Southern Belle in Training

Fashion, Travel & Lifestyle Blog || Est. 2012 || Virginia Beach, VA

September 2, 2021

TRAVEL GUIDE: Ultimate Charlottesville VA Guide

     I'm so excited to finally share all of my Charlottesville recommendations in one place on the blog! I lived in Charlottesville for about three and a half years between 2018-2021. I am kind of in the minority for living in Cville in that I didn't attend the University of Virginia, or move to the area for a job associated with UVA. But despite that, I was absolutely charmed by the area, and had a great experience making Charlottesville my home for part of my 20s. Charlottesville is a great destination for a weekend trip for wine lovers, history lovers, food lovers, nature lovers.... it's true, Virginia is for Lovers! 

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About Charlottesville:

     Charlottesville is located very centrally in the state of Virginia- it's just over two hours north to Washington DC, and just over two hours south to the state line of North Carolina. It's located just east of the Blue Ridge Mountains, and it's only about thirty minutes to get to either Shenandoah National Park or the Blue Ridge Parkway. There are beautiful views of the Blue Ridge Mountains that can be seen all throughout the city. Charlottesville of course is best known for being the home of the iconic University of Virginia. While UVA is a big part of Charlottesville, it's not the only part. Charlottesville differs from other college towns in that the whole area doesn't revolve around the university- there are many neighborhoods that are completely separate from UVA. It's like the best of both worlds- it's both a cool college town and a separate small city!

     In addition to being known for UVA and lots of presidential history (home of Thomas Jefferson!), Charlottesville is also becoming increasingly popular as a destination for wine lovers. Many call it the "Napa Valley of the East Coast," and the Monticello AVA (American Viticultural Area) which surrounds the Charlottesville area is just bursting with wineries and vineyards. There is a charming and historic pedestrian district downtown that's filled with shops and restaurants called the Downtown Mall. 


    A lot of people are surprised to learn that Charlottesville has its own airport! It is very tiny- probably the smallest commercial airport I've ever flown into. But at this time it does offer flights from United, American and Delta, going to their various East Coast hubs. The Richmond airport is an hour and a half to the southeast, and Washington Dulles International Airport is two hours north. If you do fly, I would 100% recommend renting a car. Things are spread out in the area (especially the wineries), and while Uber does cover the downtown area, it won't cover a lot of the further away spots. Amtrak also passes through Downtown, and you can ride the train straight up to DC.

     However, if you're in the Southeast I'd definitely recommend driving to Charlottesville! It is definitely centrally located in Virginia, right off Interstate-64 and Route 29. You'll be so happy you have your car with you for exploring things like the wineries or mountains nearby. 


     For a small city, Charlottesville and the surrounding towns have a generous amount of lodging options! Something to be mindful of though is that lodging does tend to be expensive in the area. Prices get even higher during home game weekends for UVA football in the fall, and for graduation weekend in the spring. Out of the hotels below, the Hyatt Place, DoubleTree or AirBnbs would probably be the cheaper options. I also should note that while I haven't stayed at most of the lodging options listed (as I lived in the area),  I have scoured reviews for all of the hotels, and most of them I've visited at least once for food or drinks.

