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Pirates of St. Augustine!

Pirates Roam Nightly in Ancient Florida City

Although the infamous Black Pearl of the “Pirates of the Caribbean” never sailed into St. Augustine’s harbor, the nation’s oldest city was a regular stop for some of the most notorious pirates of the Spanish Main.  Today, visitors are not only enthralled by true stories of bloody pirate raids on the town, nearly every night of the week offers them a chance to sail across moonlit Matanzas Bay with some of the most colorful scoundrels who ever waved the Jolly Roger.

As the most northern outpost of Spain’s Empire in the New World, St. Augustine was of vital importance to the treasure fleets.  Whether they were carrying the treasures of Aztec Mexico or the riches of South America, the captains of Spain’s annual treasure fleets depended on St. Augustine as a source of refuge on the long trip home.  It was the last “rest stop” before the crossing of the open Atlantic to Spain.  For pirates, St. Augustine offered the perfect spot to ambush a straggler from the fleet or to come ashore and help themselves to riches stored for safe keeping.

The first great pirate raider to lay waste to the city was the famous English corsair Sir Francis Drake.  In 1586, on his way home from sacking the Spanish city of Cartagena, Colombia, Drake’s men noticed a signal fire maintained each night by the Spanish on top of a tower near the present location of the St. Augustine Lighthouse.  Realizing there was a Spanish town nearby, Drake led more than 2,000 of his raiders ashore where they destroyed St. Augustine and hauled away anything of value.

In 1668, the notorious Jamaica-based pirate Robert Searles captured a Spanish ship and sailed it boldly into St. Augustine’s harbor.  He and his men then stormed ashore, overpowered the surprised garrison, and ran rampant through the town murdering and pillaging along the way while enslaving any resident judged not to be “full-blooded” Spanish.  Among the 60 townspeople killed by the pirates was a 5-year old girl murdered by Searles.  According to legend, her ghost haunted him until he went mad and killed himself years later.  Largely as a result of this raid, the Spanish built the massive Castillo de San Marcos fortress which served to discourage the frequent pirate raids that had plagued the city for so long.

Each June, Drake’s devastating raid is re-enacted in what has become one of the largest and most authentic depictions of 16th century warfare in the United States.  Likewise, March brings a re-enactment of the horrible Searles’ Raid complete with sword clashes and musket fights between Spanish defenders and rampaging pirates in St. Augustine’s streets.

But for those who need a more frequent swashbuckling adventure, several attractions are available to satisfy the desires of even the heartiest sea rogue.  For example, each night the 72-foot schooner Freedom leaves the dock on a quiet sail beneath the stars.  For passengers, the cruise takes on a whole new dimension when they suddenly find themselves face-to-face with a pirate named Wiggins who sailed with Robert Searles.  Lots of sea chanteys, grog, tall tales and audience participation lead to a fun and memorable experience for everyone. For more information, go to www.aghostlyexperience.com and select “Sailing Tour” from “Our Tours”.

On Friday, Saturday and Sunday nights, the city’s Harbor Shuttle is commandeered by pirates who take their passengers across Matanzas Bay to a secret island location in Salt Run.  With a hearty “yo-ho-ho and a bottle of rum” they dig up an impressive treasure chest.  Returning to the boat, they divide their treasure among the passengers and induct them into the fraternity of pirates.  The trip also includes a wealth of pirate lore and tradition.  More details are available at www.harborshuttletours.com under “Pirates of the Matanzas”.

To find out more about attractions, history, and accommodations in St. Augustine, Ponte Vedra and the Beaches contact the Visitors and Convention Bureau at 1.800.OLD-CITY (2489) or go to www.VisitOldCity.com .

Edited by Dave Shultz

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