Ghosts and legends of Boca Grande: Part I

■ BY MARCY SHORTUSE – It isn’t hard to surmise that a place as old as Gasparilla Island has a few tales to tell – and not all of them are paradise-perfect. While we are now known as an elite island getaway location, just a few decades ago there was a more diverse population. From times of Cuban smacks bringing rum to Gasparilla Island to tales of pirates and Spanish royalty walking our shores, our reputation years ago was far from spotless. Haunts and ghosts still wander Gasparilla Island, having met their untimely end through many different means.
The pirate Gaspar was once believed to have chosen our island as a private lair, and is believed to have stashed female captives, jewels and gold on nearby islands. His blade is rumored to have spilled blood on our beaches more than once, and a spectral Spanish child princess has been spotted wandering the beach, in search of her head that was taken by Gaspar. The spirits of pirates who jumped ship instead of being captured haunt the rocks and wail in the waves pounding the shore at the south end.
There is the story of the lighthouse keeper’s daughter, a vibrant child who loved nothing more than to play in the upper rooms of the Port Boca Grande Lighthouse. Another girl, a teenager, still haunts a home on Park Avenue; the same place where she met her untimely demise. Welcome to part one of “Ghosts and Legends of Boca Grande,” a slightly darker side of the island that we call home. The tales of the pirate Gaspar Though they may be widely disputed, the tales of the pirate Jose Gaspar run rampant all along the Florida coast.
Pirates who are still celebrated in huge festivals and with much “pirattitude.” The Jolly Roger flag, once feared in local waters, can now be seen on shirts, bumper stickers and banners everywhere. Jose Gaspar, or Gasparilla, 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 the 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 island being haunted have spread far and wide, 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 place for treasure 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.
One night this local guide went out by himself, and as he pulled up his engine stalled. As he sat back for a moment he felt something very large move in the water next to the boat, and it rocked as though someone was climbing up and into it. The guide said he did what he had to do to get out of there – and quick. Others are rumored to have heard the faint sounds of an off-key piano coming from the island, and the cries of a baby as well.
The legend of Josefa the Spanish princess is one of the most widely known around the area. The young girl taken captive by the infamous pirate was royalty, and Gaspar was smitten. He kept her at his private home on Gasparilla Island, away from his other female captives on Captiva. She would have none of him, though, and in a fit of rage one night he chopped off her head. Instantly contrite, Gaspar bemoaned his choice and, with great fanfare, took her body to be buried on its own nearby island. It is now called Useppa.
Legend has it that Gaspar kept Josefa’s head for a long time, so he could continue to gaze upon her beauty for as long as possible. Though it’s been awhile since Josefa has been seen wandering the beach by Banyan Street, her spirit is said to still live there, wandering around, looking to become complete again. See next week’s Boca Beacon for more Ghosts and Legends of Boca Grande.