Florida’s Pirate History

Historic Pirate Map of the Stump Pass Coastline
This map is also printed on the back of our Pirate Poker Run event shirts!

Englewood Beach Waterfest’s Pirates Poker Run pays homage (albeit festive light-hearted fun) to the rich, romantic, and exciting Pirate legends surrounding the Florida peninsula and their rum-soaked yarns of buried ill-gotten loot!

Treasure Chests of shiny gold doubloons, hand-crafted gemstone bedazzled artifacts, leather-wrapped folds of diamonds, emeralds, rubies, sapphires, topaz, pearls, ivory, and turquoise, and sunken ship’s ballast in piles of cast silver ingots.

Nineteen-year-old Spanish conquistador Juan Ponce De LeÓn sailed aboard Christopher Columbus’s second expedition to the New World in 1493 arriving in Hispaniola.

Ponce De LeÓn returned twenty years later in 1513 landing on Florida’s East Coast aboard his armada of Spanish galleons, mapping the coastline down to the Keys and around, up the Gulf coast at least to the bay of Charlotte. 

Ponce De LeÓn returned to Spain in 1514 where he was knighted by King Ferdinand, declared the Governor of Hispaniola, and was authorized to settle Florida as a Spanish Crown colony.

Nobleman Ponce De LeÓn returned to Hispaniola in 1516 and sailed back to Spain in 1517. With each trip, Ponce De LeÓn plundered as much gold as could be tortured out of the natives. In March 1521 Ponce De LeÓn finally set foot once again in Florida to begin colonization. Unfortunately for the Spanish Crown the native Calusa peoples thought otherwise and fiercely fought back their overwhelmingly armed foes.

Ponce De LeÓn was severely injured and retreated with his armada to Cuba where he died of his wounds in July, temporarily ending Spain’s New World exploitation. His body was entombed in Hispaniola, now known as Puerto Rico.

Ponce De LeÓn is generally credited with discovering Florida although concealed and censored ship logs reveal rogue Spanish slave ships captured natives in the Bahamas as early as 1494.

Ponce De LeÓn’s death in 1521 marks the transition to Florida’s golden Pirate era.

Perhaps the most notorious pirate to roam the Caribbean was Sir Francis Drake,yes, the same Francis Drake who circumnavigated the globein 1577-80 was known as the pirate El Draque.

Real-life pirates in the Caribbean Sea were violent thieves, so desperate to avoid capture that torture and murder were everyday occurrences. Pirates’ careers were very short-lived, and the lineup of replacements was never-ending.

The most successful Caribbean pirates operating in and around the Florida Gulf coast were Henry Avery, “Pirate Black Sam” Bellamy, Anne Bonny, Howell Davis, Captain William Kidd, Edward Low, Captain Henry Moran, John “Calico Jack” Rackman, Mary Reed, Keith Richards (the Jack Sparrow character), Bartholomew “Black Bart” Roberts, Robert Searle, Edward “Blackbeard” Teach, and Charles Vane.

Florida’s Gulf coast was the perfect secluded pirate realm. When trailed Pirates darted into the uncharted Intracoastal waters to evade capture because they knew the waters, and the pursuing authorities did not and quickly wreck.

An estimated 5,000 pirates roamed Florida’s Gulf Coast between the peak pirate years of 1715 to 1735.