Southern Charm: A Historic Itinerary for Charleston, South Carolina

Magnolia Plantation

This year’s wedding anniversary trip for my husband and I was to Charleston, South Carolina: a place that has been on our radar since we were considering a visit when travel restrictions were beginning to lift during COVID. Grad school steered us in a different direction that year, and I think we ended up doing a long weekend in New York City.

We picked Charleston this year since we were looking for a direct flight under 3 hours from home, walkable, and accommodated about 4 full days worth of activities without completely packing the itinerary from sunrise to sunset. The food scene is incredible! We didn’t have a single bad meal. Eat anywhere and try as many places as you can! Weekend nightlife in Charleston is one to write home about, so make sure you bring a fit worthy of a Friday or Saturday night on King Street. We visited Charleston during the Juneteenth holiday and I cannot recommend this time enough to fully experience the potency of the stories these lands hold.

Something I learned about myself in good humor: coming from Newport, Rhode Island, I have a very different definition of the term “walkable” than others may have. Charleston itself is rather large. The historical plantations are about 20-30min outside of town, there is limited parking in the city, and a lot of ground to cover on foot. My husband and I didn’t rent a car, and our itinerary was a little all over the place (not my best planning work) – so we wound up scheduling a few more rideshares than necessary.

My itinerary below is how you can maximize your visit using rideshare such as Uber or Lyft. If you do decide to rent a car so you can drive to the plantations yourself, I’d still recommend walking or taking a rideshare into the heart of Charleston because parking is so limited.

“Perhaps travel cannot prevent bigotry, but by demonstrating that all peoples cry, laugh, eat, worry, and die, it can introduce the idea that if we try and understand each other, we may even become friends.”

~Maya Angelou

Day 1 – Explore the town, historical landmarks and the Battery

Hitch a Lyft to the middle of the French Quarter to the Charleston City Market, open daily since 1807. Here you’ll find blocks of all sorts of artisans, snacks and wares (oh and public restrooms). Start at the northern end and work your way towards the water. Walk along the Battery until you reach the Pineapple Fountain. I’m still not entirely sure why it is deemed a must visit on Trip Advisor, but I’ve decided it’s because it looks cool and you’re welcome to wade in. My husband and I certainly did after doing all that walking in the 90 degree June humidity. After the fountain, head towards the Slave Market Memorial and Old Exchange and Dungeon. You can take a tour inside the Old Exchange and Dungeon if you wish. After that, walk to Rainbow Row, 13 houses built in the 1700s. I’ve got to say, it must be some time since whatever images have been posted on the internet because the trees in front of those colored houses have grown. A lot. It’s still a great spot for pictures, but you’re going to need to get creative. I’ll leave you to it.

Day 2 – Fort Sumter and the African American History Museum

Fort Sumter is only accessible by ferry with three self-guided tours per day. Tours are offered from both Liberty and Patriot Parks with a 30min ferry ride each way and 1hr at the Fort to explore and walk through the museum. If you take the morning or afternoon tour, you’re able to assist with raising and lowering the flag of the 33 colonies. Don’t forget to keep an eye out for dolphins in the bay!

Before or after your tour to Fort Sumter, visit the African American History Museum on the neighboring pier. This is (and I cannot emphasize this enough) a MUST during your visit to Charleston.

Day 3 – Boone Hall and the USS Yorktown at Patriot Park

Continue growing your knowledge of the Gullageechie culture and the history of plantations in the south by visiting Boone Hall, one of the oldest and longest running plantations in operation. Plan to spend at least 3hrs here.

After exploring the hall, head down to Patriot Park and hop aboard the USS Yorktown, an aircraft carrier with an impressive history and collection of 21 historic aircraft. Patriots Park and the USS Yorktown offer several different tours that cater to your military history interests, so definitely check their website. We opted for the Ghost Tour of the carrier – less because we thought we would encounter the supernatural – but more because we thought being on the ship at night would be both cool and creepy. We took a 7:30 tour that landed us on the flight deck for sunset.

Day 4 – Magnolia Plantation and Gardens and Drayton Plantation

Take a ride share about 25min outside downtown Charleston and out to the neighboring plantations, Magnolia and Drayton. The gardens at Magnolia are extensive, however walkable, and contain a wildlife sanctuary, bridges, turtles, birds and alligators. While we were there, there was an art installation, Lego Pop, a series of animals sculpted from Legos placed throughout the grounds. While a house tour is a separate ticket, access to all gardens, a guided ride of the grounds and the Slavery to Freedom tour are included in general admission. Plan to spend several hours here before going a short 5min down the road to Drayton Hall. Built in 1738, it’s the oldest, unrestored plantation house in America open to the public. Admission grants a 1hr guided house tour and access to the grounds, gardens, African American Cemetery, conservation laboratory and Caretaker’s House.