Ahoy! Set sail on a swashbuckling adventure through St. Augustine’s pirate past—family-friendly fun, hidden treasure tales, and high-seas legends await!

PRICE: See Booking Site

 

Full description
A Swashbuckling Family Adventure Through America’s Oldest City!

Ahoy, mateys! Prepare to hoist the sails and journey back in time on the Pirates & Pioneers walking tour—a family-friendly exploration of the legendary rogues, explorers, and treasure hunters who shaped the high-seas history of St. Augustine, Florida.

This history-packed tour invites pirates of all ages to uncover the real tales behind the myths, as your lively guide leads you through cobblestone streets, ancient forts, and hidden corners of the oldest continuously inhabited city in the U.S.

Discover how Juan Ponce de León landed on Florida’s shores, driven by dreams of gold and the mystical Fountain of Youth. Learn about his encounters with native tribes, his role in Spain’s conquests, and how his explorations set the stage for centuries of sea battles, shipwrecks, and buried treasure.

But it’s not all royal expeditions—this tour dives into the darker, more daring world of the Golden Age of Piracy, when infamous pirates prowled the Florida coast! You’ll hear thrilling tales of Blackbeard, who terrorized the Atlantic and may have even docked near these very shores. Learn about real pirate raids on St. Augustine, including an attack by pirates, who looted and burned the city in a midnight assault that still echoes in local legend.
See more

Highlights
Visit colonial streets once haunted by swashbucklers and smugglers
Learn about the weapons, tactics, and codes of honor (and dishonor!)
Perfect mix of education, humor, and excitement
Stops at historic landmarks and photo-worthy pirate hotspots
An unforgettable walk through over 500 years of history

Includes
Walking Tour
Knowledgeable Tour Guide
Tour Guide Gratuity

 

 

Explore thousands of upcoming events, local tours, top restaurants, and the best places to stay in Florida. You can also check out our dedicated city guide for Boca Raton, Clearwater, Daytona Beach, Ft. Lauderdale, Jacksonville, Miami, Orlando, Pensacola, Tallahassee, and Tampa.

 

Ready for an unforgettable weekend? Plan your trip around our Featured Events like Super Bowl Weekend, the Phoenix Open, NBA All-Star Weekend, Mardi Gras, CIAA, and more. Click here to see all Featured Events.