5 activities for your first trip to Charleston, South Carolina

5 activities for your first trip to Charleston, South Carolina

Charleston, South Carolina, was a bucket list item of mine for many years (we did not quite make it there on our original epic road trip through the South). I know so many people who count it as one of their favorite cities. And whenever I mention how much I love Savannah, Georgia, Charleston inevitably comes up. This year I finally made it to Charleston and let me tell you, this Southern gem did not leave me disappointed. If you are a first-time visitor like me, I highly recommend the following five activities for your first trip to Charleston.

Poogan’s Porch

Enjoy brunch at Poogan’s Porch, especially if you like beautifully restored Victorian houses. Established in 1976, they serve delicious, Lowcountry cuisine. The homemade buttermilk biscuits are the best I have ever had. Note: they are only open for brunch and dinner and you may need a reservation.

Poogan's Porch sign, a must for your first trip to Charleston, South Carolina
Brunch at Poogan’s Porch is a must.

Two Sisters Walking Tour

I honestly cannot recommend Two Sisters Tours enough. It was the best walking tour I have been on in my life. Mary Helen and Therese are the sisters behind the company. Raised in downtown Charleston, the two can trace their family roots in this city back to 1793. Mary Helen was our tour guide and she was an absolute delight. She was also wicked smart and shared so many historical and personal stories about Charleston. I never wanted the tour to end.

Two Sisters Tour guide for a first trip to Charleston, South Carolina
Our fearless guide.

Explore (more) on foot

Charleston is very walkable and there is so much to see and learn. Since being founded in 1670 (as Charles Town), this city has experienced its fair share of American history, including the Revolutionary War, slavery, the Civil War, hurricanes and a restoration. We learned a lot on our walking tour, but there is still a lot to see in Charleston.

Do not miss:

  • Saint Michael’s Church is the oldest surviving religious structure in Charleston.
  • Four Corners of Law refers to the intersection of Meeting and Broad Streets, where the buildings occupying the four corners include St. Michael’s Church, Charleston City Hall, Charleston County Courthouse and the United States Post Office and Federal Courthouse. Federal, state, local and ecclesiastical law are all represented…in beautifully constructed, old buildings.
  • Charleston was originally a walled city. You can see the remains of that wall at East Bay and Cumberland.
  • The cobblestone streets in Charleston are unique and make excellent photos. Chalmers Street in the French Quarter is a popular street to take those photos. However, there are eight cobblestone streets around the city. The stones came from Europe in ships that used them as weights when there was not enough cargo.
  • The architecture in Charleston is worth the trip alone. The pastels houses on Rainbow Row make it a tourist destination, but there are so many wonderful homes throughout the city. Each angle and view is photo worthy. I particularly enjoyed seeing the different architecture trends represented by each district.
  • The Battery is a must. This landmark defensive seawall and promenade is both historic and beautiful.
  • Dock Street Theatre is located in the historic French Quarter, which also deserves a visit.
Charleston street with pastel houses
Just a typical view in Charleston. This city is lovely to walk around and explore.

I am sure there are other sites worth visiting, but we only had limited time to explore. I will just have to go back and walk around Charleston some more!


All the walking around Charleston made us hungry! So we headed to a joint called Henry’s, a restaurant, bar and nightclub that was established in 1932. That makes Henry’s the oldest continuous restaurant in Charleston and the state of South Carolina. The place is eclectic and centrally located. The food is Southern and delicious. I went for the fried chicken and C went for the shrimp and grits. Neither of us left disappointed.

Fried chicken lunch at Henrys in Charleston, South Carolina
Tasty Southern fare.

Charleston City Market

If you are looking for souvenirs, head to the Charleston City Market. You definitely want to head here to see and purchase sweetgrass baskets. They are works of art. However, be prepared to spend a pretty penny since these baskets are not cheap (understandably since they take so much time and effort to make). I was not sure what I would do with a basket when I got it home, so instead I purchased a pair of sweetgrass earrings as a souvenir.

sweetgrass basket making in Charleston, South Carolina
Amazing sweetgrass baskets.

There are plenty of other goods to spend your money on as well (like handcrafted bath and body products from the Old Whaling Company). Just keep your eyes peeled for the “Certified Authentic Handmade in Charleston” seal. A product with that seal is 100% locally made.

It is no secret that I have a bit of a shoe problem. So when Mary Helen told us that her shoes were from a local company called the Charleston Shoe Co., I knew I had to check them out. The shoes are unique and fairly affordable. Mary Helen assured us they are very comfortable and she did not appear to have any issues walking around on Charleston’s cobblestone streets. So I picked up a pair of brightly colored sandals. Now I just have to wait until summer to really wear them.

five activities for first trip to Charleston
Cobblestone streets, the old wall, shoes from the Charleston Shoe Co. and Mary Helen–all my favorite things from Charleston (minus the Southern food)!

Other Charleston activities:

I cannot vouch for a tour of Fort Sumter, a haunted walking tour or a ride in a horse-drawn carriage since I did not experience them personally. But I did have some locals recommend them, so they might be worth checking out.


If you have not been to Charleston, South Carolina, I highly recommend you get on that. Be sure to sign up for a walking tour with Two Sisters Tours and try out the five activities for your first trip to Charleston recommended above. You will not leave disappointed.

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