Pirates and Privateers Pub Crawl Tour in St Augustine

St. Augustine isn’t just the oldest city in America—it’s one of the most fought over. On the Pirates & Privateers Tour, you’ll walk through centuries of battle, betrayal, and buried treasure as you explore the haunted legacy of the men (and monsters) who once ruled the seas—and the coast of Florida.

 This 90-minute all-ages tour takes you deep into the stories of figures like Blackbeard, whose fearsome presence echoed up the Atlantic; Sir Francis Drake, who burned the city to the ground; and Robert Searles, whose brutal midnight raid changed the future of St. Augustine forever. You’ll learn about the siege that inspired the Castillo de San Marcos, a fort said to be haunted by the soldiers and prisoners who once bled within its coquina walls.

 Wander past the Oldest Wooden Schoolhouse and explore the mysterious legends tied to Ponce de León and his search for immortality. Along the way, you’ll hear chilling accounts of haunted forts, vanished settlements, and forgotten cemeteries—not to mention a few unquiet spirits who might be listening in.

 Whether you’re a fan of pirate lore, colonial conflict, or ghostly encounters, this tour brings St. Augustine’s wildest and weirdest history to life.