How to Spend Two Days in Charleston, South Carolina

If you’re looking for some southern charm, trade in your iced coffee for a glass of sweet tea in the oldest and largest city in South Carolina: Charleston! Pastel rowhouses, horse-drawn carriages, enchanting architecture, and history as deep at the Atlantic Ocean it sits beside. And of course, the amazing cuisine – from fresh seafood to soul food done right.

I’ve actually visited Charleston a TON – the entire side of my mom’s family is from James Island across the bridge. But, aside from spending hot summer days at grandma’s house or starry nights at family oyster boils, I never actually visited the city as a real “tourist” until now. It was a unique and memorable experience to explore the city with a new set of eyes as I brought my boyfriend in for the very first time. The adventures and memories these few days had in store were so much fun! So without further ado, here’s How to Spend Two Days in Charleston, South Carolina.

Day 1

Brunch at Millers All Day

Brunch is one of my favorite meals of the day, so we always make a mission to find a good place to eat a mid-morning meal when we visit a new town. Millers All Day is a colorful mid-century style restaurant on Lower King Street, known for its biscuits, boozy cocktails, and hearty bowls of grits. We started the day with waffles, a signature fried chicken biscuit, home fries, bacon, and an Apple Cider Mimosa – all very tasty! Although the popular eatery usually has a wait on weekends, it’s well worth putting your name on the list and standing by.

Browse the Shops on King Street

King Street has been named one of the best shopping streets in the USA several times – and for good reason! The thoroughfare is home to several boutiques, century-old family businesses, and widely recognized names. With a remarkable mix of antiques, art, fashion, décor, food, and more, it’s one of the most distinctive areas in Downtown. The street is divided into three sections: Lower King (Antiques District), Middle King (Fashion District) and Upper King (Design District). Spend some time popping into locally owned businesses and sampling foods, desserts, and drinks at nearby eateries.

Stroll The Battery

Known for its beautiful waterfront and antebellum-style homes, The Battery is one of the most popular places downtown for walking, biking, and enjoying scenic views. You might wonder, “why is there a seawall on the entirety of the city’s lower peninsula?” There’s a story for that! As indicated by its name, The Battery was a defensive fortification for the civil war to avoid invasion by Union troops. The seawall had cannons and weapons stationed there – although they were never officially used. Today, you can find memorials, cannons, and statues in the park that tell the story as well.

Support Local Makers at Charleston City Market

Shop-a-holics, this one’s for you! Located in the heart of Charleston, the Charleston City Market is home to over 300+ local vendors and artisans selling everything from candles to spices to fine art. The treasure trove of goodies is one of America’s oldest public markets, having opened in 1807. It’s definitely worth stopping by to meander through the nearly four blocks of open-air stands. For an authentic souvenir, spot out the sweetgreen baskets, handwoven with locally-harvested palmetto leaves. The works of art are a tradition of the local West African Gullah communities and have been passed down for over 300 years. If you typically collect something special when you travel, you’ll find it here (it’s magnets for me)!

Snag a Photo Op at Rainbow Row

While heading down East Bay Street, you’ll come across a row of 13 pastel-colored rowhouses lovingly referred to as Rainbow Row. It’s one of the most photographed areas of downtown, where you’ll see everything from engagement sessions to senior portraits. What’s interesting about this stretch of homes is that it wasn’t always what it is today. In fact, it became so rundown during after the Civil War that it was considered a slum. In the early 1930s, a woman named Dorothy Porcher Legge invested in a section of the homes and began to paint them pastel colors. Over time, other people purchased the surrounding homes and followed suit.

There’s a lot of debate on why the homes were painted in pastel colors. Some people think it was to capture attention for drunk sailors needing to find their way home. Some think it was for merchants advertising their items through color. Regardless of the reason, one thing’s for certain – you won’t want to to forget to snap pics here!

Take a Carriage Ride

Be swept away fairytale style on a leisurely horse-drawn carriage ride around Downtown Charleston. Taking one of the city’s carriages is a fun and era-appropriate way to step back in time, while immersing yourself in history. You’ll encounter colorful homes, churches, and some of the oldest surviving buildings in America along the way. While there are several carriage operators downtown, Palmetto Carriage Works is one of the top rated. It’s the oldest in town, and continues to be family owned and operated even today. Tours run between $35 and $45 per person, depending on time of day.

Dinner at Charleston Crab House

I’m a sucker for fresh seafood, so when I walked by the outdoor menu posted for Charleston Crab House, I immediately knew we were coming back for dinner. I am SO GLAD we did! The family-owned and operated restaurant has been serving up good eats for over 27 years, and it shows. We visited the Market Street location right across from the Charleston City Market – and boy was it delicious. To start, don’t miss the seafood-packed Bacon Wrapped Stuffed Shrimp, which comes with a side of red rice. For an entrée, I ordered the Grilled Seafood Trio with snapper, scallops, shrimp and garlic butter and Manny did the Grilled Atlantic Salmon. For dessert, the Reese’s Peanut Butter Pie was the perfect way to end the meal. Not only was the food cooked to perfect, but our server was so attentive and on-point. Do not miss this one!

