See the Best of Charleston: A 3 to 5-Day Itinerary

Charleston is regularly ranked one of the top vacation destinations in the United States. If you’re planning a Charleston trip, you’ll find hundreds of three-day itineraries. But there’s so much to do in Charleston, you could easily spend more days. In this article, I’ve included five full days of plans, ranging from sightseeing to shopping to outdoor activities. You can choose any three itineraries—or all five—and still be confident you’re experiencing the best Charleston has to offer.

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Best Things to Do in Charleston

Day 1

Take a Carriage Tour

First, to get familiar with the city, book a carriage tour of the historic district. Popular tour companies include Palmetto Carriage Works, Old South Carriage Company, and Charleston Carriage Works. All three, located near East Bay Street, offer hour-long public or private tours.

We chose Palmetto Carriage Works because it offers free downtown parking all day Sundays through Thursdays. You can also get a $2 discount on tickets with a coupon from the Charleston Area Convention & Visitors Bureau. We enjoyed the leisurely ride through Charleston’s residential streets in an eight-person carriage pulled by a two-mule team. Notable landmarks on our tour included the Charleston City Market, the Cathedral of St. John the Baptist, and the allegedly haunted Old Charleston Jail. But note that every tour is different. The city of Charleston heavily regulates the carriage drivers, using a lottery system to assign each route.

Have Lunch at a Rooftop Bar or Restaurant

After your carriage tour, have lunch and drinks at one of Charleston’s many rooftop bars and restaurants. Options in the historic district include Eleve, Citrus Club, Pavilion Bar, Henry’s on the Market, and The Watch.

We tried The Rooftop Bar at The Vendue, a boutique hotel just a six-minute walk from Palmetto Carriage Works. The Rooftop Bar overlooks Charleston Harbor and Waterfront Park. Its menu includes light bites, sandwiches, and salad, and an array of local beers and specialty cocktails. Sample the Red Moon Margarita, which combines a spicy jalapeno-infused tequila with a sweet blood orange puree.

Visit a Museum or Historic House

If you’re a history lover, spend some time at one of the numerous museums and historic houses of the historic district. The Charleston Museum on Meeting Street is one of the oldest museums in the United States, founded in 1773. It also operates two historic homes, the Joseph Manigualt House and the Heyward-Washington House. Depending on how much time you have, you can select a museum-only ticket or opt for a two- or three-site ticket, including either or both houses.

Other notable museums and houses in downtown Charleston include the Old Slave Mart, the Old Exchange & Provost Dungeon, the Aiken-Rhett House, the Nathaniel Russell House, the Edmonston-Alston House, and the Williams Mansion (formerly known as the Calhoun Mansion).

Day 2

Tour Fort Sumter

Continue your history lesson with a visit to Fort Sumter National Historical Park. Fort Sumter is the island fort best known for being the site of the first shots fired in the Civil War. It was later the target of a union bombing campaign that lasted 15 months, leaving the original fort in ruins. Today, you can see the fort as it was rebuilt after the war.

A visit to Fort Sumter is fun for history buffs, but it also provides a chance to see Charleston from the water. Tours include a 60-minute roundtrip boat ride to reach the island. The trip provides a beautiful view of Charleston Harbor and the impressive Arthur Ravenel Jr. suspension bridge. Including the ferry ride, a visit to Fort Sumter takes about two and a half hours.

During our visit, we listened to a brief talk given by a park ranger about the history of the fort before exploring the ramparts, exhibits, and shoreline on our own.

Shop at Historic Charleston City Market

In the afternoon, explore the Historic Charleston City Market. The market is one the country’s oldest public markets and is a hub of tourist activity . It stretches four blocks and includes indoor and open-air stalls where vendors hawk goods such as artwork, jewelry, sweetgrass baskets, and clothing. Surrounding the market are tourist shops and boutiques, as well as several dining options. Each member of my family picked up a souvenir at the market to remember our trip.

Walk the Battery to Waterfront Park to Rainbow Row

Next, spend some time walking around the historic district. Seeing the city on foot should be an activity at the top of every Charleston must-do list. The historic district is located on a peninsula between the Ashley and Cooper Rivers and is filled with shops and restaurants, historic homes, museums, and parks. To see some of the best-known sites, start near the Battery and White Point Gardens.

