Updated October 2026
The short answer
The best things to do in downtown Charleston are a sail on Charleston Harbor, Rainbow Row, the Battery, the City Market and Waterfront Park, plus the historic homes, churches and museums in between. Most are within walking distance of each other on the peninsula.
1. Sail Charleston Harbor
See the whole city at once from the water: the Battery, the steeples, Fort Sumter, the Ravenel Bridge and the USS Yorktown. A private sunset sail or daytime sail on Esprit de Joy is 2.5 hours for up to 6 guests, with dolphins often joining along the way.
2. Rainbow Row
The row of pastel historic homes on East Bay Street is Charleston’s most photographed street. Go early in the morning for the best light and fewest people.
3. The Battery and White Point Garden
The seawall promenade at the tip of the peninsula has harbor views, grand historic homes and shady live oaks.
4. Charleston City Market
Four blocks of vendors, including sweetgrass basket makers carrying on a Gullah tradition. It’s one of the oldest public markets in the country.
5. Waterfront Park
Lawns, a long pier with porch swings and the Pineapple Fountain, all right on the harbor.
6. St. Michael’s Church
Built in the 1750s, St. Michael’s is one of the oldest churches in Charleston, and its white steeple is a landmark you can see from the harbor.
7. Nathaniel Russell House
A restored 1808 townhouse famous for its free-flying spiral staircase. Tours cover the family who lived there and the enslaved people who worked there.
8. The Old Exchange and Provost Dungeon
A colonial-era building with a dungeon underneath, and one of the best places to learn the city’s Revolutionary War history.
9. Circular Congregational Church
Home to a congregation dating to the 1680s, with a distinctive round sanctuary and one of the oldest graveyards in the city.
10. The International African American Museum
Opened in 2023 at Gadsden’s Wharf, where many enslaved Africans first arrived in North America. Its genealogy center helps visitors trace their family history.
Why the harbor belongs on your list
- It’s the city’s best view. You see the skyline, the forts and the bridge in one afternoon.
- It’s relaxing. After a day of walking, sitting on deck with a drink is a welcome change of pace.
- It’s history. Charleston was built on its harbor, from colonial trade to the first shots of the Civil War at Fort Sumter.
- It’s private. Your own boat and captain, your own playlist, BYOB.
Common questions
What is the number one thing to do in Charleston? Most visitors start with Rainbow Row and the Battery. To see the whole city at once, take a sail on Charleston Harbor.
Where do Charleston sailing charters leave from? Ours leave from The Harborage at Ashley Marina, 33 Lockwood Dr, about 10 minutes by car from the City Market.
How long should I spend in downtown Charleston? Two to three days lets you walk the historic district, take a harbor sail and visit a museum or historic home.
See downtown from the water
Every charter is private, 2.5 hours and up to 6 guests. Check available dates, or compare the Private Sunset Charter and the Private Daytime Charter.