  • Quirk Charlottesville (499 W. Main St.) - Quirk is an artsy, boutique hotel that will definitely give you a one-of-a-kind stay, and it's less than a mile from the Downtown Mall. It's one of the newest hotels in Charlottesville, as it just opened in 2020. Quirk has a full art gallery that's open to the public downstairs, and upstairs it's home to the largest rooftop bar in Charlottesville. Even if you don't stay at Quirk, the rooftop is worth a visit. The original Quirk hotel is in Richmond- read my review of it here!
  • Graduate Charlottesville (1309 W. Main St.) - If you want to be in close proximity to UVA, this is the hotel for you! The Graduate Charlottesville is a charming boutique hotel located right on The Corner (UVA's downtown area). They also have a rooftop bar (although it is significantly smaller than the one at the Quirk hotel). Since this hotel is very close to UVA, if you don't want to be around a ton of students I would recommend staying here only in the summer months or during school breaks. But Graduate hotels are great! There is also one in Richmond that I've stayed at a couple times and really liked- read my review of it here!
  • Kimpton The Forum Hotel (540 Massie Rd.) - The Forum is a unique and upscale hotel that's located on the property of the University of Virginia. It's right next-door to the main building for Darden, the acclaimed UVA business school. If anything related to UVA is bringing you to Cville, this would be the perfect lodging spot due to its location! The guest rooms are very nice, and have an air of modern luxury. You can read my review of this hotel here!
  • Omni (212 Ridge McIntire Rd) - The Omni in Charlottesville is located at one of the ends of the Downtown Mall. If you're planning to spend most of your time exploring the city of Charlottesville itself and really want to dig into the local restaurant scene, this would be a perfect location! I attended a few work events at the hotel and had a great time- I presume the guest rooms are all super nice as well. 
  • Hyatt Place (2100 Bond St.) - The Hyatt Place is a few miles from downtown and UVA, located conveniently off Route 29. It's located within the Shops at Stonefield, a newer development of shops and restaurants, so there would be lots of things in walking distance from your room. I have had family stay here and they had a wonderful stay! The prices tend to be a little cheaper than hotels downtown or near UVA. 
  • DoubleTree (990 Hilton Heights Rd.) - I'm always a fan of DoubleTree hotels since they have their famous cookies for all guests, haha! Charlottesville's DoubleTree is located about 20 minutes from downtown/UVA, so if you want to be closer to these things it would be a bit of a hike. But since it's a bit out of town, it's very close to the airport, and also not far from a few of my favorite wineries. I had several work events here during the years I worked in Charlottesville and always enjoyed everything. The hotel also just recently underwent a major renovation so everything is super updated!
  • AirBnb (To be closer to wineries, look for locations in Crozet, Ivy, Afton, Barboursville) - Where hotels do tend to be on the expensive side in the area, you might be able to do better price-wise with an AirBnb. There are a good amount of them within the city limits of Charlottesville, but there are also many to pick from the in the small towns surrounding Charlottesville. Look for locations in Crozet, Ivy, Afton or Barboursville to be in close proximity to wineries and nature! AirBnb would also probably be the most economical option for a group to do. 

Eat / Drink: 

     There is no shortage of food and drink options in Charlottesville! For a small city, there are literally tons of well rated local restaurants, cafes and bars to enjoy. Similarly to the lodging options, a lot of the restaurants do tend to be on the pricier side (just being honest!). But there are some good affordable options mixed in as well. 

Breakfast/Coffee shops:

  • Bodo's Bagels (three locations) - This is probably the most iconic eatery in Charlottesville! Bodo's Bagels has a cult-like following. Not only are their bagels really good, but everything on the menu is also super affordable! I highly recommend the chicken salad sandwich on an onion bagel.
  • The Nook (415 E. Main Street) - A cute, old-time restaurant on Charlottesville's Downtown Mall. They're open for both breakfast and lunch, but I think the breakfast menu definitely steals the show. 
  • Paradox Pastry (313 2nd Street SE #103) - One of my favorite bakeries- they have a whole variety of delicious sweet and savory pastries. Located in walking distance to the Downtown Mall.
  • C'ville Coffee (1301 Harris Street) - Charlottesville has a ton of local coffee shops- if you're a coffee snob you'll find lots of places to enjoy! C'Ville Coffee was my personal favorite as I really liked their decor and ambiance (and they have a good variety of teas), but if you are into coffee you should also check out Mudhouse, Grit and Shenandoah Joe's. 

Lunch (or casual dinner):

  • Brazos Tacos (925 2nd Street SE) - This is my favorite casual restaurant in Charlottesville! Every time that I had friends visit, I tried to take them here for at least one meal. Brazos is very casual but the tacos are delicious. They specialize in fun varieties of tacos and they only serve tacos (they know what they do and do it well).
  • Tip Top Restaurant (1420 Richmond Road) - A diner style restaurant in the Pantops area of Charlottesville that serves breakfast all-day and a full lunch/dinner menu as well. 
  • Hot Cakes (Barracks Road Shopping Center) - A cafe with pretty good sized menu and lots of fun food options. Hot Cakes is a great spot for dessert- I highly recommend their fruit tarts. 
  • Blue Mountain Brewery (9159 Critzer Shop Road, Afton VA) - This is about 30 minutes outside of Charlottesville, but it's located very close to all of the Crozet and Afton area wineries, so stop here for a meal if you're out that way! They have an extensive menu and some of the best standard brewery/American fare in the area. 
  • Bold Rock Cidery (1050 Rockfish Valley Highway, Nellysford) - This is about 45 minutes from Charlottesville, but worth the day trip if you have the time! Bold Rock is the biggest cidery in the area, and they have a ton of great cider varieties. In addition, their Nellysford location has a full-service restaurant with great meals and appetizers! There are also lots of nearby breweries and wineries so you can make a day out of visiting this area.
  • Kardinal Hall (722 Preston Avenue) - This spot will always be special to me as it's where my going away party was before I moved to Virginia Beach! They have a large beer menu (and lots of other drink options as well), and a decent sized menu. I recommend their soft pretzels and the mac n cheese!
  • Dr. Ho's Humble Pie (4916 Plank Road, North Garden) - This is my favorite pizza spot in the area! The restaurant has a funny name, but the best pizza that I ever had near Charlottesville. They also have excellent desserts! This is across the street from Pippin Hill Winery- so if you're headed there for wine, definitely stop by for some pizza also.


