Long weekends are the perfect opportunities for spontaneous road trips. While my mom went to visit my sister in New York over Memorial Day weekend, my dad and I hopped into the car with Paddington and headed to Charleston. After seeing endless photos of cute and colorful Southern houses and hearing about all of the must-visit restaurants and boutiques, I couldn’t wait to explore the city for myself.
Charleston is about a six-hour drive away and we arrived on Friday evening with time to check into our Airbnb and grab some dinner. We were surprised to find how much “character” our house had. Some of the house’s quirks were gorgeous, like the big windows and high ceilings, while others were less desirable, like the extremely slanted floor and awkward-sized bathroom. In the end, we overlooked the house’s eccentricities in favor of its great location. A short walk down the street took us to Le Farfalle for a late dinner where we had the most amazing rosemary focaccia, pork meatballs, handmade pastas, and Italian-inspired cocktails.
We started off the next morning with breakfast at Poogan’s Porch, a quiet house-turned-restaurant with the most charming front porch and back patio. I devoured the egg white omelet with artichoke hearts and goat cheese, and Dad loved the down home breakfast with baked spiced apples.
After breakfast, we picked up Paddington from our house and headed out to explore Charleston’s architecture. We walked down Tradd Street towards Rainbow Row and saw tons of cute houses in bright colors with painted shutters and blooming flower boxes. It was simply magical! It turned out to be a day of record-breaking heat in Charleston, so we ended our walk at Waterfront Park where we snagged a swing on the pier and let the sea breeze cool us down.
We had worked up an appetite for lunch and Lewis Barbecue was the perfect place to refuel. I haven’t had beef barbecue at all since moving to Birmingham, so I was so excited to order a few slices of brisket with sides of mac and cheese, potato salad, and baked beans. After lunch, Dad and I walked up and down Cannon Street and King Street to check out a few boutiques. Some of my favorites included stationery shop Mac & Murphy, men’s lifestyle shop Indigo & Cotton, and pretty PJ shop Lake Pajamas, but Candlefish was the one store that truly stole my heart. They have a “library” of 100+ candles that you can smell to find your signature scent. None of the candles have official names; so instead, the girls at the counter have a big notebook with all of the candles listed by number and scent. I got #33, which is masculine and musky with floral notes.
We wrapped up our day of exploration with old-fashioned burgers and Moscow mules at Little Jack’s Tavern. This place definitely has more of a bar vibe than restaurant vibe, but we enjoyed relaxing somewhere casual after being out and about all day. To satisfy our post-dinner sweet tooth, we got scoops of ice cream and warm waffle cones from Jeni’s. Dad loved the brambleberry crisp flavor, and the dairy-free dark chocolate flavor was the best dairy-free ice cream I’ve ever tasted!
The next morning, we tried to go to Callie’s Hot Little Biscuit for breakfast, but the line was so long before the shop even opened that we decided to get donuts from Glazed instead. We were blown away by how delicious and creative their flavors were! I got a peach cobbler donut and a peanut butter chocolate donut, and Dad got the purple goat (their best-selling flavor) and an apple fritter.
In order to work a little history into our trip, we headed over to the Aiken-Rhett House for a self-guided tour. The house was originally built in 1820 and is known as one of the most well preserved historic homes across the country. The property consists of a grand main house with gorgeous ballrooms and verandas, a rustic carriage house for the family’s horses and buggies, and unfathomable slave quarters that include multiple bedrooms and the kitchen and laundry facilities for the property.
I highly recommend using the audio tour app while walking through the house. We liked being able to move at our own pace, but the narrator shared so many interesting details that we wouldn’t have discovered by just looking at the house. One of my favorite parts was seeing layers upon layers of old paint and wallpaper on the walls.
For lunch, Dad and I went back to Callie’s Hot Little Biscuit for egg, bacon, and cheese biscuit sandwiches. There was no line at all during lunch hours, so I’m assuming the mad rush is only first thing in the morning with the breakfast crowd. It was well worth the wait though, because it was honestly the best biscuit I’ve ever eaten! What makes it so special? One word: BUTTER.
Our afternoon excursion was a boat tour of Charleston aboard the Schooner Pride. It was so nice to soak up the sun and sea breeze while seeing the city from a different point of view. The motorized sailboat has three large sails that the staff has to manually raise and lower. Once we got out to sea, they asked for volunteers to help raise the sails and Dad quickly raised his hand! When they gave the word, he pulled on the ropes and the sails flew to the top. He made it look effortless, but it definitely takes some muscle to accomplish. Our hour and a half trip took us out to Fort Sumter and back, and even included a few dolphin and jellyfish sightings!
The tour guides at the Aiken-Rhett House recommended we see the Nathanial-Russell House as well, so that was our next stop. While the Aiken-Rhett House was preserved, meaning it’s been pretty much untouched since the 1800s, the Nathanial-Russell House was beautifully restored, meaning it’s been renovated to look exactly like it did back in the 1800s. The walls are painted in bright, bold colors, and the rooms are filled with neoclassical furniture and personal belongings. Like the Aiken-Rhett House, the Nathanial-Russell House was home to a big, wealthy family with slave quarters on-site; however, instead of residing in a quaint and quiet neighborhood, the Nathanial-Russell House is located on Meeting Street, right in the middle of town.
From there, we walked down Rainbow Row to The Battery and White Point Garden. The Battery is a historic landmark for the defensive seawall that surrounds the tip of Charleston. While it was cool to see replicas of old cannons and walk around the tree-filled park, the experience overall was a little underwhelming.
We wrapped up our weekend trip with dinner at Leon’s Oyster Shop. This place was easily the most recommended restaurant to me, so we had pretty high expectations! After waiting for about 30 minutes for a table, we were seated and I ordered the fried shrimp basket, Brussels sprouts, a rosé slushie, and a tequila and grapefruit cocktail called Little Bird. Dad ordered Leon’s fish fry, which came with fried catfish, fried oysters, fried shrimp, cole slaw, and hush puppies. Everything was SO delicious and tasted quintessentially Charleston. We loved being able to soak up the soul of this historic Southern city in just a few activity-filled days.