The best way to get to Monticello is by car. It was a bit of a drive from D.C. but quite an enjoyable one. We passed through some beautiful farm land and vineyards along the way which were very picturesque.
I got around Charlottesville mainly on foot and by hired car. First I drove to Monticello Visitors Center, then to huge Monticello parking lot when I bought tickets and got in a shuttle which took me to the Jefferson's house.
Historic downtown is compact and easy to walk - the main street (the Mall) is closed for traffic. There is much space to park a car on a street. Watch for parkometers and get quaters ready. I paid 25c per each 30 min.
I reached University of Virginia (UVA) by car. Warning: it's difficult to find a place to park a car close to the university. I had to drive like crazy around some 15 minutes. The option is 30-40 min. walk from the historic downtown. There is also public transportation run by Charlottesville Transit Service (CTS) and other companies. This funny, green and old-looking bus in my picture is The Free Trolley and connects downtown with UVA grounds. Check the link below for more information.
To reach Michie Tavern, Ash Lawn-Highland and Jefferson's winery you definetely need a car.
I got to Charlottesville from Wahington, DC (National Cathedral - some 110 miles) catching some common in the late afternoon traffic jams in and close to DC. I drove I-66 East and took exit 43A to US-29 towards Charlottesville. The drive took me some 3 hours in total including two stops:
1. in Manassas Welcome Center (along I-66, some 5 miles before exit 43A); they are open 8.30 am - 5 pm but they used to leave maps and coupon books for accommodations outside when closed; I took some leaflets on my next Virginia destinations incl. Charlottesville, map of Virginia and coupon books for accommodations I used regularly on the way,
2. in The 29er Restaurant & Tavern in Ruckersville along US-29 and... it was the worst choice during my US trips, the food served there at very low price was not fresh and uneatable... never stop there.
In my coupon book I easily found my accommodation along US-29 4 miles north of Charlottesville downtown.