be more happening there than a city or town that will be very quiet. Even many local families walk down Duke of Gloucester street on Christmas Day. I can try to find some restaurants open that day if you are interested.

While I love Richmond (lived there one summer) and Charlottesville (spent a lot of time at UVA), neither can compare to Charleston.

It is just head and shoulders above Charlottesville, Richmond, and Asheville.

You'd be hard pressed to find better shopping, dining, attractions, history, and culture than Charleston.

I'm with GoT on this one. Given your criteria (cities with lots to see) and interests, I think Charleston the best choice.

If history showed up anywhere on your list, I'd say 4 days split between Wmbg, Richmond, and Cville would be a good plan (and I agree with Birdie that Wmbg is the better place to be Christmas Day).

Respectfully think that GoT has overstated the rankings, but agree -- as I said earlier -- that you're going to end up at Charleston.

Charleston sounds wonderful but being 12 hours away , it would take 2 days out of my 5 days just driving. I hope to get there someday, when I have more time.


Based on the Christmas in Williamsburg info, I may have to do some back tracking.

Saturday -
Leave NY (actually Jersey City) Sat morning 3am to avoid traffic. Get to Cape May by 7am. Take the 9:30 ferry to Lewes. Look around Lewes and have lunch. Make way down peninsula making stops in ??. Cross over CBB , drive all the way to Richmond. Stay in Richmond.


Sunday -
See Richmond museum of Art and some neighborhoods (Shockoe Bottom?)
Drive to Williamsburg and stay in Williamsburg.

Monday -
Drive to Williamsburg and see Colonial Williamsburg. Stay in Williamsburg.

Tuesday -
Walk around Williamsburg.
At night drive to Charlottesville.
Stay in Charlottesville.

Wednesday -
Go see Monticello. Look around Charlottesville. Drive back to NY.

--------------------------

Alternatively , If I don't want to backtrack I would stay in Williamsburg on Sat night. See CW on Sunday. See Richmond on Monday and Tuesday (Christmas).

-----------------------------

I am going to suggest an itinerary and just take what you like. Since you mentioned that you like cities and museums, why not turn this into a tour of small Virginia cities and their museums. Stop in Lewes as you planned and if you find the time you can drive onto Assateague from Chincoteague for a quick look. Continue down the eastern shore and across the CBBT to Norfolk where you can spend the night. Research on www.chowhound.com for a great restaurant. www.norfolkcvb.com shows accomodations. Visit the Chrysler museum the next day and walk around the area. www.chrysler.org Continue up I64 to Richmond and a trip to the Virginia Museum of Art. Then come back to Williamsburg for Christmas. You can sub Charlottesville in if you would like. Travel times are Norfolk-Williamsburg 1 hour, Williamsburg-Richmond 1 hour, Richmond-Charlottesville 1 hour.

Great suggestions Birdie.

For anyone who is a fan of photography, the Chrysler is currently exhibiting Cecil Beaton's Portraits which originated at London's National Portrait Gallery a couple of years ago. It's fantastic.