St. Augustine Pirates & Privateers Cocktail Tour
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Overview
Pirates and Privateers Cocktail Tour in St. Augustine invites guests to step back in time and explore the city's swashbuckling past. This walking tour delves into the lives of pirates and privateers who shaped St. Augustine's history, revealing tales of adventure, plunder, and intrigue.
Participants can expect to visit some of St. Augustine's most historic taverns and pubs, raising a glass with fellow adventurers while hearing stories of legendary figures like Blackbeard, Ponce de Leon, and Sir Francis Drake. The tour includes stops at notable landmarks such as the Pirate Pub Crawl, Pirate's Ghost Toast, The Oldest Wooden Schoolhouse, The Queen's House, St. Augustine Sea Wall, Triumphant Military Leader Memorial, and Castillo de San Marcos, each adding depth to the pirate narrative.
The experience includes a historically accurate cocktail tour, expert guidance, and exploration of key historical sites. It excludes gratuities and alcoholic beverages (for 21+ only). This small-group walking tour offers a unique blend of history and pub crawling, perfect for those seeking an engaging and spirited adventure through St. Augustine.




Highlights
Discover Pirate History: Learn about the pirates and privateers of St. Augustine.
Explore Historic Taverns: Visit some of St. Augustine's oldest and most interesting pubs.
Walk the Ancient City: See famous landmarks and hear captivating stories.
Small Group Experience: Enjoy a more personal and engaging tour.
Sentiment Analysis
Customers enjoyed the historical facts, tour guide, and walking the city. Customers wished the drinks were included in the price.

Visitors enjoyed the tour guide was very good.
Visitors enjoyed the stories that the tour guide had to tell.
Visitors say it's a great way to spend time when visiting St. Augustine.
Visitors enjoyed the walking and exploring St. Augustine with a guide.
Visitors wished that the drinks were included in the ticket price.
Visitors say it's a lot of walking and standing, so wear comfortable shoes.
The Journey
Pirate Pub Crawl
Step back into St. Augustine's swashbuckling past with a spirited Pirate Pub Crawl! Raise a glass to notorious sea dogs, daring raids, and rum-soaked legends that shaped the city's maritime history. Explore the real stories behind the myths, from cannon fire to Caribbean conquests, all while responsibly enjoying the local taverns. It's a toast to danger, debauchery, and a rousing good time in America's oldest city.
Pirate's Ghost Toast
Follow the footsteps of a fearsome pirate, whose shadow loomed large over Florida’s coast. Raise a glass to his brutal battles, buried treasures, and the wild myths that made him a maritime legend. A pirate's spirit remains in St. Augustine, and if you are brave enough, you will have the opportunity to toast to this ghost.
The Oldest Wooden Schoolhouse
Venture into the heart of historic St. Augustine to discover The Oldest Wooden Schoolhouse, a unique window into early American education. Dating back over 200 years, this humble red cedar and cypress structure, secured by massive anchor chains, has weathered centuries of storms and stories. Experience a tangible connection to the past within this remarkable survivor.
The Queen's House
Visit "The Queen's House," a tribute to Queen Joanna of Castile, the Spanish monarch whose reign defined the golden age of exploration. Her influence guided Spain’s early conquests, including the founding of St. Augustine. Learn of the fiery siege launched on the fledgling settlement in 1586 by Sir Francis Drake, just steps away, revealing the city's turbulent beginnings.
St. Augustine Sea Wall
Explore the St. Augustine Sea Wall, the city’s enduring first line of defense against invaders and the relentless tides of Matanzas Bay. Today, it stands as a symbol of St. Augustine’s resilience, offering scenic views and a timeless reminder of how the past still guards the present. Walk along this historic landmark and witness the city's unwavering spirit.
Triumphant Military Leader Memorial
At this location, explore the remarkable story of a triumphant military leader and defender of freedom in colonial St. Augustine. Serving under the Spanish crown, he bravely protected the city from British attacks. Discover how his bravery and leadership became a symbol of resistance, resilience, and the enduring fight for liberty in America’s oldest city.
Castillo de San Marcos
Stand in the shadow of the Castillo de San Marcos, St. Augustine's enduring stone sentinel. This formidable fortress once faced down fierce threats from the sea, including pirates and privateers hungry for Spanish gold. Uncover dramatic tales of cannon fire, coastal defense, and the ruthless men who tried—and failed—to claim the city by force. Discover how history was forged here, one cannonball at a time.
Tour's End - Refreshments Available
Conclude your historical exploration at this location, where you can purchase an alcoholic beverage and reflect on your journey through St. Augustine's captivating past. Raise a glass to the city's rich history and unforgettable tales as your tour comes to a satisfying end.
Know Before You Go
This historically accurate cocktail tour explores the history of piracy and exploration in St. Augustine. The tour includes the guidance of an expert, but does not include gratuities or alcoholic beverages (must be 21+ to purchase). This is a walking tour, so wear comfortable shoes. Enjoy exploring!
Hot Tip
Wear comfortable shoes. You will be walking a lot and standing. Some visitors wished that the drinks were included in the ticket price, so be prepared to pay extra for drinks at each stop.