Want Claire’s entire guide to Charlottesville + Virginia Beach? Check out her PDF!

My family has quite a bit of history in Virginia, so it’s a little surprising that the only time I’ve visited prior to this was on an 8th grade field trip to Washington D.C. to learn about places like Monticello and colonial Williamsburg. This time around, Craig and I went for a long over due visit with family and to see a bit more of the state. If your next trip to Virginia takes you to the Virginia Beach area and Charlottesville, here are a few suggestions for what to eat, see and do while you’re there!




A long weekend felt like plenty of time to make our way around each of these areas of Virginia. Although, Craig and I did discuss a fantasy scenario we both had about staying longer to do a Civil War road trip. This is deeply embarrassing (nerd alert!) but something we actually do hope to make a reality someday.


We came for a long overdue visit with family but honestly, it’s such a unique and cool area of the country, it’s totally worth experiencing even if you don’t have any connections here. We started our trip in Franktown, which is about a 45 minute drive from Virginia Beach. This is a great destination for a half-day trip because of the oyster ships and tasting shacks along the coast here. The area is known for having a large variety of oysters, second only to the hudson valley in terms of production, historically speaking. And while the oysters here were a bit on the large side for me, they tasted super briny and delicious! The scenery here is also really beautiful. We did quite a bit of driving and all of the highways run over water and it’s a bit like being in the movie “Waterworld”. As you make your way between the countryside and Virginia Beach, you’ll drive past quite a few shops and bed and breakfasts. We didn’t get to stop at any of them but it seemed like a fun way to spend an afternoon, especially if you stop off for a bottle of rosé and just bop around shopping for antiques and eating oysters.


We stayed in an Airbnb in the Cape Charles area, which is one of the southern most towns along Virginia’s Eastern shore. The area has a main thoroughfare where the boardwalk is and there are a bunch of hotels if you’d rather go that route. Honestly though, I recommend renting a cute Airbnb (Think: 1900’s bungalows, so charming!) in a relatively walkable area with some cute surf shops, restaurants, and boutiques. Virginia Beach has a nice east-coast surfer vibe in the hipper areas, but it has a Jersey Shore vibe in the not-so-hip areas, so take a look at what’s near by before you book.


ROOST // 501 Virginia Beach Blvd., Virginia Beach, VA 23451

There’s a great gift shop right next door to Commune (see food + drink section below), and it seemed like the perfect place to get a housewarming gift from. So many lovely home decor items, candles, plants and the like to choose from.

NORTH END BAG CO. // 607-B 19th St, Virginia Beach, VA 23451

These handcrafted bags are gorgeous and super durable. The shop is really charming and located in the same area as Three Ships Coffee (above) and they have a nice variety of canvas bags and masculine leather goods.


One word: Oysters! We ate our weight in oysters while we were here and you should do the same!

BAYFORD OYSTER CO. // 5513 Bayford Road., Franktown, VA 23354

This place has been around since the beginning of the 1900s and oysters are serious business here. This was one of our first stops in the area and it was such a good time. They had such a lovely variety oysters to try and everything was delicious.

COMMUNE // 501 Virginia Beach Blvd Suite b, Virginia Beach, VA 23451

This lovely little spot is located within a larger complex along Virginia Beach Boulevard that we really loved. We had breakfast here and fell in love with their lavender lattes, sourdough croissants, and the eggs Benedict! It’s a fantastic brunch spot, so definitely check it out and come hungry!

ESOTERIC // 501 Virginia Beach Blvd Suite a, Virginia Beach, VA 23451

Don’t let the name fool you, this place isn’t esoteric at all, in fact, it’s quite lovely and I think most people would agree! The focus here is on seasonal, Virginia cuisine and using ingredients that are all locally sourced. They actually have a giant backyard garden that’s beautifully taken care of and they grow everything right there to use in their kitchen. Brian Wegener, is their Executive Chef and a major up and coming chef in the Virginia culinary scene.

THREE SHIPS COFFEE // 607 19th St, Virginia Beach, VA 23451

This coffee shop is pretty close to the other spots I mentioned that we liked on Virginia Beach Boulevard, but it’s in it’s own little area. They have the best coffee and they roast it right here! You can actually see the roasting in action if you stick around for a bit.

