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About:  Some 24.5 million years ago, Pine Island rose, as did Florida, from the receding seas.  It is not known when man first arrived on our island, but skeleton remains have been unearthed dating back about 6,000 years. Calusa Indians were thought to have inhabited the island in peace from 300 AD until 1513 when it's believed Ponce De Leon landed on the west side of Pine Island.  The Spanish not only fought the Calusas but introduced diseases they had no immunity to, wiping them our by the 1700's.  An important archeological dig is located in Pineland, a small community on northwest Pine Island, thought to have been the center of the Calusas' civilization. Except for the occasional pirate of fisherman, Pine Island was then basically uninhabited until 1873,  Those hardy settlers who then arrived, lived off the sea and carved out the paradise that we now enjoy.


Those 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.

Jose 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?

When you look at the Rum Point Inn Bar and Restaurant (previous name of The Waterfront Restaurant and Marina) today (i.e., 1998) it's hard to believe that kids
once attended school in the part that now holds the bar.

But they did, and as the former owner, Whit Whittingham used to laughingly explain, "Where some kids used to learn readin' and writin', they now do their drinkin'."

St. James City's first school was built and opened its doors in March 1887 to about 20 pupils. Built by the developers of St. James-On-The-Gulf, the school flourished until 1894 when the bottom fell out of the development and many people moved away. In May 1896, a fire swept through several homes in St. James-On-The-Gulf, destroying them as well as the school

Some writers mention that a second and even a third school were built at St. James City later on, but no records or recollection of the third school can be found.

By the late 1940's, Pine Island's children were being transported off the island to attend school and the old school building in St. James City was sold and moved again. It ended up beside a newly dug canal along today's Oleander Street, down near Hopkin's Point. There it was turned into a fish camp called the Sea Belle, and run by an Englishman named Leonard
"Whit" Whittingham for many years.

Pine Island's fishing heritage stretches back at least 1,700 years to the Calusa Indians, who lived abundantly off the wealth of seafood in area waters. Commercial fishing has supported generations of island families,  and sports fisherman long ago discovered the abundance of Pine Island waters. Perhaps the best tarpon fishing in all the world lies just north of Bokeelia, in Boca Grande Pass.  Other popular game fish are snook, redfish, trout, grouper, snapper, cobia, sheepshead and many others.  Pine Island is a fisherman's paradise.


Historical information provided by the Pine Island Chamber of Commerce




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