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Gasparilla: Time to Let yer Jolly Roger Flag Fly


This year, National Talk Like a Pirate Day falls on September 19. But here in Tampa, we start our Jack Sparrow speak-and-swagger much earlier – right after the New Year. That’s when our annual Gasparilla season begins, and for three months we get to dress, behave, and party like pirates. If you’ve never put on a Blackbeard outfit or experienced the grog-friendly hijinks of Gasparilla, here’s a primer for all you scallywags.

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Aargh! But first, a little history


Gasparilla is named after a mythic pirate named Jose Gaspar, aka “the last buccaneer,” who plunged and pillaged Florida’s waters from the late 18th to early 19th centuries. It’s been said that when he died, he left a trove of buried treasure somewhere along the coast of Florida.

Fortunately, Gaspar’s legacy did not get buried with his bounty of gold. In 1904, the Society Editor of the local newspaper and the city’s Customs Director merged the pirate’s folklore with elements of Mardi Gras – and Tampa’s “Gasparilla Invasion” was born. Today, it’s known as Gasparilla Pirate Fest.

Toss me some beads, mateys! 

Ye Mystic Krewe of Gasparilla was the first private club established, and members have been the exclusive organizers of Pirate Fest ever since. The Krewe boards a fully-rigged ship and sails into downtown Tampa, guns and canons afire, re-enacting Gaspar’s legendary invasion. Following is a flotilla of other Krewes and boats. The parade takes place on Tampa’s famous Bayshore Boulevard, with hundreds of pirates on floats tossing beads and souvenirs to screaming onlookers. The typically raucous celebration draws about 300,000 paradegoers, but in 2018, the NHL All-Star weekend  in downtown Tampa coincided with Pirate Fest, boosting attendance even more.

Initially, Gasparilla was held on the first Monday of February, and was an official holiday in Tampa, with schools and businesses closed. It was moved to the first Saturday in February in 1988, then to the last Saturday in January in 2005.

In total, there are three parades during Gasparilla season. The Children’s Parade, also on Bayshore Boulevard, is the official kickoff to Gasparilla, and occurs a week before Pirate Fest. The third, Sant’ Yago Knight Parade, takes place a week after Pirate Fest, and occurs in Tampa’s historic Latin district, Ybor City. Three parades, hundreds of thousands of beads for the tossing and grabbing. If you walk away empty-handed, it’s your own fault. Aargh! 


Avast ye! There’s more fun to be had

 Yo ho ho! Think it’s all about parades? Ah, shiver me timbers and walk the plank! There are plenty of other ways to get your pirate on. 

Gasparilla Distance Classic

In February, runners of every level take to the streets of Bayshore and downtown Tampa at this global event that started in 1978. From 15k, 8k, 5K, half marathon, walks, stroller races, and other challenges, athletes run for booty – and their booties off – to benefit charitable organizations. 

Gasparilla Festival of the Arts

Since 1970, Gasparilla Festival of the Arts has been one of the most sought-after competitions by artists and one of the toughest to get accepted. Held outdoors in early March at Curtis Hixon Park, along Riverwalk and the Hillsborough River, the event attracts hundreds of thousands of fine art enthusiasts from around the world. Even better? It’s free.


Gasparilla Music Festival

Only in its sixth year, the Gasparilla Music Festival in mid-March showcases both local and national acts on four stages and a drool-worthy lineup of Tampa’s most popular eateries. Held over two days in mid-March in downtown Tampa, the festival is a must-attend for any music lover. 

Gasparilla International Film Festival

Gasparilla season comes to a close in March –  with a bang and applause – at this international film festival, held at various locations around Tampa Bay. With the intent to inspire and support the local film industry, GIFF is a non-profit organization that features events year-round. 

Aye! Aye! So, there you have it, me hearties. If you ever find yourself in Tampa right after the holidays, surrender to the legacy of Jose Gaspar. Put on yer corsets, britches, boots, feathered hats, and eye patches, and brush up on yer slurry speech. For one unforgettable weekend – or season – it’s a pirate’s life for you.