Travel Journal: Charlottesville

My bestie planned a destination wedding and I love her for it. Liz knew she wanted a smaller wedding, which afforded her the opportunity to branch out when it came to venues. With guests coming from all over, Charlottesville was as central as anyplace and she found a gorgeous vineyard for her nuptials. I had never been to the area so I flew up a day early to explore and end my maternity leave with a bang. I wish I planned for one more non-wedding day because Charlottesville is cah-yute! And did you know there are 60 wineries in a 45 minute radius?! How has this city flown under my radar?


HOT TIP: Lindsay Silberman has a great guide here in case you want some additional travel recs.


Thursday, April 14th

I arrived in the afternoon and went straight to my hotel, an adorable b&b in the heart of the downtown area. I was going to try and rush out to explore the town for an hour before the stores closed, but when I checked in they told me there was complementary wine and cheese in the library and I said “screw sightseeing!” I made friends with some 60-somethings and got wine drunk while waiting for my friends to get into town. It was glorious. It was also a quintessential bed and breakfast type experience, which felt as core to my little weekend away as anything else.

After happy hour, I went to my room, showered up, and met up with Alissa. Together, we joined Liz, Damien, Virginia, and Kyle for drinks. We went to The Fitzroy, which is located right on the pedestrian mall. It was a great spot for slightly more upscale vibes in a college town.

Friday, April 15th

I woke up and grabbed a quick bite. This place really puts the breakfast in bed and breakfast. (I’ve probably made that joke before.) Everything is made in-house, including the granola, which is the same recipe served at Woodstock. The blueberry lemon bread was wonderful and I stuck an extra slice in my bag for later. After chugging some coffee I moved myself to the wedding hotel across town where I met up with Shea and Spencer for some touring.

Our first stop was Monticello, Thomas Jefferson’s plantation. The grounds are beautiful and we kinda snuck ourselves onto a tour of the house, which has been nicely preserved. There are some interesting quirks to the home and a tour of a house with all its knick knacks is a great [non-boring] way to get in a history lesson.

We didn’t linger at Monticello because we wanted to make sure we hit up at least one winery while we were in Charlottesville! Shea picked out Jefferson Vineyards since it was super close and we were able to do a simple tasting with snacks. We didn’t do a tour or anything; just enjoyed some good, reasonably priced wine in the sunshine. I highly recommend coupling Monticello and Jefferson Vineyards.

By the time we got back to the hotel, there was just enough time to throw on a new outfit before heading to our dinner reservation. I’m not sure how the group chose Public Fish & Oyster, but it was a good choice. Jules and I did an oyster shooter (nobody else joined…their loss) and the whole table split a bunch of oysters from the raw bar. The whole menu looked good, but I was very happy with my Hodgepodge (clams, mussels, oysters, shrimp, tomato, haricot verts, rice, lobster “Nantua” sauce served over rice). If you’re into seafood, this is a great spot.

After dinner, we all went to welcome drinks at Random Row brewery. While I mentioned Charlottesville’s wine scene, it should be noted that they’ve got a pretty good craft beer situation. If your group prefers growlers to grapes, you’ve got some good options, this being one of them. There was some really nice art on the walls that was available for purchase. I still kinda regret not bringing a piece home with me.

Saturday, April 16th

Everyone was moving a bit slow on Saturday morning so it’s a good thing brunch plans had already been made. We went to Tavern & Grocery, where I got the croissant sandwich because I basically needed a bacon egg and cheese to function. I also got a side of fries that was a mountain large enough for the entire table to share. The food here was good and it was in a good location, but the service was a bit spotty/slow.

After lining our bellies with coffee and grease, we walked the pedestrian mall. I wanted to pop into so many stores, but it was tough with a large group. This was also one of the longest commercial walkways I’ve seen, especially for a city this size, and I was a bit overwhelmed. There were sooo many bookstores. I was truly in heaven. While it may have been hard for me to pick stores to stop in, I had no trouble popping into a coffee and juice shop (Corner Juice), where I got one of each.

