I'd recommend eating at Bodo's Bagels EVERYDAY... get the Caesar and crush your breath like a local.
Kardinal Hall is a great place to hangout near the downtown mall, lots of beer taps and food...
The downtown mall is an outdoor streetscape for pedestrians with variety of restaurants, bars, and shops and an amphitheater at the end.
- Miller's, Jefferson Theater, Amphitheater has some DMB history but don't expect any prominent displays
- The Pink Warehouse is a block off the downtown mall (South Street Brewery is next door to it)
I highly recommend checking out the UVA Campus, particularly "The Lawn"
- The Rotunda is located here, Edgar Allen Poe's room is on display, and Jefferson's serpentine walls outside of the lawn host pretty secret gardens
If you are making the trip to Blenheim, perhaps consider stopping by Carter's Mountain for some views & apple picking / cider / occasional concerts
For Vineyards... I enjoy the scenery at Pippin Hill the most (it won't hurt to make a reservation for space), and King Family Vineyards is a good spot with lots of events (polo)
It's unlikely you'll have any DMB sightings while you're there but they do happen, I've seen members on my last 2 trips to Cville. It's EXTREMELY important to recognize that Cville residents leave them alone...
So be cool and stay calm should you see a member... a nod or low-key wave will do, let them approach you if they're in the mood. Just remember they are home, doing regular people things.
Have fun... not sure what the weather is like at the moment but Spring is a welcomed vibe. If the winter is longer it may be a bit grey with chilly weather and rains. Late Spring early Summer is peak VA for me