The tale of the pirate Gaspar and his sweet Joseffa ... Though they may be widely disputed, the tales of the pirate Jose Gaspar run rampant all along the Florida coast. The Jolly Roger flag, once feared in local waters, can now be seen on shirts, bumper stickers and banners everywhere. Jose Gaspar, or Gasparilla as he was called, supposedly lived in the mid-1700s and roamed our coastline during the late 18th and early 19th centuries. Gasparilla Island was his headquarters, and his crew lived on nearby islands such as Cayo Pelau. Gaspar housed his female slaves on nearby Captiva Island. He and his pirates allegedly led quite the merry life, until one day in December of 1821. He and his crew were in full retirement mode, legend says, and were divvying up their ill-gotten booty. Their plan was to go live the quiet life ... until they saw that beautiful, sleek British merchant ship on the horizon. Their greed got the best of them, and they set out on one more piracy adventure. As they approached the Union Jack was dropped and the American Flag was revealed. It was the pirate-hunting schooner U.S.S. Enterprise, and they commenced to battle with Gaspar’s pirates. The pirates were painfully trounced, and it is rumored that as he was facing capture he tied an anchor around his waist and announced, “Gasparilla dies by his own hand – not my enemy’s!” and he leapt overboard. Many other pirates died that day, just off the shore of Gasparilla Island. In all, other than Gaspar it is said that 35 pirates were strung up from the yardarm. Cayo Pelau, a 124-acre island just to the east of Gasparilla Island, is said to have been the old quarters for most of the pirate band. The stories of the 46GASPARILLA ISLAND September/October 2017 island being haunted have spread far and wide, and through several generations of Boca Grande families. There was a spot there called “Low Town,” where the pirates lived, drank and caroused with murderous glee. While the lowly pirates cavorted on Cayo Pelau, Gaspar the Pirate led a more refined existence on Gasparilla Island. Some say Gaspar’s men had their own hiding places on Cayo Pelau, and their ghosts still guard the undiscovered treasure. More than a handful of treasure hunters have had good intention to check out Cayo Pelau over the years, only to find their boat motors would mysteriously quit working on the way there. Metal detectors that worked perfectly anywhere else would suddenly falter and die on Cayo Pelau. One captain said as he approached the island his vessel started taking on water for no apparent reason. Once he got home, no leaks were ever found. An east coast fortune hunter tried numerous times to make it to the island in his own boat, but each time unexplained cold fronts, driving rain, windstorms, prop or engine trouble would pop up. “There’s something wrong at Cayo Pelau,” he was quoted as saying in a news article. A local fishing guide recalled trips out to the small island when he was a boy. He and his friends would taunt each other by heading out there in their small boats at night sometimes, and see who was brave enough to go ashore.
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