St. Augustine Pirate Walking Tour Adventure

Step into a world of mutiny, mystery, and maritime mayhem! This 90-minute walking tour through historic St. Augustine plunges you into the Golden Age of Piracy—when cannon fire echoed across the bay and treasure was real.
Follow in the footsteps of notorious pirates like Sir Francis Drake, who burned the city, and Robert Searles, whose surprise raid devastated the town. With 22 documented pirate attacks, St. Augustine holds more buried secrets than any port on the Atlantic—and we’re digging them up for you.

Hear untold stories, face the fear, and take home a replica treasure map said to be inspired by a condemned pirate’s final act. Every young buccaneer also leaves with treasure!

This isn’t just a tour—it’s an immersive plunge into the gripping, gritty, and often gruesome world of piracy in America’s oldest city.

Are you brave enough to uncover the truth behind the legends?

Meeting Point

10 S Castillo Dr

10 S Castillo Dr, St. Augustine, FL 32084, USA

Guests will meet our guide in front of the visitor center by the steps

What's included:

• Treasure for Kids!
• Guided Tour
• Treasure map

What to expect:

Duration: 1 hour, 30 minutes

Castillo de San Marcos National Monument

1 S Castillo Dr, St. Augustine, 32084-3252, Florida

The Castillo de San Marcos is the oldest masonry fort in the continental U.S., built by the Spanish in 1672 to protect St. Augustine. Its coquina stone walls withstood attacks and still stand strong. Visitors can explore its storied past of battles, pirates, and colonial power struggles right on the bayfront.

Pass by without stopping

Plaza de la Constitucion

1 Cathedral Pl, St George Street between King Street and Cathedral Place, St. Augustine, 32084, Florida

The Plaza de la Constitución is the heart of historic St. Augustine and the oldest public space in the U.S., dating to 1573. Surrounded by colonial architecture, it has witnessed centuries of history, from Spanish rule to civil rights protests. Today, it hosts events, monuments, and a lively community atmosphere.

Pass by without stopping

Saint Johns River

St Johns River, Florida, USA

Pirates once prowled the Matanzas River in St. Augustine, lured by Spain’s treasure-laden ships and the city's strategic port. The river was a gateway—and battleground—for infamous raiders like Sir Francis Drake and Robert Searles, who attacked and plundered the settlement. Hidden coves and twisting inlets offered perfect hiding spots for pirate ships, while cannon fire from the Castillo de San Marcos defended the city’s shores. Today, the river may be calm, but its waters still whisper tales of gold, gunpowder, and daring escapades that shaped St. Augustine’s swashbuckling past.

Pass by without stopping

St. George Street

St. George St, , St. Augustine, 32084, Florida

St. George Street is the lively heart of historic St. Augustine, filled with charming shops, cafes, and centuries-old buildings. Once a colonial thoroughfare, it now invites visitors to stroll through history, offering a vibrant mix of culture, cuisine, and local treasures in a pedestrian-only setting.

Pass by without stopping