BOTTLECRAFT // 1560 Laskin Rd #156, Virginia Beach, VA 23451

One thing people might be surprised to hear is that Virginia Beach has a really fabulous wine industry! Wine has been being made here ever since the beginning of settlement. Even folks like George Washington and Thomas Jefferson grew grapes for this purpose. And this place is not only a bottle shop but also tasting room where you can try some fun, local varietals. They have a great selection of beer too, if that’s more your thing!

PACIFICA // 214 40th St, Virginia Beach, VA 23451

It’s a little hard to tell what this place is just by looking at it from the outside, but inside it’s a cozy bistro serving up tapas and the most delicious cocktails! If you’re in the mood for some fireside cocktails with funky, interesting flavors, this is the place. Fun fact: the bartender here, Jimmy, prides himself on making his own hot sauce and his hot sauce martini comes highly recommended! They also have a nice beer menu, if you’re not interested in cocktails.

BAY LOCAL // 2917 Shore Dr, Virginia Beach, VA 23451

Come here for the insane Bloody Mary, stay for the shabby chic decor and charming atmosphere! This is another one of Virginia Beach’s best bunch spots, and the Bloody Marys they serve here are huge and come with a huge shrimp cocktail type garnish. The food is great too but it’s packed with locals so try to avoid going on a Sunday morning if possible because there will be a long wait.


Charlottesville is about a 3 hour drive from Virginia Beach and it’s a darling little college town with plenty to see, eat and do. It’s super lush and pretty during the end of the Summer months but it was also really humid, so dress accordingly! Monticello and Carter Mountain are both located right outside of Charlottesville, and they’re both fun spots to visit while you’re here. Carter Mountain is a great place to go apple picking in the summer and early fall. It’s a local tradition here and actually tons of fun (cider and doughnuts, anyone?). Right next door you’ll find Monticello, Thomas Jefferson’s historic home. This property is just beautiful! As you can imagine, there are lots of gardens to walk through and you can take guided tours, as well. It’s interesting to see Monticello for yourself and learn about the history here. I recommend doing a bit of research before you come so that you have a good sense of how emblematic this place is of Virginia, especially as it relates to the broader U.S. tapestry.


We stayed  at The Graduate, that was located in a young and hip area, but it still felt like parents could stay there for graduation and enjoy it, as well. They had fantastic coffee in the lobby, old portraits, things like that. Quite hip! Another plus, it was walkable to everything. We give it two thumbs up.


MELODY SUPREME // 115 4th St SE, Charlottesville, VA 22902

This hipster record shop is located right on the main campus tract.

LOW VINTAGE // 105 5th St SE, Charlottesville, VA 22902

This place had a wonderful selection of carefully curated vintage clothing and accessories, plus, they sell vinyl, too! Lots of perfectly worn t-shirts and leather jackets, boots, and vintage frocks galore.


This store is so cute and has a big patio that will be filled with shoppers on Saturday night. Right near by here is an independent neutral separates boutique that you’ll definitely want to check out if that’s your thing!


MAS // 904 Monticello Rd, Charlottesville, VA 22902

This Spanish restaurant is known for their tapas, and I can see why! Everything was really delicious. I recommend the Paron cocktail, it was so good! The decor is industrial inside with brick walls and vintage light fixtures and there’s a big outdoor with lots of tables with umbrellas.

BEBEDERO // 225 W Main St, Charlottesville, VA 22902

This is a lovely Mexican restaurant with a modern menu and an insane amount of tequila options! The margaritas we had here were delicious, but I don’t think you can go wrong, no matter which cocktail you pick. They’re open for brunch and dinner and have live music around dinnertime most weeknights.

