Charleston Weekend Getaway: Perfect Itinerary

Charleston weekend trip itinerary: Day 1 

On your first day in Charleston for the weekend, I recommend you grab a big breakfast and then spend the bulk of your day at two significant historical sites: Aiken-Rhett House and Fort Sumter National Monument. 

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Aiken Rhett house 

Aiken-Rhett House was once the home of Governor and Mrs. William Aiken Jr.

William Aiken Jr. was the 61st governor of South Carolina, from 1864 to 1866. While Nathaniel Russell House (nearer The Battery in lower Charleston) has been beautifully restored, if you’re looking for a historic Charleston home that’s been carefully preserved, I recommend you tour Aiken-Rhett House. 

Aiken-Rhett House has been called “the most intact townhouse complex showcasing urban life in antebellum Charleston” by the National Trust for Historic Preservation. 

While the main house is quite a sight, you also won’t want to miss the carefully preserved quarters in the back of the house where many enslaved people (including children) lived and died to maintain the Aiken-Rhett “way of life.” 

Aiken-Rhett House is managed by the Historic Charleston Foundation, which also looks after Nathaniel Russell House. 

To get the most out of your visit to Aiken-Rhett, download the free Historic Charleston Foundation app onto your iPhone so you can listen to the audio tour. 

Fort Sumter 

Fort Sumter is probably best known as the starting place of the American Civil War when it was fired upon by Confederate forces on April 12, 1861. 

Fort Sumter sits on a man-made island in Charleston Harbor and is only accessible by boat. You’ll want to book your tickets ahead of time online through Fort Sumter Tours, the National Park Service’s official vendor. 

Plan to arrive at the Visitor Center at least 30 minutes before the ferry leaves.

There are restrooms available in the Visitor Center. And a gift shop! There’s also a gift shop at the fort, but don’t wait too long to stop in because it may close before the end of your visit if you’re in the last tour group of the day. 

Inside the fort, don’t miss the history talk from the National Park Service ranger. I thought it was really well done and provided some important historical context. 

The ferry ride to and from the fort can be rather breezy. Even though it was a very warm day, I was glad I brought a jacket along. You can also choose to take the ferry to Fort Sumter from Patriots Point in Mount Pleasant. 

Charleston getaway itinerary: Day 2 

Stroll along The Battery 

Parking: Look for street parking near the water, which will be easier to find early in the morning if you can. 

Start day two of your Charleston weekend trip down at The Battery. It’s called The Battery because there was a coastal defense artillery battery there at one time. 

You’ll find The Battery along the lower Charleston peninsula. The seawall promenade here makes a nice place to walk. I think that the lovely White Point Garden adjacent is also a nice place to take a stroll or enjoy some shade on a hot day.

Some really beautiful homes around the battery show off the stunning Charleston architecture. Have fun walking around and enjoying your beautiful surroundings. 

Visit the historic Charleston City Market 

The four-city-block-long Charleston City Market is considered by many to be a “must-do” in Charleston. 

The market is full of fun stalls to look through. You’ll find beautiful art and decorative works from local artisans as well as traditional items like sweetgrass baskets that have been made in Charleston for centuries. 

It’s a wonderful place to explore and find some great souvenirs to take away with you to remember your visit to Charleston. 

Waterfront Park 

This beautiful stretch of waterfront is where you’ll find Charleston’s iconic Pineapple Fountain, a top photo spot in the city. 

This is an ideal place to slow down for a few minutes and just enjoy being in Charleston. It’s also conveniently located near Fleet Landing, one of our top food picks in Charleston. 

If you have time, take a few minutes to walk out on the pier for great views of the harbor and the Arthur Ravenel Jr. Bridge. There are some nice bench swings out there if you’re looking for a nice place to sit down and catch a nice breeze on a warm day. 

Unpopular opinion: Rainbow Row is overhyped   

About a six-minute walk from the Pineapple Fountain in Waterfront Park, you’ll find a row of houses on East Bay Street in Charleston known as “Rainbow Row” because the houses have been painted in bright and pastel colors. 

It’s a popular spot, particularly with Instagrammers. If you want to see it, then by all means you should take a few minutes out of your day to do it.  I found it overhyped and underwhelming. 

Enjoy dessert and coffee at Carmella’s Dessert Bar  

When you’re ready for some dessert or coffee, or if you just need a break during your trip to Charleston, I highly recommend stopping in at Carmella’s.  The café is beautiful, the coffee and gelatos are excellent, and they have a variety of other desserts to choose from.  

And their beautiful cakes are large enough to share…or get it to go and keep it to yourself in your hotel room. I’m just saying.  Carmella’s also offers a variety of sandwiches if you’re looking for a quick bite. 

Other great things to do during your Charleston weekend getaway, if you have time

Here are a few more ideas for things you could add to your Charleston vacation and get to know this Southern city better.

Old Slave Mart Museum

The Old Slave Mart Museum in downtown Charleston shines a light on the city’s past role in the domestic inter-state slave trade from 1856 to 1863. The museum is housed in probably the only known building that was once used as a slave mart that is still in existence.

The Old Slave Mart Museum is an important part of American history, and it provides visitors with important information on the most painful parts of American history. If you have time in your Charleston itinerary, visit this museum in the historic district.

Old Exchange and Provost Dungeon

The Old Exchange and Provost Dungeon is a Charleston and national historic landmark. For the past 250 years, this historic building has been used as a commercial exchange, custom house, post office, city hall, military headquarters, and museum.

The Provost Dungeon on the bottom floor was used as a prison during the American Revolution, and it contains exhibits that tell the story of this important period in U.S. history.

Where to stay in Charleston 

Where to eat in Charleston 

Our top pick for lunch in Charleston is Fleet Landing. Reservations are strongly recommended. If the weather is good, ask for a table outside if you can get one. Great food, good service. Highly recommend. Order the hush puppies. 

Fleet Landing also helpfully offers gluten-free and vegetarian menus. 

Hyman’s Seafood has developed a bit of a reputation as a tourist trap, but we think it’s still a fun place to eat. It’s family-owned, the food is good, and you just might have the chance to chat with the owner. They happily helped with Hubby’s dietary restrictions. 

We stayed at the Doubletree in Mount Pleasant outside Charleston and enjoyed some great local breakfast spots before heading into Charleston for sightseeing for the day. 

• Vicious Biscuit: amazing biscuits (including gluten-free biscuits!) and good coffee too. 
• Page’s Okra Grill: elevated classic diner fare (like steak and eggs, French toast, etc.).

When to visit Charleston 

Our recommendation is to enjoy a visit to Charleston, South Carolina, in either the spring or later in the fall. 

Summer can get unbearably hot. Aaaand…the hottest months in Charleston are typically also the wettest. So plan for rain. 

And while temperatures in the early to middle of fall can be more pleasant…it can also bring the possibility of hurricanes. So, keep that in mind. 

How to get around in Charleston 

If you’re staying in the historic center of Charleston (see our hotel recommendations above) or it’s not too hot, then walking is a great way to get around Charleston. 

However, you may find that some of the sites you want to see are farther apart than you prefer to walk. Try grouping sites and activities geographically when you can to minimize walking. 

Or if you want to drive, you can also minimize the number of parking garages you’ll be in and out of on your trip, saving you a little money.