A Successful Long Weekend Trip to Charleston, SC

16 min read by  •  Time Visited: End of June 2019

My boyfriend and I had been talking about taking a trip to Charleston for a couple years now and we finally made it happen! After a busy spring with moving in together and starting new jobs, we were overdue for a long weekend away from it all. We realized that we hadn’t traveled together since our month-long Europe trip last fall. It’s amazing how quickly time flies by! We liked the idea of traveling somewhere we could drive to, have previously enjoyed visiting Savannah for its Southern charm, and have heard rave reviews about the up-and-coming restaurant scene in the city. Fortunately, it exceeded expectations and we can’t wait to go back! Keep reading to see how you can have a successful long weekend trip to Charleston.


We began our 6-hour drive to Charleston on a Thursday morning. On a drive longer than four hours, I always think it’s nice to stop for a break; ideally a meal somewhere. I found Skippers’ Fish Camp Oyster Bar & Grill in Darien, GA, which was close off the highway and highly rated for it’s seafood and Southern menu. Between the two of us, we got the crab cake appetizer, sweet potato souffle side, fresh catch mahi mahi blackened sandwich, mac & cheese, and sweet tea. How predictable?!

Where To Stay in Charleston

Once again, we chose to stay at an Airbnb. When do we not?! It’s by far our favorite choice for accommodations regardless of the location. The Cozy Art Villa was located a few blocks away from Upper King Street. It was quiet, had local spots steps away on Spring and Cannon Streets, and yet was only a 5-minute walk to King Street. In fact, most of our favorite spots were located on the upper end of King Street anyway.

I would rate this unit a 7.5/10. It was clean, bright, had a super simple self check-in, a parking spot in the driveway, modern bathroom, nightstands on both sides of the bed, a full length mirror, a fan in bedroom, and thoughtful touches like snacks, beach towels, an umbrella, and an iron & ironing board. Our complaints were that it was noisy in the unit above us (the stomping/walking sound more than anything), the bed was very firm, and the street itself was a teeny bit sketchy. We didn’t feel unsafe, but maybe I would have if the neighbors were out in the street and I was alone at night. A few things you should also note are that it is definitely a small unit that I would recommend for no more than two people. The kitchen is also very minimalistic – a mini fridge, a small sink, and a microwave. A perfect size for us though given we are hardly in the unit. We’re always out exploring!

Where To Eat & Drink in Charleston

The main reason we travel and probably the main reason you visited this blog — to experience the city and the local culture through great restaurants and bars. From casual to upscale, beer to cocktails, downtown to the suburbs…the places we loved, want to try more from, and felt disappointed by are all detailed below.


For the first time possibly ever, we didn’t make a single reservation or have any set plans. It was just the two of us, exploring and loosely following my list of research in Google My Maps to match whatever we were in the mood for or intrigued by in that moment. It’s much more relaxing to travel in pairs because we can always seem to find two seats together at the bar no matter how big or small, popular or unpopular the place is, so that is exactly what we did. We sure met some characters and fun bartenders along the way, too!

The Perfect Way to Wake Up

Callie’s Hot Little Biscuit

The place that always has a line (at both locations), but is worth every minute of it. The sausage, pimento cheese and scrambled eggs on a biscuit was seriously incredible. Best ever status, hands down. Plus, it’s local to Charleston. You can’t miss it! You can get anything from flavored biscuits to biscuit sandwiches to biscuits with homemade jam, or even packs of biscuits and pimento cheese out of the case to-go. Be warned, it is messy and seating options are little to none!

Kudu Coffee & Craft Beer

This local spot off of King Street is a coffee shop by day, craft beer bar by night. I loved the vibe here — a bright, open space in an old house filled with locals, two small bars at the counter, people working on their laptops, and groups gathered on the outside, shaded courtyard. I ordered the iced green mint tea and it was very refreshing!


For Fellow Oyster Lovers

My favorite section! All of these places were amazing in their own way.

The Ordinary

As soon as we arrived and checked into our Airbnb, we headed straight to The Ordinary on upper King Street, a close walk away from our Airbnb. During their happy hour from 5pm-6:30pm weekdays only, all oysters are $1.50 each. I prefer the $1 deal at other places, but they happened to have a fantastic selection of high quality oysters made up of a mix of local and northeast oysters from petite to XL size. Although the assortment is ever-changing, we tried the Savage Blondes (my boyfriend’s favorite), Single Ladies, Sea Clouds, Uncle Bobby’s, Masonboro Salts (my favorite), and Katama Bays. They had an unusual cantaloupe mignonette, red wine mignonette, horseradish and an incredible (all time favorite) lemongrass cocktail sauce. The vibe, you ask? A pretty perfect introduction to Charleston — a restored 1920s bank with high ceilings bustling with high energy and a well-dressed crowd.