The Battery is a seawall that runs along Charleston Harbor. Head north along the promenade, a wide path that follows the seawall. To your right, you’ll see the harbor, while on your left are some of Charleston’s most impressive homes.

Next, walk toward Joe Riley Waterfront Park, turning right on South Adgers Wharf. Inside the park, you’ll find Charleston’s iconic Pineapple Fountain. Children will also love to splash around in the fountain at the corner of Concord Street and Vendue Range. Afterwards, walk out along the Waterfront Park Pier to enjoy the view.

On the way back, stroll down East Bay Street, past the Old Exchange & Provost Dungeon until you reach Rainbow Row, a group of residences with colorful facades. You’ll finish back at White Point Gardens, a shaded park at the end of the peninsula. Note that you can easily reverse this route, starting and finishing near Waterfront Park, depending on where you park.

Day 3

Visit Patriots Point

Today, venture across the Arthur Ravenel Jr. Bridge to Mount Pleasant where you’ll find Patriots Point Naval & Maritime Museum. Patriots Point is home to the USS Yorktown aircraft carrier, the USS Laffey destroyer, and the USS Clamagore submarine. It also features 28 historic aircraft. Regular single-day admission allows you to board all three vessels and tour the Medal of Honor Museum and the Vietnam Experience Exhibit.

Patriots Point is the perfect destination for Charleston visitors with kids. I first visited as a teen and can still remember being impressed with the ships. If you’re up for a full day of historic sightseeing, you can combine the Fort Sumter tour described in Day 2 with the Patriots Point tour in today’s itinerary, as the Fort Sumter ferry boats also depart from Patriots Point. 

Spend Time at Mount Pleasant Memorial Waterfront Park

On your way back to downtown Charleston, stop at Mount Pleasant Memorial Waterfront Park, located at the base of the Ravenel Bridge. The park includes a war memorial, walking trails, a fishing pier, and a playground.

Have Dinner on Upper King Street

Tonight, have dinner on Upper King Street, a vibrant restaurant and bar scene where tourists and college students alike come to enjoy a night on the town. Popular restaurants include The Darling Oyster Bar, The Ordinary, and Prohibition. Afterwards, head for drinks at two more Charleston rooftop bars, Stars Rooftop & Grillroom and Pour Taproom. If you need a snack at the end of the night, pick up a giant 28-inch New York- style pizza from Benny Ravello’s “Home of the Virginia Slice.”

Day 4

Relax at a Charleston Beach

Being this close to the ocean, think about scheduling at least one day at the beach. The Charleston area has several great options within a 45-minute drive, including Folly Beach, Sullivan’s Island, Isle of Palms, and Kiawah Island. Charleston’s beaches offer powdery white sand, picturesque dunes, and cute beach villages. If you’re a surfer, rent a board at McKevlin’s Surf Shop in Folly Beach and catch some waves at The Washout. Later, grab a poke bowl and tropical drink on the patio of Wiki Wiki Sandbar on Center Street.

Day 5

Tour a Charleston-Area Plantation

Within a short drive of Charleston are several antebellum plantations, including Middleton Place, Magnolia Plantation & Gardens, Drayton Hall, Boone Hall Plantation, and McLeod Plantation. Two of these, Middleton Place and Magnolia Plantation, are known for their gardens, with Middleton Place claiming to have the oldest landscaped garden in the country. The gardens at Magnolia Plantation have picturesque bridges and ponds, while Middleton Place offers classical gardens set among gravel paths dotted with sculptures.

The original homes at both Middleton Place and Magnolia Plantation were destroyed in the Civil War. Today, you can see the Reconstruction-era buildings that were rebuilt on the properties. If antebellum architecture is your interest, consider visiting Drayton Hall, the only Charleston-area plantation with an original home open for tours.  

Where to Stay in Charleston

While there are many lovely, award-winning hotels in Charleston, we opted to stay in a vacation rental for our most recent visit. We chose a two-bedroom, two-bath apartment that had been recently updated, located two blocks from King Street. This charming rental is part of a larger Charleston-style home in the Cannonborough neighborhood and is within walking distance of many of Charleston’s top sights.

Read: Looking for ideas for other great trips around the Southeastern United States? Check out 8 Family Road Trips from Atlanta!