The Beautiful Florida Island Made Famous by a Fake Pirate

Captiva Island, Florida

The Spanish pirate José Gaspar never existed, but his legend gave Captiva Island its name. According to the tale, he kept captured women on this barrier island while running his pirate operation from nearby waters in the early 1800s.

Here’s the full tall tale behind one of this gorgeous Florida beach destination.

The Spanish Naval Officer Who Became a Pirate

José Gaspar was born in Spain in 1756 to a wealthy family, according to popular legend. He joined the Naval Academy in Barcelona at 18 and became a lieutenant by 22.

After Spain lost to British forces in 1783, Gaspar led fellow sailors in taking over his ship. They sailed to Florida and turned to piracy.

This story first appeared in a tourist brochure for Gasparilla Inn in the early 1900s, not in actual historical records from the 1700s.

Creating a Pirate Kingdom in Florida

Gaspar set up his base on Gasparilla Island in Charlotte Harbor around 1783. The many barrier islands hid his operations from passing ships.

From this hideout, he attacked merchant vessels throughout the Gulf of Mexico for 38 years. Men captured during these raids had to join his crew or die.

Gaspar named several islands after himself and his crew members. Despite his supposed decades of attacks, no Spanish or American records mention him.

The Prison Island for Female Captives

Gaspar built a prison on Captiva Island for women taken during raids. This grim purpose gave the island its name, according to local stories.

Captured women faced two choices: marry a pirate or stay prisoner on Captiva Island. Rich women were held for ransom money from their families.

Word spread about the pirate’s island prison, and ships tried to avoid the Charlotte Harbor area. The prison became known throughout the Gulf as a place to fear.

The Spanish Princess Tragedy

In 1801, Gaspar’s pirates captured a Spanish ship traveling from Mexico. Among the passengers was Josefa de Mayorga, daughter of a Spanish Viceroy.

The ship carried Josefa and eleven young noblewomen heading to Spain, along with their valuable dowries. Gaspar fell in love with Josefa at first sight.

He tried to win her with gifts of stolen treasure, but she refused him. His angry crew demanded punishment for her disrespect, and Gaspar beheaded her.

The Headless Ghost of Gaspar’s Princess

Gaspar regretted killing Josefa right away. He took her body to a nearby island for burial but kept her head with him until his own death.

This incomplete burial created ghost stories that still exist today. Fishermen claim to see a headless woman walking the beaches at sunset, searching for her missing head.

The island where Josefa was buried became known as Useppa Island. The name changed over time from ‘Joseffa’ through years of storytelling.

The Hidden Treasure of Captiva

Over 38 years of piracy, Gaspar collected a fortune in gold, silver, and jewels. Stories say he buried much of this wealth on Sanibel Island near Captiva.

People have searched these islands for centuries hoping to find Spanish gold. Many dug through mangroves and beaches following treasure maps and local tales.

No real Gaspar treasures have ever been found. The treasure stories helped early Florida tourism by attracting visitors who hoped to get rich.

The Pirate’s Compassionate Side

Not all Gaspar tales show him as cruel. Some stories reveal moments of kindness from the feared pirate captain.

His first mate Roderigo Lopez missed his love Sanibel in Spain after years at sea. Instead of punishing this feeling, Gaspar gave him a ship to sail home.

Another tale tells of English captive Ann Jeffries who fell in love with crew member Batista Fuentes. Gaspar arranged their marriage and safe passage to England.

The Last Survivor’s Tales

Juan Gomez, a cabin boy captured in 1812, joined Gaspar’s crew at age twelve. He became the last living member of the pirate band.

After Gaspar died, Gomez escaped execution and lived in fishing villages along Florida’s coast. For decades, he told stories about Gaspar’s adventures to anyone who would listen.

He claimed to know where treasure was buried, but his maps led nowhere. Gomez drowned in 1900 while fishing, supposedly at the incredible age of 120.

The Pirate’s Dramatic End

By 1821, Gaspar wanted to retire from piracy. He gathered his crew on Gasparilla Island to split their treasure before going their separate ways.

During this meeting, they spotted what looked like an easy target – a British merchant ship. They couldn’t resist one final raid and sailed out to attack.

As they got close, the ship revealed itself as the USS Enterprise, an American warship hunting pirates. Facing capture, Gaspar wrapped anchor chains around himself and jumped into the sea.

The Birth of a Florida Legend

The Gaspar legend grew in the late 1800s through promotional materials from the Charlotte Harbor and Northern Railroad Company. These pamphlets attracted tourists to Florida’s coast.

Tampa’s wealthy residents created Ye Mystic Krewe of Gasparilla in 1904, starting pirate festivals that still happen today. The annual event features fake pirate invasions of Tampa Bay.

The author of the original Gasparilla Inn brochure later admitted making up the whole story. Despite this, the legend became part of Florida’s identity.

Visiting Captiva Island

You can reach Captiva Island via the Sanibel Causeway from Fort Myers, followed by Captiva Drive.

The island is open year-round with public beaches like Captiva Beach and Alison Hagerup Beach Park (Captiva Beach Park). Popular activities include shelling at low tide, dolphin cruises with Captiva Cruises, kayaking through mangroves, and fishing charters.

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