The Darling Oyster Bar

After having this spot on my list and passing it time and time again on King Street, we showed up at 4pm when they opened to ensure we could get a seat without having a reservation. I kid you not, the place was full by 4:45pm! They offered happy hour on their gulf house oysters only, but they were still tasty. The best part was we actually sat at the oyster bar and watched the crew shuck each and every one…nonstop. We also ordered the octopus and cold potato salad and the lobster roll. I haven’t had a lobster roll in far too long, and it was SO incredibly tasty — the perfect amount of lobster chunks, not too heavily dressed, not too many “filler” ingredients in the lobster mix, and a nicely toasted, pull apart, rich brioche bun. Nom nom.

Leon’s Oyster Shop

We debated heading farther north on King Street but I’m so glad we did for Leon’s; a rustic yet award-winning Southern and seafood joint located in an old auto shop garage. They don’t serve oysters on happy hour, but they had a comparably impressive selection to The Ordinary. We ordered our favorites, the 2-piece fried chicken (you pick if you want white or dark meat), and best of all, frozen gin & tonics. A much needed refresher after a sweltering walk north! They also have rosé on tap, if that’s more your style. I was super impressed by the fried chicken and appreciated that you could order such a small amount. Apparently it was so good because it’s brined, glazed in Old Bay, and fried in lard. Oh my!

Needless to say, we each had at least a dozen oysters per day!

Superior (and Less Superior) Sips

To make things interesting, I’ve put these in order from my favorite to my least favorite. Well, maybe the first two are tied. I can’t decide! They’re just so different…

Felix Cocktails Et Cuisine

Creative cocktails and small plates with a Parisian flare is the draw at this attractive bar and restaurant on Upper King. We sat at the bar at an off-time, talking to the bartender nearly the entire time over some of the best drinks we had on our whole trip. My boyfriend loved their gin old fashioned, and I opted for the El Burro made with tequila, creole shrubb, ginger beer, pineapple and fresh lime juice… a mule of sorts. They also offer “bartender’s choice” drinks to make you something creative off-the-menu. She made us one with Pavan french liqueur (the most beautiful bottle) that made me want nothing else ever again. Although we didn’t eat here, the raclette burger sounded and looked pretty epic.

The Cocktail Club

This speakeasy-like cocktail bar located up a set of stairs next to the Macintosh restaurant has it’s own Charleston spin to a typical speakeasy. It’s housed in a reimagined 1881 building in the coolest way possible. The drinks were top notch, too. Although on the spicy side, which is unusual for me, the Double Standard cocktail made with house-infused serrano gin and cucumber vodka blended with ginger, cilantro, lime juice and celery bitters was delicious!

The Rarebit

This uncomplicated, modern American diner is famous for their Moscow mules and comfort food. It was a bit of a trend you’ll find here in Charleston. Every place seemed to make their own ginger syrup/beer or have it on tap. And the comfort food, well, don’t act so surprised. Southern food is comfort food most of the time! Anyway, the mule proved to be very enjoyable.

Citrus Club at The Dewberry Hotel

On my trip wishlist was to visit one of Charleston’s rooftop bars. We chose this 8th floor terrace and lounge, which happens to be highest rooftop in the city! Quite a difference from my NYC days. As you might expect by the name, the vibes are tropical, colorful and preppy. Given its location within a luxury hotel, you check in at the host stand in the lobby and then are escorted up the elevator. We ordered the Longtime Listener and Mr. Nice Guy cocktails. To be honest, they were a little too sweet for me and expensive, but the atmosphere and view were totally worth it!

