Gasparilla's Headless Princess

Jose Gaspar

Arrgh! September 19th is International Talk Like a Pirate Day! My accent is a little off and my wench dress is at the cleaners...so I think I'll just celebrate with some pirate ghost stories! The legends and lore of America's pirates are steeped with superstition and supernatural elements, and many of our most well-known bearded bullies of the sea are said to still be hanging around in spirit form. Whether they are still guarding their buried treasure, seeking to exact revenge on those who did them wrong, or simply being punished for a life of misdeeds, these pirate ghosts and the ghosts of their hapless victims make up a huge chunk of our country's ghost lore.

While pirate ghosts can be found in many coastal areas, (and apparently in Ohio, as well!), this particular tale comes from Gasparilla Island in Florida, part of a chain of Gulf Coast barrier islands. For almost 200 years, visitors to the island, which for over a century has been home to the Boca Grande Lighthouse, have claimed to see what appears to be a headless woman roaming the beaches.

Like most pirate ghost tales, this story also seems to be steeped more in folklore than in history, with no real historical evidence to back up the claims or even prove that the main characters even existed. So then who is this strange, headless apparition? As the legends go, the famed Spanish pirate Jose Gaspar, better known as Gasparilla, used the island as his home base of operations throughout the late 18th century and into the early 19th century. He is even said to have buried treasure somewhere on the island near where the lighthouse now stands. Unfortunately, material treasure wasn't the only thing Gaspar sought to make his own---he also had a thing for collecting beautiful women, which he held on a nearby island now known as Captiva Island.

One of the women he captured was allegedly a Spanish princess known as Josefa. Josefa was a great beauty, and Gasparilla wanted nothing more than to make her his own. However, the more he attempted to win her over, the harder she spurned him, until finally one day, she spat in his face. In a fit of rage, Gasparilla grabbed his sword from his side and Josefa's head off. Distraught over killing his beloved Josefa, Gasparilla took her body to his own island to bury it.  However, legend states that he only buried her BODY. He apparently kept her head with him until his own death in the 1820s.

Since then, the headless body of the Spanish princess has been spotted on the beaches of Gasparilla Island, looking for her missing head. Some say Gasparilla himself has also been witnessed wandering the beaches. Is he looking for that treasure he buried---or is he looking for his lost love, Josefa, who continues to spurn him even in death?

If you visit the island, don't be too discouraged if you don't see the poor Spanish princess or the love-sick pirate. Just make sure you check out the old lighthouse, which has plenty of ghost stories of its own!

Source: Lighthouse Ghosts, by Norma Elizabeth and Bruce Roberts