A Weekend of Pirates and Southern Charm

To dive into Charleston's pirate history, start your weekend where it all began—in Charleston Harbor. In the city's early days, the harbor served as its front door, with a constant flow of ships connecting it to the world. Some of those ships were the pirate kind.

It was in Charleston Harbor that the famous Blackbeard set up a blockade and held the entire city hostage in 1718. Nothing could get in or out of the harbor until Blackbeard's demands were met. Rather than money, gold or power, he was after mercury, which was then the only known treatment for syphilis. After six days, the medicine was delivered, and Blackbeard freed the city and sailed away.

Not all pirates made a clean getaway like Blackbeard. Many faced execution at the public gallows located nearby at White Point. Among those hanged was Stede Bonnet, known as the "Gentleman Pirate." You'll learn more about him later.

Today, White Point Garden is a beautiful park at the tip of the Charleston peninsula, where the Ashley and Cooper rivers flow into the harbor. The park features sun-dappled lawns and majestic live oaks. Kids can run on the grass, swing from the trees and explore ancient cannons and piles of cannonballs that appear ready for action, all while enjoying views of the water. Parents can appreciate the beauty and history, and everyone can start to think like a pirate as they shake off travel weariness.

End the evening with dinner at Lowland. Nestled in a historic house behind The Pinch Hotel, Lowland is a modern, elegant tavern inspired by the classic roadhouse style of 19th-century England, but reinterpreted for the Lowcountry.

If you’re looking for something more kid-friendly, head to Taco Boy, a lively taqueria filled with authentic Mexican artwork and, of course, delicious tacos.

Rise and shine, matey! You have a very full day ahead.

Start your morning with a hearty, pirate-worthy breakfast at Millers All Day on King Street, where you can fuel up on grits, biscuits and their famous cinnamon rolls before setting sail on your adventure. If you're in the mood for something quick, Callie’s Hot Little Biscuit offers grab-and-go Southern goodness that kids and adults alike will love.

Start your day with Charleston Pirate Tours. Your tour guide will be hard to miss: a swashbuckling pirate with a tricorn hat, long cutlass and macaw perched on his arm. This lively walking tour lets you see Charleston through the eyes of an 18th-century pirate, complete with stops at pirate hotspots and captivating storytelling.

As you walk, you'll learn not just about Blackbeard, but also lesser-known—and perhaps more intriguing—pirates like the “Gentleman Pirate” Stede Bonnet, who was simply having a midlife crisis, and Mary Read, whose bold escapades could make any teenager’s rebellion look mild. Expect pirate lingo, lore and plenty of myth-busting along the way.

All that walking will build up an appetite.  Lucky for you, you'll have far more options than the typical pirate diet of hardtack, salted meat, limes and gin.

For lunch, grab a table at Fleet Landing, a waterfront favorite that’s both scenic and family-friendly. The kids will love watching boats float by while you enjoy fresh seafood, fried green tomatoes or a classic po' boy sandwich. It’s casual, coastal and perfectly Charleston.

Prefer something a bit more casual? Brown Dog Deli is a short stroll away, with a fun, eclectic menu and a great kids' selection. 

Known for its Southern classics and bistro setting, FIG’s seasonal menu pays homage to the Lowcountry with dishes like blue crab ravioli and white shrimp escabeche. 

In the afternoon, explore the darker side of pirate life. 

Life on the high seas wasn't all adventure and treasure; sometimes, pirates got caught. And jail was not a place you'd want to be in the early 18th century. Head over to the Old Exchange and Provost Dungeon to see just how grim things could get when pirates were caught. The main and upper floors of the building are filled with light and rich history, but the basement? The basement is, well, a dungeon.

A costumed tour guide will take you through the low-ceilinged and musty bowels of the building and explain what life was like for a prisoner while life-sized dioramas bring the stories to life.

Once you've had your fill of eerie tales and echoing footsteps, lighten things up with a visit to the Children's Museum of the Lowcountry. Kids can climb aboard the museum’s pirate ship, dress in full buccaneer regalia and even walk the plank. Meanwhile, parents can kick back and enjoy a moment of peace—and maybe a coffee.

Wrap up your day with a relaxed dinner at Home Team BBQ, where the laid-back vibe, cornhole games and kid-friendly menu make it a family favorite. Or, if you're craving a little something fancier, Poogan’s Porch serves Southern classics in a charming Victorian house—fried chicken, mac and cheese and pimento cheese biscuits included.