The Gin Joint

This intimate, speakeasy-style cocktail bar had everything going for it. It was a charming yet cool spot, busy but not so busy that we couldn’t get a table right away, and had a large menu of cocktails. I went with the Athena’s Rule cocktail with Feta Infused Ford’s Gin, Green Bell Pepper, Lemon, Rum, Aquavit, Genepy des Alpes and Black Olive, which I completely understand appeals to a very small percentage of people, but I was intrigued by how weird it was. It was decent, but I wouldn’t order another one. Where things really went downhill was when my boyfriend opted for the Bartender’s Choice, where you choose two from a list of refreshing, tart, savory, etc. After quite a long wait, the server brings over the drink with zero description. I’m sorry but if you get a mystery drink, I think you deserve to know what’s in it! It also hardly fit his description, and was a liquor he probably wouldn’t have chosen. In hindsight, it’s worth mentioning up front your liquor preference(s), but the whole experience felt rushed. Oh well…

View from Citrus Club Rooftop

Classic & Fresh Bites

The Macintosh

I was originally drawn to The Macintosh for their $5 happy hour from 5-7pm, brunch menu with supposedly an amazing biscuits and gravy, and their popular bone marrow bread pudding. Instead, I ended up ordering the Blue Velvet cocktail with Miles gin, blueberry, lemon, mint and ginger, Pickled Shrimp appetizer with watermelon, radish, asparagus, benne seed, candied lime, and a side of Pecorino Truffle Frites. Everything was tasty but, no surprise, the truffle frites were probably my favorite! I think this spot is a classic, reliable, modern American restaurant that may never blow you away but will always be good.

Basic Kitchen

This bright and airy restaurant focuses on seasonal, local produce and ingredients in its dishes to serve nourishing dishes and drinks. We ordered the Miss Paula’s Shrimp Ceviche with local shrimp, South Carolina peaches, avocado, and Charleston local Mitla tortilla chips. I loved everything about it except it really needed salt! We quickly became friendly with the bartender who served us an off-the-menu cocktail with gin, matcha, passion fruit, lime and chartreuse. It was great! He kindly gave us some local recommendations too, which you’ll read about below (see: Burwell’s).


Charleston Southern & Steak Staples


Notorious for booking out all reservations far in advance, we decided to visit The Bar at Husk next door instead.  It’s housed in an old kitchen building of the Victorian-era home, where the Husk restaurant is. We loved the local, welcoming feel paired with great service, cocktails and bar bites. We ordered the Southern Cheese Board with homemade jam and bbq peanuts, and I had the Strawberry Hill 11 cocktail with strawberry and sage infused vodka, ginger beer and lime. Do you see a theme here? Mule cocktails are everywhere in Charleston! I’m sure there are better things to order here, but it was what we were in the mood for at the time. I hope to try the Husk restaurant next time!

Poogan’s Porch

Next door to Husk on the cobblestone Queen Street is a step back in time at Poogan’s Porch. Since opening in 1976, it’s become a Southern institution serving a fresh approach to Lowcountry cuisine.
Since it is equally popular as Husk, we opted to sit at the bar. We ordered the Pimento Cheese Fritters and Fried Green Tomatoes with goat cheese, peaches and peach chutney, and spiced pecans. They were yummy, but after a long day of hopping around, eating and drinking, I wished I didn’t end with two fried menu items.


Some of the best places are the biggest surprises, and this was that place! Burwell’s calls themselves a modern twist on an old school steakhouse, which I think describes it perfectly. It was recommended to us by the bartender at Basic Kitchen, who had previously worked here and knew the bartender working that same night. He told us to go see Jojo, order the Moscow Mule, Wagyu Beef appetizer, and the Deviled Eggs. So that is exactly what we did! It was very trusting, but we were blown away. The Wagyu Beef was one of the best things I have ever tasted and was the perfect yet generous portion of 4 oz. for the two of us hopping around, especially for the $22 price tag. They bring the experience to you with a 700 degree salted black lava cooking stone to prepare yourself. If that’s not convincing enough, it also happens to be a sustainable appetizer that allows them to “use the full resource provided”…or less glamorously stated, the trimmings. Even better! The deviled eggs were no ordinary deviled eggs. They were free range eggs with candied bacon, pickled root vegetables, gastrique, and truffle oil. Heavenly! Lastly, the mule was homemade and perfected with their long time in the works housemade ginger beer on tap.

Hey there, cutie 😉 – the restaurant on the left and bar on the right

Sweet Tooth, Always…

Jeni’s Splendid Ice Cream

First of all, if you’ve never tried Jeni’s ice cream, please RUN to your grocery store and pick some up! It’s become more widely available in recent years, so hopefully you can find it. My dad sold Jeni’s in his gourmet shop before it was ever carried in some groceries stores, so I’ve tried quite a few flavors. However, I hadn’t been to an actual Jeni’s Ice Cream shop, so we waited in the (luckily short at the time) line to try a new-to-me flavor, Gooey Butter Cake, in kiddie scoop size. The best treat after a day of walking around in the heat! Some of my favorite Jeni’s flavors include Brown Butter Almond Brittle, Churro, Frosé Sorbet, and Wildberry Lavender.


