How to Navigate Charlottesville Wine Country

Travel blogger Alicia Tenise shares her Charlottesville Virginia Winery Tour Trip

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Hinge Straw Boater Hat, Nicholas Gingham Cold Shoulder Top, Mother Fray Step Denim

Keswick Vineyards Charlottesville Winery

Monticello Wine Tours Charlottesville

Horton Vineyards Charlottesville Virginia

The Best Charlottesville Wineries

Winery Tour Trips in Charlottesville Virginia

Gingham Cold Shoulder Top, What to Wear to a Winery, Rebecca Minkoff Midnighter Top Handle Bag

Top: Nicholas | Jeans: Mother Denim | Shoes: ℅ Hush Puppies | Bag: Rebecca Minkoff | Necklace: ℅ Taudrey | Hat: Nordstrom (Similar)

You guys have seen me chat about D.C. Wine Country in Loudoun County before on the blog, but Charlottesville Wine Country is only a 2-hour ride away from the District — and trust me, it might become your new favorite weekend getaway.

A couple of weekends ago before I left for Phoenix, my friends and I booked an Air BnB in downtown Charlottesville for the weekend and got to explore this wonderful city. I will give you a heads up, it is a little tricky trying to secure a hotel in the spring since Charlottesville has a lot going on this season, but if you’ve got a larger group, an Air BnB is the way to go!

The wineries out in Charlottesville are anywhere between 15 to 40 minutes outside of the city, so I would suggest planning accordingly to maximize your time! Another thing I would suggest? Leaving the driving to someone else! We decided to book Monticello Wine Tour for our trip, and they did not disappoint!

At first, we had a wishlist of three wineries that were highly recommended to us, but we had no idea that those wineries we picked were super far away from each other. Our driver, Anna (who you should definitely request!) emailed us days before our trip and suggested a few wineries that were closer together so that we could maximize the five hours we had in our car. Ultimately, we ended up going to Horton VineyardsBarboursville Vineyards and Keswick Vineyards. The photos you see here are from Horton, but pretty much every property we visited that weekend was stunning!

You can book a car that holds up to 14 passengers with Monticello Wine Tour, and they also provide airport transportation to and from Richmond, Dulles, BWI and Reagan in case you’re not local and want to fly in for the experience (trust me: this is the East Coast version of Napa, so I would highly recommend checking it out!) All in all, just be safe and book a car for your next Charlottesville winery tour — it will make your experience far more enjoyable!

P.S. — I never post photos of my friends here, but here’s what part of my squad looks like! You can snag my dress here.  


  1. Looks like you guys had a blast!

    Posted 5.4.17
  2. Sarah wrote:

    The wine is my favorite part about living here! I love Barboursville – other good ones are Flying Fox, King Family, Veritas, Cardinal Point… Let me stop…. The amount of wine I drink is showing!

    Posted 5.4.17
  3. Jenny wrote:

    Sounds like so much fun! I love going to wineries. It’s aways such a fun time.

    Posted 5.4.17
  4. I have never been to a winery. Your photos are lovely.

    Posted 5.5.17
  5. Liz wrote:

    I absolutely love the look of your dress and shirt – so great! I need something like this in my wardrobe this year!

    Posted 5.5.17
  6. Brooke & Meggan wrote:

    definitely on my bucket list and you look so pretty!

    Posted 5.9.17
  7. Elizabeth Oliveto wrote:

    Looks like such a fun time!
    Xo, Elizabeth

    Posted 5.10.17
  8. Your outfit is just perfect for the wine country…you nailed it! That bag has been on my Spring wishlist, not gonna lie. 🙂 You are gorgeous and I always enjoy your posts!

    Posted 5.10.17
  9. sandyalamode wrote:

    SUCH a perfect winery-visit outfit! I love it, and loving the gingham!

    Posted 5.10.17
  10. This looks like such a fun trip! Wine country sounds AMAZING!

    Mindy II

    Posted 5.10.17
  11. Megan wrote:

    I have been meaning to go on a trip like this! Wine country is so much fun and your gingham top is so stinkin cute!

    Megan |

    Posted 5.10.17
  12. Tomi Obebe wrote:

    I’m glad you linked that dress because I am OBSESSED.

    xx, Tomi

    Posted 5.10.17
  13. Sara wrote:

    loving this travel recap!

    Posted 5.11.17

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