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Pirate History Around Pine Island Florida....

Pine Island Real EstateThose of us who are fortunate enough to live among the islands of Florida's Southwest Coast know that hidden deep within the murky roots of mangroves, and buried far below the sand and shells, are3 the legends of the saltwater bandits. 

Pirating was among the hardest and most dangerous of the early colonial occupations but it often paid extremely well. To this day, pirates and hidden treasure live on in the lore of Pine Island, Captiva, Sanibel, Boca Grande, Cayo Costa and Useppa.

Pine Island Real EstateJose Gaspar, self-proclaimed King of Pirates, established a small kingdom on Gasparilla Island or Boca Grande. A member of an old Spanish family, he had entered the Spanish navy at age twelve and had risen rapidly until the day he was entrusted with some of the crown jewels. He absconded with them and turned pirate. His method was to kill all the men on captured ships and then install their ladies as members of his harem. In 1821 he planned to retire but went after one more vessel. It turned out to be an armed American ship. Trapped, he tied a cable chain about his wrist and leaped overboard to his death. Although most of his crew were either drowned or hung by the Americans, some escaped into Pine Island Sound in a yawl. His chief gunner, Black Augustus, remained on Black Island in Estero Bay, Juan Gomez stayed at Panther Key for a time, one managed to make his way back to Cuba and nothing is know of the rest who had been left on Boca Grande to guard the treasure.

Bru Baker, an old friend of Jose Gaspar, at one time berthed his ship at Boca Grande but this was a short-lived arrangement. Baker's crew had a bloody war with Gasparilla and ended up building a small encampment at Bojelia, or Bokeelia, at the head of Pine Island. In 1819 he got wind that the United States wanted to purchase Florida from Spain. Gathering his hidden treasures and dividing some of the sp09nls with Gasparilla, Bur Baker and crew left our waters. Heading for Cartagena, he was killed by the poisoned arrow of one of the native Indians on the Gulf of Darien. Whether or not some of his treasure was forgotten here on our little island is purely conjecture...but who knows?

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You could almost call Pine Island the "anti-Florida. No crowed beaches. No high rise condos. No fancy resorts. No sprawling subdivisions. But to these who live there, it represents all that Florida used to be. It's more than just an island; it's a way of life, much as it's been since the first white settler put down roots in 1873.


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Carl Jervis, Licensed Florida Real Estate Broker
Office: 5459 Pine Island Rd   Bokeelia, Florida  33922
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