Since we were so pleased by the recommendation from the Basic Kitchen bartender to go Burwell’s, we took the Burwell’s bartenders recommendation to go to Carmella’s, an Italian cafe and dessert bar, nearby for dessert! We sat at the bar and ordered a glass of port and a s’mores ice cream sandwich on homemade brioche bread. To be honest, I think I ordered the wrong thing with the ice cream sandwich. It sounded better than it was. Somehow the brioche bread just didn’t work with the ice cream but on their own they were great. Apparently they have a cannoli cake, which is supposedly the best thing ever, but they didn’t serve it by the slice and I certainly was not about to order the whole cake! Nonetheless, we had fun chatting with our server behind the bar and this random girl who sat next to us. Oh, was she was a character!

Activities & Places To See in Charleston


South End Strolling

For a before or after dinner stroll, I recommend the waterfront park on the south end of the city near the popular Rainbow Row and Historic City Market (which is surprisingly air conditioned and has a Callie’s location!). It offers beautiful views of the Charleston harbor, old-fashioned park benches, a lawn for picnics, and wide walkways. The pineapple fountain was a popular photo spot, too!


I know I said we didn’t make any restaurant reservations, but we did book one activity in advance — a candle making workshop! We love to light candles in our apartment and go shopping for candles, but sometimes it’s hard to find scents that are just right. So, we made our own and officially became Chandlers! The workshop is in a private section in the back corner of the CandleFish store on King Street and also happens to be BYOB. Our class had 6 other people (I think they accept up to 10-12?), and yes, Spencer was the only guy. But it was totally comfortable and not weird at all. Anyway, the Chandler from the store takes you through the whole candle-making process from measuring the wax to pouring the candle, educating you on their history (they make Rewined candles!) and tips for making the most of your candles along the way.

You get to smell (blindly unless you turn it around to see the description) about 25-30 candles and mark your favorites and/or least favorites on the card pictured below. All of their candles are numbered and have no organization to them like you’d expect. You pick your favorite, grab the oil, and get started on making not one but two candles! Spencer made the #37 candle with cinnamon, anise and amber, and I made the #30 candle with bergamot, lemon, ginger, and musk. SO GOOD!

Exploring Outside of Downtown Charleston

North Charleston

Edmund’s Oast Brewing Company

To my fellow South Floridians, this brewery gave me major Funky Buddha vibes (in a good way)! It’s located in a modern development called Pacific Box & Crate that’s very tucked away and will have you feeling like you made a wrong turn until you see a guy carrying a growler of beer in the parking lot. I loved their Bucket of Flowers witbier with rose buds and orange peel, and the food looked and sounded super good coming from an open kitchen!

High Wire Distilling

We had seen and been curious about this never-before-seen gin on the shelves of many bars in Charleston called Hat Trick. When we were walking up to Leon’s, we saw this tucked away distillery and figured we would check it out. Turns out, they make Hat Trick! High Wire has a line of small batch spirits using specialized ingredients. They give tours and have a small bar where they can only serve 1 cocktail a day. They also sell retail but up to 3 bottles a day. Strange laws!

Mount Pleasant & Sullivan’s Island

Sullivan’s Island/Fort Moultrie

About 15-20 minutes outside of Charleston is popular beach town, Sullivan’s Island. It was exactly as I expected and I loved it! We went after brunch so we didn’t stop anywhere for food or drinks, but we drove around the island and walked by the beach at Fort Moultrie, which has a beautiful view of the Arthur Ravenel Jr. Bridge and downtown Charleston. Apparently it’s a great sunset spot too!

Grace & Grit

For brunch one day, we drove to Mount Pleasant to check out the highly-rated Grace & Grit modern Southern restaurant. We were craving grits, a Southern favorite we hadn’t yet tried in Charleston, and this was clearly the place. We got a grit flight starter with peaches & cream, blueberry, brussel pesto, and pimento cheese grits. You know I love trying weird combinations! I was surprised how much I loved the peaches & cream one especially. We also split a she crab soup and special breakfast sandwich with fried green tomato, ham, cheese, southern chow chow, and smoked gouda sauce. Amazing! The service and atmosphere were great too. If you wanted a boozy brunch, they also have mimosa flights.

