The Holy City {Charleston, SC}
Southern Experiences

The Holy City {Charleston, SC}

Charleston, South Carolina is known for its bright colored streets, southern hospitality, and rich history. It is a city that needs to be on your bucket list. With something for everyone, Charleston provides the perfect backdrop for a weekend getaway. Below is a suggested itinerary for a long weekend.

The Holy City {Charleston, SC}

Need a place to stay? Check out Andrew Pickney Inn.


There is more to Charleston than just the city. With several plantations dotting the countryside around the city, start your weekend off by exploring the land of the people who influenced this city. As I mentioned, there are several to choose from, but my favorites are Boone Hall Plantation, with its avenue of oaks; Middleton Place, the oldest landscaped gardens in the country; or Magnolia Plantation & Gardens, America’s first public garden. All of these plantations will take a few hours to tour, so map it out in advance. Luckily, Middleton Place and Magnolia are neighbors.

Middleton Place | Charleston, SCMagnolia Plantation & Gardens | Charleston, SC

Exploring many plantations will take a good part of your day, but if you have time swing by Charleston’s famed Angel Oak. This Southern live oak is located in located in Angel Oak Park (clever!) on Johns Island. The tree is estimated to be 400 to 500 years old and produces shade that covers 17,200 square feet. At its highest point, it stands at 66.5 feet. It’s a place you’ll not want to miss! Please note – The park is open until 4:00 PM Monday to Saturday and until 5:00 on Sunday.

Angel Oak | Charleston, SC Angel Oak | Charleston, SC

Saturday Evening

Spend the evening strolling through Charleston’s City Market. Charleston’s historic City Market is the cultural heart of Charleston since 1807, and one you must visit. Stretching down four city blocks, City Market is a great place to meet some of Charleston’s local artists and is a great place to purchase souvenirs from your visit, like Sweetgrass Baskets. The Market is open daily from 9:30 AM to 6:00 PM and from 6:30 to 10:30 PM on Fridays and Saturdays during the months of April to December.

City Market | Charleston, SCCity Market | Charleston, SC

Once you’ve done a little shopping, stop for dinner at Henry’s House. I’ll save you the trouble – this restaurant has the best she-crab soup in the city!


If the weather is nice, spend today getting to know the birthplace of the American Civil War with a trip to Fort Sumter. You’ll definitely want to check out boat times in advance of arriving so you don’t have to spend too much time waiting. If you have kids, the aquarium is right next door!

Fort Sumter | Charleston, SC

Upon finishing your tour of Fort Sumter, head back downtown for lunch at Charleston Crab House. Spend the afternoon exploring Charleston! The city is easy to navigate for pedestrians.

Charleston, SC

The two items you’ll not want to miss are the Pineapple Fountain and Rainbow Row.

The Pineapple Fountain is one of the city’s symbols and is located in Waterfront Park. This area of the Charleston is perfect for a resting spot and to soak up the sea breeze.

Pineapple Fountain | Charleston, SC

Rainbow Row is the nickname of thirteen colorful Georgian row houses due to their bright facades. In fact, this is the longest stretch of Georgian row houses in the United States and is one of the most photographed spots in Charleston.

Rainbow Row | Charleston, SC

shirt (similar) // shorts // shoes // watch

Rainbow Row | Charleston, SC

Sunday  Evening

Before dinner, grab drinks on the rooftop of Market Pavilion Hotel. You do not have to be a guest to access the rooftop bar, and it offers splendid views of the city from above. Then head off to dinner and grab some pralines for dessert at Savannah’s Candy Kitchen.


Before you leave Charleston, you must take a carriage ride. This is a fun way to see different parts of the city and to learn a little more history. After your tour, if you have time, take yourself on a walking tour of Charleston’s old churches.

Charleston, SC Charleston, SC Charleston, SC Charleston, SC Charleston, SC Charleston, SC