Ahoy, matey! Step into the swashbuckling past of St. Augustine, where pirates, privateers, and plunder once ruled the coast. On this spirited pub crawl through the nation’s oldest city, you’ll raise a glass to notorious sea dogs, daring raids, and rum-soaked legends that helped shape St. Augustine’s wild maritime history. From cannon fire to Caribbean conquest, we’ll explore the real stories behind the myths—one drink at a time. So grab your grog and prepare to pillage the past… responsibly, of course. Cheers to danger, debauchery, and a rousing good time!

Follow in the footsteps of the most feared pirate to ever sail the seas— whose shadow loomed large over Florida’s coast. We’ll raise a glass to his brutal battles, buried treasures, and the wild myths that made him a maritime legend. Are ye brave enough to toast a pirate's ghost?

Nestled in the heart of historic St. Augustine, the Oldest Wooden Schoolhouse offers a rare glimpse into the early days of American education. Dating back over 200 years, this humble red cedar and cypress structure has weathered centuries of storms and stories—secured by massive anchor chains to survive hurricanes.

"The Queen's House"—pays tribute to Queen Joanna of Castile, the Spanish monarch whose reign marked the golden age of exploration. Her influence stretched across the Atlantic, guiding Spain’s early conquests, including the founding of St. Augustine. Just steps away, in 1586, Sir Francis Drake launched a fiery siege on the fledgling settlement.

The St. Augustine Sea Wall has long stood as the city’s first line of defense—not just against invaders, but against the relentless tides of Matanzas Bay. Today, it remains a symbol of St. Augustine’s resilience, offering scenic views and a timeless reminder of how the past still guards the present.

At this stop, learn about a triumphant rise of a military leader and defender of freedom in colonial St. Augustine. Fighting under the Spanish crown, he helped protect St. Augustine from British attacks. Bravery and leadership that became a symbol of resistance, resilience, and the enduring fight for liberty in America’s oldest city.

At this stop, you will learn about the Castillo de San Marcos that was St. Augustine's standing stone sentinel over St. Augustine, the Castillo de San Marcos once faced down some of the fiercest threats from the sea—pirates and privateers hungry for Spanish gold. From daring raids to bloody sieges, this fortress withstood attacks. Uncover the dramatic tales of cannon fire, coastal defense, and the ruthless men who tried—and failed—to claim the city by force. History was forged here, one cannonball at a time.

At this stop, you will have the opportunity to purchase an alcoholic beverage. Your tour will end here.