Gasparilla 101: What's the story behind Gasparilla?

By Felix R. Albuerne, Digital Media Producer
Last Updated: Friday, January 20, 2017, 4:21 PM EST

So you’re new to the Tampa Bay area and you’ve heard people talking about Gasparilla. They may be talking about dressing up as pirates or a big ship sailing into the bay and a huge party or just a lot of drinking. They may even be talking about some kind of takeover of the city.

Are they serious? Well, sort of. Here’s everything you should know about one of Tampa’s oldest and most well-known traditions – the Gasparilla Pirate Fest!

What’s the story behind Gasparilla?

Legend tells us that the notorious pirate José Gaspar, also known by his nickname, Gasparilla, based his nefarious operations out of an island off the coasts of Lee and Charlotte Counties.

From there, he raided and plundered shipping lanes and towns along the Gulf Coast, doing what pirates are wont to do -- yo ho, yo ho, a pirate’s life for him and all that good stuff. According to, he was credited with capturing over 400 ships between 1789 and 1821, and supposedly he buried his enormous treasure on the island he called home, known in modern times as  --- surprise! – Gasparilla Island.

The legends also say Gasparilla met his end after attempting one last capture. He thought he was going after a British trader, but he realized too late the ship he was attacking was the United States Navy pirate hunting schooner U.S.S. Enterprise.

The Enterprise tore Gaspar’s ship to shreds with cannon fire, but the pirate would not be taken alive. Instead, he wrapped a heavy chain around himself and leaped from the bow of his ship into the murky depths of the ocean.

None of Gasparilla’s treasure was ever recovered.

So what exactly is the Gasparilla Pirate Fest?

The He Mystic Krewe of Gasparilla float at the festival, 2016. (Virginia Johnson, Staff)

The Gasparilla Pirate Fest celebrates the colorful life of Gasparilla, the “Last Buccaneer,” and the city’s ties to the legend.

Every year, the world’s only remaining full-operational pirate ship, the José Gasparilla, leads a flotilla of ship carrying 750 “pirates” into Tampa Bay, firing its cannons and demanding the city’s surrender.

And every year, the city surrenders. The pirates then take to the streets in a huge celebratory parade, with floats and pirate krewes taking over the streets of Downtown Tampa. The party continues on through the night with the Gasparilla Street Festival, featuring food, live music, and entertainment.

The Gasparilla Parade of Pirates is recognized as the third largest parade in the United States.

The full slate of Gasparilla-themed events actually begins in late January, and ends in March.

Does everyone dress up as a pirate for Gasparilla?

Pirate flags flutter in the wind on the Krewe of Hillsborough's parade float, January 24, 2016. Everyone lined up for fun despite the wind. (Virginia Johnson, staff)

No, not everyone dresses up, but getting into the spirit of things is certainly encouraged. Consider it the one occasion on the calendar in Tampa Bay when you can put on an eye-patch and answer everyone who speaks to you with “Arrrrr!”

What’s not to love about that?