  • Milan (1817 Emmet Street N) - My favorite dinner spot in Charlottesville! Milan has the best Indian food. They also often will throw in a free appetizer to sample or free dessert if you make a larger dinner order.
  • Monsoon Siam (113 W Market Street) - The top Thai restaurant in the area! Monsoon Siam is in a historic old home building a block away from the Downtown Mall, and both the inside of the restaurant and the patio make for romantic date night vibes.
  • Maya (633 W Main Street) - Maya is home to upscale Southern cuisine. Think of all your Southern favorites like biscuits, gumbo, pimento cheese and more, but served in fancy ways. Another good date night spot.
  • Bang! (213 2nd Street SW) - Bang! is an Asian tapas restaurant! It's best to get several small plates and share them with those in your party. I highly recommend the coconut rice. Bang! is also known for their craft cocktails.
  • Vivace (2244 Ivy Road) - This was my personal favorite in the area for homestyle Italian. Vivace also has a large and gorgeous patio!

Dessert / bars / misc.

  • Albemarle Baking Co (418 W Main Street) - The Princess Cake from Albemarle Baking Co is one of my all-time favorite desserts. I was lucky to have it at both my 25th birthday and my going away party!
  • Kohr Brothers (two locations) - Home of delicious frozen custard, with two area locations. If you haven't had it before, think the creamiest, most delicious soft serve ice cream ever. 
  • The Pie Chest (119 4th Street NE) - If you love pie, this is the place for you! The Pie Chest carries a nice variety of homemade pies by the slice.
  • Tillman's (406 E Main Street) - A great first date or happy hour spot! Tillman's is a wine and cheese bar on the Downtown Mall. As a cheese and charcuterie board enthusiast, I could never get sick of going here!
  • The Alley Light (108 2nd Street SW) - If you like speakeasy vibes, you have to try The Alley Light. It's Charlottesville's own speakeasy bar! I have to be honest, the vibe wasn't my personal favorite (dark and small), but a lot of my friends love this place. And I will give credit- the drinks here are great!
  • Tonic (609 E Market Street) - A newer spot near the Downtown Mall with drinks and a small food menu. Tonic has a lovely outdoor patio area with lights that's the perfect place to enjoy a drink outdoors in the summer. 
  • Quirk Rooftop (499 W Main Street) - Charlottesville's biggest rooftop! It's only a few stories up, so it's not as good of a view as you'd get at rooftops in larger cities, but it's still really nice. The Quirk Hotel is fun just to walk around and explore, and the rooftop has a good drink menu.

Restaurants I never made it to but have heard great things about:

  • Tavola (826 Hinton Avenue) - I've heard from many people that this is the best Italian food in Charlottesville, and a great date night spot.
  • Passiflora (422 E Main Street) - A new restaurant on the Downtown Mall that I didn't get a chance to visit before moving,  but have heard great things about. The food is described as being "Baja Mediterranean", and they have a very unique menu. 
  • Cake Bloom (705 W Main Street) - I am so sad this spot opened up right after I moved! It's a wine, cheese and cake bar- essentially all my favorite food groups!
If I had to pick just three restaurants from the list above as must-visits:
  • In order: Milan, Brazo's Tacos and Bodo's Bagels
{The famous Princess Cake from Albemarle Baking Co!}


