Anonymous wrote:Definitely go to Monticello but get tickets now as they tend to sell out.

Lots of breweries, wineries, cideries. You will not run out of places to drink!

NP (hope you don't mind OP!)- Which tour of Monticello would you recommend? Thanks!

UVA is so prestigious.

Another good option if you're doing a big family group is to rent a house through Stay Charlottesville - they have properties all over town, including out towards the vineyards, and they tend to be significantly nicer and cleaner than your average Airbnb. Or try one of the bed & breakfasts at the wineries (Farmhouse at Veritas or the Inn at Stinson). The breakfast at the Farmhouse at Veritas is amazing and they do a great dinner with wine pairing (you can book the dinner even if you're not staying there).

For wineries, head to Pippin Hill or Veritas - both gorgeous views and indoor spaces with fireplaces. For restaurants The Local is great. And if you want to pick up some snacks / charcuterie nibbles to have back at your hotel/house, stop by Feast.

Definitely go to Monticello but get tickets now as they tend to sell out.

Lots of breweries, wineries, cideries. You will not run out of places to drink!

Another vote for Keswick. My husband and I used to spend a few days there over the holidays every year when our kids were little and it was magical. Also highly recommend Maya restaurant downtown. It's not on the pedestrian mall, and I can't remember if it's in walking distance of it but either way, totally worth going.

Stay away from the Omni.

It has seen way better days.

Quick or the Graduate.

Boar's Head Inn

When are you going? UVA’s Lawn will be all lit up for the holidays beginning this Thursday.

There are historical tours at UVA daily during the academic year - https://www.uvaguides.org/historical-tours/. Also, Monticello.

Lots of boutique and solid chain hotels on the downtown mall, which has lots of great restaurants, galleries, some shopping, a theater. There is a lot of live music at night.

Michie Tavern is an historic restaurant open for lunch.

Dozens and dozens of wineries and breweries within a 20 mile radius.

Humpback Rock is a good close-ish hike.

I prefer Keswick, which is more upscale, over the Boar's Head Inn. Both have golf courses and practice facilities. There are vineyards you can visit in the area, UVa to walk around, and Monticello. Not a lot else, as it's a fairly small town.

New poster. Is there stuff to do in December/January or is it geared towards better weather?

My husband travels there a lot. Stay away from the Hilton Home 2 Suites. He likes the Omni and the Residence Inn. There are lots of restaurants along the mall area as well as shopping, bookstores, etc.

Monticello isn't far, nor is James Monroe's house. Also lots of wineries nearby and hiking.
https://www.tripadvisor.com/Attractions-g57592-Activities-Charlottesville_Virginia.html

What is your budget? There are a number of hotels/bed & breakfasts on the Downtown Mall (pedestrian mall area with shops/restaurants). You could also stay at some of the hotels on The Corner which is at the edge of the UVA campus - some restaurants are located here as well. We generally stay in one of these two locations for ease/convenience. If you are looking for a luxury experience, I can recommend Keswick - it is a beautiful hotel but expensive and a little out of the way. Some people like staying at the Boar's Head Inn but I think it is dated and I don't particularly like it.

As for things to do, I would walk around the downtown mall, walk around the main campus of UVA, etc. There are also a lot of wineries in the area which are nice to visit.

We enjoyed the BobBoo speakeasy this summer, in addition to the number of wineries.

If you are interested in a driver for wineries, I find Norm's Taxi to be economical.

Hiking, wine, cozy places.

Meeting family (all adults) there for a long weekend. I have only driven through, and know nothing about the area! Is there a good downtown area w/restaurants and ... other things to do? Anyone have suggestions for where to stay and how to spend time? I tend to prefer hotel over AirBNB, but if no good hotels AirBNB is likely fine. Thanks!