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Old Charleston Jail

Old Charleston Jail: Our most recommended tours and activities

Charleston: Pirates and Ghosts Guided Walking Tour

1. Charleston: Pirates and Ghosts Guided Walking Tour

Interested in exploring Charleston from the perspective of Pirates and Ghosts? Want to really immerse yourself in the history of this great Colonial city, right from the locations that started it all? You can get the best of both worlds with this 2 in 1, history-based guided tour of Charleston’s most infamous pirate and ghost stories, right from the streets they once (and still) roam. Notable stops are old pirate bars, haunted cemeteries and the old prison which housed many of the world’s most famous pirates. The tour will end at the old city jail which is only 2 blocks away from King St. Throughout the tour you will learn about the history of Pirates and Ghosts in Charleston. Learning about pirate battles from the likes of Blackbeard and the Gentleman pirates that resided in city as we stop at the Pineapple fountain, south of broad, and the Pink House. You will learn about spooky ghost stories that occurred right here in Charleston from throughout our stops at the Old Exchange building and the Old City Jail.

Charleston: Self-Guided Ghost Tour

2. Charleston: Self-Guided Ghost Tour

Hear scary stories, discover spooky legends, and learn about Charleston's dark side on an eerie self-guided walking tour. Charged smartphone in hand, set out on a ghoulish tour that takes you to Charleston's most haunted sites. Listen to ghost stories like the legend of the woman in black, the haunting of the Dock Street Theater, St. Philips Church and the Ghost of the Weeping Woman, and many more. Stop outside haunted pubs, using the opportunity to refuel with a quick bite or beer before continuing your adventure. The tour is app-based and uses GPS navigation, so you can go at your own pace and take the tour at any time, even exploring the city during the witching hour if you like. 

Charleston: Southern Charm Walking Food Tour with Tastings

3. Charleston: Southern Charm Walking Food Tour with Tastings

On this guided food tour, stroll through the streets of Charleston for two hours and discover four favorite local eateries. While you sample the delights of Southern cuisine, learn about the history behind the dishes. Along the way, pause to see landmarks like the Old Charleston Jail. To begin your tour, head to the classy and iconic eatery "82 Queen" to meet your guide and dive into the tastings. At this stylish establishment, sample a creamy she-crab soup that was originally created to impress President William Taft. Savor the rich blend of seafood flavors. After you've whet your appetite, make your way to see the sights of Charleston and meander to 60 Bull Cafe. Here, tuck into a mouthwatering, freshly-caught flounder po'boy. Learn about the history pimento cheese, a uniquely Southern, creamy cheese experience. Continue as you stroll past the sights of Charleston, including Old Charleston Jail and Wentworth Mansion. Snap photos as you go, then stop at a third eatery for a classic sweet tea and deviled egg pairing. Finally, visit Vom Fass for a tasting of gourmet olive oils and liqueurs.

Charleston: 2-Hour Strong Women of the South History Tour

4. Charleston: 2-Hour Strong Women of the South History Tour

The Strong Women of the South History Tour is an exploration of historical Charleston from the perspective of the founding mothers and women of every color who contributed to the Great American Dream. Along the way, learn about a city once owned and controlled by women. Rated as a top Airbnb experience by Charleston Weddings Magazine, this tour is perfect for bachelorettes, couples, locals, and tourists who are looking for something more than a generic city tour. This experience begins at the alleged execution site of America's first female serial killer. Stand in the spot where she met her fate and hear her story. Next, visit the homes and sites of the “Old Maids." Learn about these women who were activists, printers, artisans, madams, shopkeepers, and plantation owners while hearing stories about their contributions and conundrums. Go back in time and see the world from their perspective. Lastly, stand in front of the homes and shops of the women who built this city. Hear their stories in the contemporary voice of their times and smash the myth of the "Fainting Southern Belle," the "Woman behind the man," and Chattel Slavery. From each ticket sold, $1 will be donated to the Halsey Contemporary Art Foundation and the Philip Simmons Foundation.

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Other Sightseeing Options in Old Charleston Jail

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What people are saying about Old Charleston Jail

Overall rating

4.0 / 5

based on 3 reviews

It was a nice walk but we would have preferred if it ended up back where we started instead of having to walk so far back to get to our car.