C&O // 515 Water St E, Charlottesville, VA 22902

This was our best meal of the trip by far! I fell madly in love with the fresh squeezed greyhounds they serve here. They were so insanely good. We also had the steak with ginger sauce, which makes no sense but it really worked! This place has been here for over four decades. It’s located inside a historic brick building with lots of vintage character (think: shutters where old doors and windows used to be and a large tin sign out front that reads “Restaurant”). The inside is like a maze, with six different dining areas and dark and moody lighting—being a server here would be tough! It’s not particularly formal because lots of college kids come in but it seems like a great place to bring your parents or a date. We sat downstairs in the bar and loved it. Besides the steak, we ordered the gnocchi and duck confit and the pudding. Everything was so delicious and I loved that they had perfectly salted butter to go with the table bread. We also had the red snapper sweet corn salad, which was so fantastic. All of the sauces were great, too! As far as cocktails go, I adored the greyhound, but we also tried the Haute Hoot, which was kind of like a Negroni but the compare was steeped in dried chili and coffee beans. It was really interesting! Overall, this place is definitely worth a visit. Everything was top notch.

THE VIRGINIAN // 1521 University Ave, Charlottesville, VA 22903

This bar is right by campus and has a fun ambiance, and gives you a great feel for the college scene. It also happens to be one of the oldest bars in town, open since 1923. It has a rustic feel, with lots of big wood boothes and tin-tile ceiling. The menu is mostly diner-style comfort food.

BEL AIR MARKET // 2401 Ivy Rd, Charlottesville, VA 22901

This is a gas station market with really yummy gourmet sandwiches. Scoop some up for a picnic!

CHAPS ICE CREAM // 223 E Main St, Charlottesville, VA 22902

This cute 50’s style ice cream shop is walking distance from the Melody Supreme record store I mentioned above. They make all of their flavors in house and have been here for decades. Everything we tried and ordered was so delicious. Birthday cake flavor, and cherry flavor were our selections, and they both turned out to be fantastic choices. Get yours in their homemade waffle cone!

BLUE GRASS GRILL & BAKERY // 313 2nd St SE, Charlottesville, VA 22902

One word: biscuits. The biscuits here are so giant and fluffy and delicious! This place has been serving up hearty southern comfort fare since 2001, and they bake all of their own breads, biscuits and pastries in house from scratch. Come for brunch, you won’t be disappointed.

THE PIE CHEST // 119 4th St NE, Charlottesville, VA 22902

This place is known for it’s local, seasonal pies and they’re really good! Bourbon pecan, spiced pear, and the pumpkin pie all looked delicious! They also had a fun selection of savory pies, too, with offerings like classic chicken pot pie, pulled pork pie, and even a meatball pie. Everything was super fresh and tasted like they used high quality ingredients. Stop in for a slice and if you order something sweet, get it a’la mode.

BLUE MOON DINER // 512 W Main St, Charlottesville, VA 22903

This place offers eclectic diner food in a folksy atmosphere. The big draw is that they serve breakfast all-day. Everything was really great but I highly reccommend the grits, they were so good here!

BANG! //  213 2nd St SW, Charlottesville, VA 22902

This is an Asian-fusion, small plate concept spot that’s actually a renovated house. It’s a fun, cozy spot and great if you’re in the mood to share and try a little of everything!

CONTINENTAL DIVIDE // 811 W Main St, Charlottesville, VA 22903

This is a casual tex mex spot that offers a fantastic array of margaritas! Between sips, order the ‘Red Hot Blues’ nacho dish! It’s interesting and delicious. You’ll know you’re there when you spot the neon sign out front that reads, ”GET IN HERE”.

TAVERN & GROCERY // 333 W Main St, Charlottesville, VA 22903

This is a cute shop with cheap groceries. Pop in for a quick bite to eat or a happy hour cocktail, then grab some picnic supplies to-go!

PIPPIN HILL FARM & VINEYARDS // 5022 Plank Rd, North Garden, VA 22959

This place is super fancy! There was actually a wedding happening while we were here so it was extra booshie. There were lots of ladies in maxi dresses with big hats and big sunglasses on, day drinking. Other than that, they did have a nice selection of wine/ The whites and rosés were good and the grounds are so pretty, it’s a nice place to spend a day.

DAVE MATTHEWS WINERY // 31 Blenheim Farm, Charlottesville, VA 22902

This is by far the most Virginian thing we did. After a stop in at Pippin, we headed here! The wine was fine but what we loved about this place is that everyone brought their dog! It felt like we were hanging in someone’s backyard, like it was a garage turned winery. It was very different from Pippin. Lots of fun and the dog watching was fantastic. Food trucks park here and it is a fun way to spend a day.