Live Music, Drinks, & Dancing at Henry’s On The Market

Established in 1932, Henry’s is the oldest continuous restaurant in Charleston AND the state of South Carolina. The eclectic restaurant and bar features three levels and has live music every single night. Aside from the main level, there’s a rooftop bar and basement speakeasy that also feature stages for performances. On certain nights, they’ll even have different bands on all three levels. We headed there after dinner for drinks and music, and had a blast! The musicians were very talented and had a wide array of songs – from The Fugees’ Killing Me Softly to I Want You Back by The Jackson 5.

Day 2

Brunch at Port of Call Food Hall

Port of Call Food Hall is home to five locally-operated restaurants: a traditional oyster bar, an Asian fusion kitchen, barbecue, Greek food, and poke bowl spot. Aside from the food, it also hosts three full service bars each with 12 locals beers on tap. Since we were headed out for a busy day, this was a quick stop for sandwiches. But, the Nashville Hot Chicken from Palmira BBQ and the Banh Mi from Bok Choy Boy were so good, I didn’t get a photo. And THAT is saying something!

Visit Fort Sumter

One of the most historic sites in Charleston is Fort Sumter. The attack this man made “sea fort” marked the official beginning of the American Civil War in 1861. Travel back in time and learn about the military history of the island while appreciating stunning views of Downtown. Just be sure to prepare for lots of walking – wear comfy shoes! The only way to access the island is to purchase tickets for the National Park-approved tour boat, which departs from the Fort Sumter Education Center or Fort Moultrie.

Get Into the Spirits at Firefly Distillery

Two of my favorite things? Supporting local businesses and drinking delicious bourbon! Lucky for us, Firefly Distillery marries the two at an expansive tasting room and lawn in North Charleston. The family-owned and operated business holds the titles of Charleston’s oldest working distillery, and the creator of the world’s very first Sweet Tea Vodka. Indulge in six different Firefly spirits on their $10 Tasting Experience, where you’ll get to choose which samples you’ll try. Don’t miss out on their Southern Lemonade Vodka and the Bourbon Ball!

After the tasting experience, explore their History Room, learn about the history of Firefly Spirits, check out the Stillhouse where the spirits are distilled, and have a look into the production area and bottling line.

Have a Movie Moment at Cypress Gardens

Just 30 minutes outside of North Charleston, Cypress Gardens is a magical escape from the hustle and bustle city. It’s worth the day trip! The 175-acre swamp garden is a tranquil nature preserve where cypress trees tower overhead. Movie-lovers out there, you might recognize the park from the iconic swan scene in The Notebook! While Allie & Noah were surrounded by swans for the Hollywood magic of the film, in reality you can expect instead to encounter turtles, snakes, and alligators (oh my!). Don’t be scared though! We saw a 7-footer and a baby alligator on our row and both kept their distance without a hitch.

Entrance to Cypress Islands is only $10 with access to the boat rental, trails, Butterfly House, and “Swamparium” aquarium. Even though it’s just outside of Charleston, this budget-friendly beauty feels a world away.

Dinner at Amen Street Fish & Raw Bar

Located in the heart of historic downtown, Amen Street Fish & Raw Bar is a seafood staple with a full menu of delicious favorites! What first drew our eye to the restaurant was the stunning décor. The exposed brick walls, dark wood, and high ceilings evoked a certain warmth that felt inviting. After peering at the menu, it was a no-brainer that we had to sit down. The Amen Street Shrimp Roll was fresh and light, with lemon aioli and chives adding a certain brightness to it. The Amen Burger, though simple, was cooked to perfection. And the Owner’s Famous Frozen Peach Bellini was a refreshing marriage of peach Schnapps, puree, rum, and champagne.

Statement on Charleston and the Trans-Atlantic Slave Trade

For us, this trip was mostly about food, relaxation, and mindless fun. There’s a lot of history in Charleston, much of which can be both interesting and painful to encounter. The trans-Atlantic Slave Trade was one of the largest industries in historic Charleston. In fact, Over 40% of all enslaved Africans who came to North America arrived through Charleston Harbor. This was something that I personally did not want to encounter in my spirit on our trip – imagining my ancestors, and my family, going through all of the things they did. However I would be remiss if I did not name the sites that display these painful truths for informational purposes. If you are in the emotional space to revisit this history, here are some of the “must-sees” on the list.

  • The Old Slave Mart Museum, located at 6 Chalmers Street, tells the story of Charleston’s role in the domestic inter-state slave trade from 1856 to 1863.
  • Magnolia Plantation and Gardens has been recognized as one of America’s most beautiful gardens. They offer tours at this historical site, including the Audubon Swamp, nature boat cruise, tram ride around the nature preserves and an award-winning “Slavery to Freedom” presentation in African-American history.
  • Drayton Hall is located on the Ashley River in North Charleston, and is the only plantation to have survived both the revolutionary and civil wars on the river.

As you can see, Charleston is a vibrant city with rich history, amazing Lowcountry cuisine, and beautiful architecture. On your visit, you’ll encounter Southern charm and hospitality that’ll make you never want to leave. Have a wonderful trip, and be sure to share your adventures with me!

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