Other Places To Consider in Charleston

See why I can’t wait to go back? So many more places to explore!

86 Cannon

Since you made it this far, I thought I’d share the trip highlights. I loved becoming a Chandler at Candlefish, the Wagyu beef at Burwell’s, the biscuit sandwich at Callie’s, the oysters at The Ordinary, and the cocktails at Felix Cocktails et Cuisine. Enjoy your trip!

In This Adventure

  • Bars

    • The Cocktail Club thecocktailclubcharleston.com

      Stylish speakeasy-style bar serving craft cocktails, plus a rooftop terrace.

    • Citrus Club thedewberrycharleston.com/drinks-dining

      The crown jewel in a city known for its steepled skyline and sea-skimming views, The Dewberry’s 8th floor terrace features the highest rooftop in Charleston. Home to our whimsical rooftop lounge, Citrus Club, features citrus-inspired cocktails, and fresh lite bites.

    • The Gin Joint theginjoint.com

      Cozy, intimate bar/eatery serving cocktails & eclectic small plates in a 1920s-inspired setting.

    • Edmund’s Oast Brewing Company edmundsoast.com

      Avant-garde beers, wood-fired pizzas & high-concept bar eats in a trendy, spacious locale.

  • Restaurants

    • The Macintosh themacintoshcharleston.com

      Creative menu items include bone marrow bread pudding at this lively farm-to-table American eatery.

    • The Ordinary eattheordinary.com

      This 1920s bank now houses an upscale seafood restaurant with high ceilings, large windows & a bar.

    • The Darling Oyster Bar thedarling.com

      Stylish spot with vintage appeal for creative seafood dishes, fry baskets & raw oysters.

    • Burwell’s Stone Fire Grill burwellscharleston.com

      Refined American & steakhouse fare offered in elegant, contemporary accommodations.

    • Felix Cocktails et Cuisine felixchs.com

      Seafood & steak sharing plates inspired by Paris, plus versatile cocktails & wines by the glass.

    • Basic Kitchen basickitchen.com

      Serene, light-filled space serving seasonal grain & veggie bowls, sandwiches & breakfast selections.

    • The Rarebit therarebit.com

      Bustling eatery crafting American comfort classics, from patty melts to chicken & waffles.

    • Leon’s Oyster Shop leonsoystershop.com

      Relaxed joint serving oysters, Southern-style seafood & fried chicken in a rustic, trendy setting.

    • Husk huskrestaurant.com/home

      An ever-changing menu of locally sourced Southern dishes served in a restored Victorian-era home.

    • Poogan’s Porch poogansporch.com

      Traditional Southern cooking served in a Victorian townhouse with porches & a massive wine cellar.

    • Grace & Grit gracegrit.com

      Creatively flavored grits accompany the surf 'n' turf at this area-sourced Southern specialist.

  • Cafes and Coffee Shops

    • Kudu Coffee & Craft Beer kuducoffeeandcraftbeer.com

      Hip coffeehouse with a courtyard patio also serves craft beers & hosts live music on the weekends.

  • Bakeries and Sweets

    • Callie’s Hot Little Biscuit calliesbiscuits.com

      Snug counter serve featuring several types of biscuits, plus grab-&-go sandwiches, coffee & tea.

    • Jeni’s Splendid Ice Cream jenis.com/scoop-shops/jenis-king-street

      Chain scooping creative flavors of ice cream & frozen yogurt made from local ingredients.

    • Carmella’s carmellasdessertbar.com

      Tranquil eatery featuring sandwiches & charcuterie, classic Italian desserts, wine & cocktails.

  • Distilleries

    • High Wire Distilling highwiredistilling.squarespace.com

      Located in the heart of historic downtown Charleston, SC, High Wire is dedicated to making premium, handcrafted, small batch spirits. Our approach is simple:  seek the finest ingredients available and develop recipes using a creative, culinary approach. 

  • Parks

    • Fort Moultrie nps.gov/fosu/learn/historyculture/fort_moultrie.htm

      Fort Moultrie is a series of fortifications on Sullivan's Island, South Carolina, built to protect the city of Charleston, South Carolina. The first fort, formerly named Fort Sullivan, built of palmetto logs, inspired the flag and nickname of South Carolina, as "The Palmetto State".

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