The most notorious and successful pirate was Jose Gaspar, better known as Gasparilla. His methods were black and bloody, and he stands out among all the pirates who used Florida to bury their wealth. Leaving Spain at an early age, he sailed to the west coast of Florida. He soon picked a good spot in Charlotte Harbor, and b...egan to build his pirate kingdom. His headquarters were at Boca Grande, on what is today known as Gasparilla Island. In the following years, he accumulated a board estimated at $30,000,000. It is said that he and his brother buried all of his money on the islands in and around Charlotte Harbor. In all, he buried 13 casks and chests of treasure in the vicinity of his headquarters. His men, who numbered in the hundreds, also buried their smaller caches on these islands.
All had been going along fine for Gasparilla until the year 1821. The American Government then decided to get into the act and sent a Navy squadron to end his career. One day Gasparilla prepared to attack a merchantman, but to his surprise, it turned out to be a United States man-of-war. When he finally realized that it was a warship, it was too late. The notorious pirate then committed suicide by wrapping a heavy chain around himself and jumping over the side. His ship soon followed him to the watery depths. The ship contained $1,000,000 in assorted treasure, and should be there today. Charlotte Harbor is an ideal spot to go treasure hunting. Just pick any island and start digging, because Gasparilla’s loot is buried on many of them.
Another pirate who made his headquarters near Charlotte Harbor was Black Caesar. He was a former slave who escaped to the west coast of Florida. Soon afterwards he became leader of the pirates and built his base on Sanibel Island. It is said that he captured a Spanish galleon off Cuba, and brought it back to his stronghold. Among other things on the galleon were 26 tons of silver, which he quickly buried. This enormous hoard is supposedly on or near Sanibel Island.
The major mystery of Gasparilla’s life still remains, though. What happened to the treasure the pirates were dividing? Legends say there were twenty huge chests spilling over with gold, jewels and other treasure. The chests were on the beach when the merchant ship was spotted, and it is said Gasparilla left ten of his most trusted men with them when he sailed off. Here things get even more murky… The ten pirates obviously saw the pirate ship go down. Supposedly they loaded th...e chests into a boat and sailed up the Peace River to hide the treasure.
In some stories, they ended up at a place called Spanish Homestead. Here they bribed the owner with some of the treasure so she would point any pursuers in the wrong direction. The ten spent the next day burying the chests in different locations along the Peace River. They then burned their boat and disappeared.
Part of the legend apparently was true as $300,000 in gold coins was found years later near Spanish Homestead. However, none of the remainder of Jose Gaspar’s $30 million treasure has ever been recovered!