The main event! The wedding was Saturday evening at Early Mountain Vineyards. Anytime I told a local that’s where the wedding was, they sang its praises. It was, indeed, a picturesque setting and the wine was delicious. While I didn’t go to a ton of vineyards to compare, I would put this one on your list because 1) it’s got expansive views so it’s more than just a tasting room and 2) the meal was one of the best sit-down wedding meals I’ve ever had so I’m guessing this is where you’d find some of the best food to accompany your wine tasting. As for the vibe, there are lots of neutrals – this place really nails the Coastal Grandmother aesthetic that’s currently all the rage.

Finally, it was afterparty time! We all went to The Whiskey Jar for late night shenanigans. A dive with live music is all I can ever ask for.

Charlottesville Details
  • Accommodations:
    • 200 South Street Inn: This is where I stayed and it was absolutely lovely. If you go the bed & breakfast route, I always recommend choosing one that offers happy hour, breakfast, and is walking distance from the walkable part of town for peak quaintness. This place fits the bill.
    • Other Options
      • Dinsmore Inn: The other very appealing b&b in town. It was built by Thomas Jefferson’s master builder so it has some extra architectural appeal. It’s a bit pricier than 200 South Street but very nice accommodations.
      • The Draftsman: If you’re looking for a true hotel experience (e.g., fitness center) but want to remain downtown, this is a great boutique hotel near campus.
      • Quirk: The most Instagrammable hotel and it features an art gallery. It’s definitely pricier than most places in the area, but it’s très cute and has a good rooftop bar.
  • Food: I didn’t get to do all my own research when it came to restaurants and would love to have been able to dive into the scene a bit more. It seems like there’s a strong farm to table presence and local often means delicious. None of the places I went to were on any “best of” lists, yet I enjoyed every meal so I’m thinking the top ranked restaurants are probably pretty amazing. I would use this post as a starting point.
  • Activities:
    • Wineries: There are so many wineries and you can truly build an entire vacation around it. Lindsay Silberman’s travel guide (linked at the very top of this post) is great, but if you’re looking for additional inspo, check out this post.
    • Main Street: This is that pedestrian mall I mentioned. There are more than 120 shops and 30 restaurants so you could spend a lot of time strolling here.
    • Monticello: It’s nice to get in a liiiittle history lesson.
    • Campus: Charlottesville is home to UVA, one of the country’s oldest universities and founded by a founding father. I didn’t tour the campus but several friends did and they enjoyed themselves.
    • Golf: I’m not a golfer but the men in my life are and their interests were piqued by the golf scene in the area. If you’re not a golf person but traveling with someone who is, hit up the spa, pool, or Main Street.
    • Hiking: I would have loved to have tacked a hike onto my trip but didn’t have quite enough time. There are lots of trails and the views are sure to impress.
  • Tips:
    • Ubers are shockingly tough to come by so plan in advance, especially if you want to vineyard hop. We were encountering 20 minute wait times and canceled trips almost every time we tried to secure a driver. I don’t know how they’re not more prevalent in a town packed with college kids and a plethora of vineyards, two things that typically require a DD.
    • Because Ubers are few and far between, I recommend getting a driver and/or signing up for a tour if you’re looking to hit up more than one winery. Monticello Wine Tour seems like a very safe bet.
    • Between all the wineries and outdoor activities, I think Charlottesville is an ideal destination for a bachelor/bachelorette party or just a getaway with your friend group.
    • While I said I wished I had one more day, that’s really only because the wedding festivities took up a large chunk of time. Overall, I think 3 days (aka a long weekend) is plenty of time.
    • Late night food isn’t a big thing here. Much like the Uber situation, I was more than surprised to see almost zero options at 11 pm on a Thursday night in a college town. Plan accordingly.