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  >  Destinations  >  United States  >  Exploring Charleston: Four day weekend from New York City

Charleston Overview

Charleston beautifully blends old-world charm with modern attractions. Wander through cobblestone streets lined with historic churches and exquisite Antebellum houses. Experience the allure of horse-drawn carriages clip-clopping through the historic district. Discover the many rooftop bars and indulge in the many wonderful restaurants that bring together Southern and international flavours. Immerse yourself in American history with visits to nearby plantations and unwind by the Water at Folly Beach and Shem Creek.

We spent four days in Charleston, the perfect amount of time to explore the city and take in the sights and culture.

Uncover Historic Charleston

Charleston is easily explored by foot. We spent a lot of time walking around the downtown over several days. We spent time window shopping along King street. We wandered through the Old Slave Mart, and we also explored Rainbow Row and the nearby surroundings. Rainbow Row is the longest stretch of Georgian row houses in the US, boasting captivating pastel colors reminiscent of the Caribbean. While it is the famous stretch, we found the houses on Church Street and the Battery promenade to be more of a sight. Church street is filled with elegant brick homes many with picturesque courtyards. And the Battery promenade is lined with Antebellum-style mansions that are certainly worth viewing. Plus, while walking along, you’ll see Fort Sumter in the distance, which is where the first shots of the Civil War resounded. We also walked through the main part of town checking out many bars and restaurants as well as the historic Charleston market.

Historic Charleston

Charleston’s Culinary Scene

With its seafood shacks, rooftop bars and a dizzying array of “must-try” restaurants, Charleston is a foodie’s paradise. Many menus are built around Lowcountry dishes, but offer a creative interpretations of the old favorites. Beyond shrimp and grits, regional fare included oysters, pimento cheese, fried green tomatoes, she-crab soup, and fried catfish. We tried to fit in as many amazing restaurants as possible. Full list can be found on this google map. Highlights include the tilefish and s’mores ice cream at Husk, sitting in the courtyard at South Bound sipping cocktails and the salted caramel chocolate chunk ice cream at Kilwins.

Dinner at South Bound

Magnolia Plantation: A Historic Tour

I was initially not very interested in going to tour one of the many plantations around Charleston. But my friends were and after a bit of research, it seemed like the gardens at Magnolia would be worth a visit. As it turns out, I found the tour and learning about the history super informative and well worth the time to understand the plantation’s history.

Magnolia was founded in 1676 by Thomas and Ann Drayton and 15 generations later, the Drayton family still own the plantation. We started our visit by doing the nature tour, which is a nice way to see the property and tour the plantation grounds including seeing the alligators! But the highlight was the Freedom to Slavery tour, which showcased the four former slave cabins that are preserved on the property. The tour guide did an excellent job explaining the history of Magnolia and bringing to life the hardship that the thousands of enslaved families that lived and worked on the property would have experienced.

Picture a small cabin which is just basically a shell, where a family of 12-18 would have lived. They would spend all day working in the rice fields under extreme heat and in infested waters, making for a short lifespan. After Emancipation, roughly half of the newly freed workers decided to stay at Magnolia. In fact, there are still some there working on gardeners.

It’s a difficult story to listen to but an important part of our history and the team there do a great job of bringing it to life.

Magnolia Plantation

Boating in Charleston

Flanked by creeks, marshes, rivers and the Atlantic, Charleston is an ideal place to kayak, swim, boat or paddle board. We visited Folly Beach for drinks and took in the beachy vibe. We booked a private boat tour around Folly, which got us out on the water for sunset. We brought a picnic with us and enjoyed champagne & sandwiches for dinner while taking in the coastal view. We also searched for dolphins and found plenty of them!

Separately, we also visited Shem Creek. We did not end up kayaking or paddle boarding as it was really hot, but we did have lunch and some frozens at one of the restaurants along the creek.

Charleston Battery
Boat ride Charleston South Carolina

Swimming in Charleston

Given we were staying in an Air BnB, we didn’t have access to a pool and it was hot! We spent one afternoon renting a cabana at the Mills Hotel Pool, which was a lovely spot to plant ourselves in the mid-afternoon heat. The hotel is centrally located so it was perfect for swimming and hanging out, but also leaving to go walk around and grab lunch in the historic downtown. We also visited the MLK public pool, which was also a refreshing dip after a day in the sun. It’s a huge public pool and has a retractable roof so it is perfect for all weather conditions.


Charleston is such a perfect destination for a four day weekend. There is so much to do in the charming city itself, and the nearby areas are also wonderful. Between the plantations filled with history, the beaches and inlets for water activities, and the culinary scene, four days will be jam-packed with fun. Check out the tips & recommendations for specific suggestions on what to do and where to go in Charleston.

Couple at Magnolia Plantation