     Visit local wineries - Aside from UVA, this is the main attraction in the Charlottesville area! Charlottesville is located right in the middle of the Monticello AVA (AVA stands for American Viticultural Area, aka a winery region), and there are 50+ wineries in Central Virginia!! Between 35-40 of the more prominent wineries are members of the Monticello Wine Trail. I'm proud of myself for visiting 30 of the Monticello Wine Trail member wineries in the three and a half years that I lived in Charlottesville! I can honestly say that I enjoyed at least something about all 30 that I've been to. Some have truly incredible wines, some have phenomenal views or beautiful tasting rooms. And some have all of that, and more! Haha. Since I lived locally in the area, I usually only visited one or two wineries at a time. But if you're visiting Charlottesville for a short time and want to try hit three or more in a day, I'd highly recommend booking professional transportation or a wine tour bus. Uber/Lyft don't reach a lot of the wineries that are further out, and you don't want to be stuck in an unsafe situation with having to drive after having wine all day. Check out Norm's Executive Transportation, Ambassador Limousine or Monticello Wine Tour and Coach Company for the full wine tour experience. Anyways, now for actual winery recommendations! To narrow it down a bit, here are my 10 absolute favorites. I have detailed blog posts for eight of these (which are linked), the only two that I don't are for Hark Vineyards and Septenary Winery. Hopefully I can someday write reviews for those two after trips back to visit Charlottesville:
    • King Family Vineyards - If you only have time to visit one winery, make it King Family. It's my favorite large winery in the area. Beautiful mountain views, great wine, and try to visit on a Sunday in the summer for Polo! You must try a glass of the iconic Crozet Rosé.
    • Glass House Winery - My favorite small, boutique winery. Glass House has their tasting room inside a tropical greenhouse! They also have a generous amount of outdoor seating by their beautiful pond. They employ a chocolatier who makes gourmet chocolates that compliment their wines. Glass House is also home to my favorite Virginia wine- the delicious Signora white blend.
    • Barboursville Vineyards - If you want Italian vibes in your winery experience, head to Barboursville. The beautiful views and architecture of the tasting room remind me so much of Italy. They have one of the largest selections of wine varietals in Virginia. Barboursville is also one of the oldest wineries in the state! Their wines are also some of the most affordable for the larger wineries. 
    • Septenary Winery - I'd recommend this one for a date as I think it's very romantic! They have a gorgeous outdoor seating area around a decorative pool of water, and mountain views. Septenary also doesn't allow children, so on weekends it tends to be a bit quieter than some of the family friendly ones. 
    • Merrie Mill Farm and Vineyard - One of the newest wineries, which I'm so glad that I got to visit before I moved. This wins the award for most Instagrammable tasting room! Merrie Mill Farm has a tasting room decorated like an art gallery. They also have a lovely outdoor seating area, and some fun small plates and appetizers on their food menu. 
    • Veritas Vineyards - Another one of the large wineries that is extremely popular! Similarly to nearby King Family, Veritas has great mountain views and a good assortment of wines. One of my closest friends in Charlottesville is the events manager, so I would enjoy visiting her at work! Veritas also definitely has the space outdoors to accommodate large groups. 
    • Pippin Hill Farm and Vineyards - Pippin Hill is probably the most well-known winery in Charlottesville, and seems to get a lot of publicity from outside the area. They do have the most beautiful view- probably one of my top three favorite views out of all the local wineries. The wine here is okay! I will say bottles and glasses are very pricy compared to some of the others in the area ($15+ glasses, $38-40 bottles). But I think Pippin is still worth a visit for the ambiance. It's also another good one to go to with a group.
    • Hark Vineyards - Hark has some of the most unique twists on classic wine varietals. Their Rosé has notes of strawberry, and the Chardonnay has strong flavors of pear and vanilla. All of their wines are creative and delicious! While their tasting room indoor space is still new and pretty industrial, they have great views outside. 
    • Reynard Florence Winery - This was my hidden gem little winery! A lot of my wine-loving friends had never heard of this one, but I definitely recommend a visit. My favorite spot of all in the area to sit and enjoy a glass of wine is under the pergola at Reynard Florence. They have a beautiful pergola with seating right in the middle of their grapes, and the view of the mountains is just spectacular! The owners of Reynard Florence also have two adorable corgis which love visiting with winery guests! 
    • 12 Ridges Winery - This winery is the furthest from Charlottesville and beyond the bounds of the Monticello AVA, but 100% worth the drive. 12 Ridges is the only winery located directly on The Blue Ridge Parkway, and it's currently the highest elevation winery in the state. They have 360 degree panoramic views of the Blue Ridge Mountains and the Shenandoah Valley! Plus, you get to enjoy a leisurely and beautiful Blue Ridge Parkway drive on your way. I highly recommend visiting in the fall. 

