Choose Your Experience
Explore nearly three centuries of Charleston's history through the era that interests you most.
Rather than covering centuries in a single tour, choose a small-group experience centered on one of Charleston's most fascinating historical periods. Whether you're drawn to Colonial Charleston, the Golden Age of Piracy, Reconstruction, the Gilded Age, Temperance, South Carolina's Dispensary Era, World War I, the Roaring Twenties, Prohibition, the Great Depression, or Charleston's evolving social landscape, each experience offers its own unique stories, locations, atmosphere, and pace.
Choose from immersive walking tours or historic pub crawls where stories continue during carefully selected tavern stops. Pub crawl experiences include opportunities to purchase beverages while exploring Charleston's historic drinking culture. Drinks are not included.
1670–1740: Colonial Charleston & the Golden Age of Piracy
Shadows, Sailors & Smugglers
A family-friendly walking tour exploring Colonial Charleston through pirates, privateers, smugglers, maritime commerce, colonial law, waterfront life, taverns, and the people who helped shape one of America's oldest cities.
Tides, Tankards & Treachery
A 90-minute historic pub crawl exploring Colonial Charleston with one carefully selected tavern stop where stories continue while guests enjoy opportunities to purchase beverages.
The Drunken Sailor
A two-hour historic pub crawl beginning in an English-style pub, continuing through an immersive one-hour guided walk, and ending in an Irish pub while exploring pirates, merchants, taverns, maritime history, and Charleston's colonial waterfront.
1870–1940: Charleston's Changing City
Sidebars & Sidecars
A history-focused walking tour exploring Reconstruction, the Gilded Age, Temperance, South Carolina's Dispensary Era, World War I, the Roaring Twenties, Prohibition, the Great Depression, architecture, politics, and Charleston's changing culture.
Haint Life Grand
A historic pub crawl exploring the same remarkable era through Charleston's taverns, hotels, and gathering places while learning about changing drinking culture, local personalities, Prohibition, and everyday life.
Depending on the experience you select, topics may include Colonial Charleston, pirates, privateers, maritime commerce, taverns, Reconstruction, Temperance, the South Carolina Dispensary Era, World War I, the Roaring Twenties, Prohibition, the Great Depression, architecture, politics, and everyday Charleston life.
Small groups encourage conversation, questions, and interaction throughout every experience. Routes and participating taverns vary by option selected.