     Visit UVA Grounds - The historic University of Virginia calls Charlottesville home! Fun fact before we go further: UVA doesn't refer to their campus as a campus, it's called "Grounds." 😊 Now you know the proper local term! Anyways, Grounds is filled with beautiful and historic buildings, and it's worth a walking tour to see UVA! The Rotunda building is especially amazing to see. You can also spend a little extra time checking out the shops and restaurants on The Corner, which is across the street from Grounds and is UVA's own little downtown scene for students!

     Shop on the Downtown Mall - Charlottesville's main downtown area is a pedestrian district called The Downtown Mall. It's filled with local restaurants, shops, and a few small performance venues. I shared some of my favorite restaurant recommendations in the earlier section of this post, but I definitely recommend checking out some of the local shops. My personal favorite shop on the Downtown Mall is Darling boutique, an upscale consignment shop that also sells locally made jewelry and decor. 

     Explore Charlottesville murals and street art - Charlottesville is filled with beautiful murals and street art! I rounded up some of the most Instagrammable murals to see in this blog post

     Visit the Kluge-Ruhe Aboriginal Art Museum - If you're a fan of museums, this is a unique little hidden gem not to miss. The Kluge-Ruhe Museum is owned by UVA and free to the public to visit. It's the only museum outside of Australia that is 100% dedicated to Indigenous Aboriginal art. This is an ideal rainy day or wintertime indoor activity. 
     Tour Monticello - Monticello is Thomas Jefferson's famed home, and one of Charlottesville's most popular landmarks. It sits atop a mountain on the edge of Charlottesville, and the views from the top are incredible. I also have to give credit to those running Monticello today in how they portray the history of the enslaved workers that worked at Monticello. You learn a lot about the history of slavery in Virginia without it being glorified in any way (unlike other plantations or historic homes of the South). The springtime is a lovely time to visit Monticello as the gardens are in bloom!

     Visit Carter Mountain Orchard - Carter Mountain Orchard is an apple orchard literally located on top of a mountain!! It's the mountain next to the one that Monticello is on. There are some absolutely beautiful views from up here that are worth taking advantage of. Carter Mountain Orchard is open year round, not just in the fall! Honestly, I kind of prefer visiting when it's not apple picking season, as it does get very crowded in September and October.

      Float on the Rivanna River - The Rivanna is the main river in Charlottesville, and it's a perfect river for spending the day at for a leisurely float! Every time that I've floated on the Rivanna my friends and I have done a "DIY" float trip where we bring our own tubes and set up our own transportation (leaving half the cars at Darden Towe park and half of them at Riverview park), but the Rivanna River Company does tube and kayak rentals! They will take care of all the logistics for you.

     Hike Crabtree Falls - My favorite hike in Virginia!! Crabtree Falls is one of the tallest and most magnificent waterfalls in the eastern half of the United States. It is a steep hike to the top, but there are lots of places to stop to take a rest and enjoy the views. Crabtree Falls is located right off the Blue Ridge Parkway- it's about an hour south of Charlottesville.

     Polo at King Family Vineyards - My favorite summer event in Charlottesville! If you're visiting in the summer months, this is a must to attend on Sundays. There is a full-sized polo field at King Family Vineyards, and the Sunday afternoon matches are free to attend. There is delicious wine, food trucks, and you can also bring your own food and tailgate or picnic. It is quite the social event- I recommend getting there before 11am to get a good spot on the field! I got to go every year that I lived in Charlottesville, and some of my best CVille memories are from Polo Sundays.

     Winter sports at Wintergreen - If you're visiting in the winter months, I highly recommend a day trip to Wintergreen Resort! They are a full-service ski resort, and the gorgeous mountain views and winter atmosphere make you feel like you're hundreds of miles from Charlottesville, not just an hour away! Although I haven't had the chance to ski here yet, they also offer other fun winter activities. Snow tubing at Wintergreen is so much fun!! 

     I am pretty sure this is my longest and most detailed Travel Guide ever! I hope it truly showed off how many unique things there are to do in the Charlottesville area. I will always be thankful for the fun-filled three and a half years that I spent living and working in the area. Please feel free to email me or send me a DM on Instagram if you have any questions! You can also listen to my interview episode on the Like a Local Podcast where I share more about all of the spots listed in this guide. 

    And finally- a very detailed custom Google Map below with all of the places I recommended:

     God Bless,

     xoxo Annaliese


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