There’s no place on earth like Tampa Bay. Tampa may get overshadowed by the nightlife of Miami and the mouse ears of Orlando, but the truth is Tampa is Florida’s hidden gem. With incredible beaches, a dominant sports scene (they don’t call it Champa Bay for nothing), and a thriving arts and music culture, Tampa is quickly climbing to the top of people’s want-to-go-to vacation list.
If you’re planning a trip to Tampa soon, there’s no better time to visit than Gasparilla season. Steeped in tradition, Gasparilla is an annual pirate invasion that’s been thrilling Tampa Bay locals for well over a hundred years. As the festival has grown, it’s become a multi-event affair, with the entire city rallying around to celebrate. With music, art, film, and fun to be had, Gasparilla exemplifies the best of what Tampa Bay has to offer.
This is your guide to the annual pirate invasion.
First, a quick history lesson. Gasparilla gets its name from a pirate who terrorized the western Florida coastline during the late 18th and 19th centuries. José Gaspar was his name, and thievery was his game.
As legend has it, Gaspar amassed a still-not-found treasure over decades of pirating. In 1821, he and his merry crew were ready to part ways and enjoy their riches but decided to seize one last ship. You know, for old times sake. Unbeknownst to them, their target ship was actually a US Navy warship in disguise. After a bloody battle, Gaspar allegedly tied an anchor around his waist and jumped into the water to avoid capture. That is the legend of the Gasparilla.
Did it actually happen? Historians can’t exactly agree on that topic. Census data doesn’t include a José Gaspar living at that time and pulling large-scale piracy. Much of the lore around the pirate is based on a 1935 account of his exploits, written by Edwin D. Lambright of the Tampa Morning Tribune. Much of this writing was debunked as fiction in 1980, but that doesn’t stop Tampa from celebrating the man and the myth.
Regardless of whether or not José Gaspar was a real person, his spirit is alive and well every year during Gasparilla season in Tampa Bay. Since 1904 the city has been celebrating its pirate roots in an increasingly large parade and party that now spans several months.
Are you looking to get into the festivities? This is how to do Gasparilla like a Tampa local. That is, after you’ve checked out our Tampa Bay Always on Vacation tee.
The pirate invasion is the central event of Gasparilla season.
That’s right, at the end of January, pirates take over the city of Tampa. Ye Mystic Krewe of Gasparilla creeps into the bay, where they’re met with a flotilla of Tampa locals who attempt to defend the city. Long story short, the pirates win every time, and the Jose Gasparilla ship leads a parade of pirate friends all the way to the Tampa Convention Center, where the mayor is forced to hand over the keys to the city. Ridiculous? Maybe. We’d call it ridiculously fun.
There are many spots on the water to watch the parade go by. The Riverwalk is sure to be packed with people looking to check out the invasion and catch some booty from the ships. Pirates toss beads to spectators, so get your hands up in the air as they pass by. You’ll have more than enough opportunity as more than 1,300 boats participate. With 300,000 descended upon downtown Tampa to watch the festivities, you’ll be in great company.
For bonus fun, try to find a local with access to a motorboat so you can watch the invasion from the water. Fair warning, the pirate invasion is an all-out fiesta with lots of partying. Get ready for some serious fun, and remember to stay hydrated.
Ybor City is the ancestral home for Tampa Bay’s thriving culture. It was once the cigar capital of the world, led by a wave of Cuban immigrants that still shape Tampa’s local music and cuisine. Today, Ybor City is the HQ for Tampa’s arts and nightlife scene.
Usually taking place a few weeks after the pirate invasion, the Knight Parade in Ybor City is a spectacle worth seeing, lighting up the night sky with colorful and luminous floats. The parade has been hosted by the Knights of Sant’Yago since 1974 and celebrates the rich history of Latin Americans in Tampa Bay.
The parade is always hosted by a king, El Ray, and his queen, La Reina, who leads a pack of pirates through the streets of Ybor. And yes, there are more beads to be collected here.
This Sant’Yago Knight Parade is a great opportunity to visit Ybor and get to know some of the history behind the Tampa we know today.
Gasparilla is about more than just parades. It really encompasses over a month’s worth of celebrating and special events, which also includes a series of running races called the Gasparilla Distance Classic.
There’s a half marathon, a 15k, an 8k, and a 5k race, in addition to a number of children’s fun runs and other team events and challenges. There’s really no better way to get a sense of the spirit of a city than to run through its various neighborhoods.
If you’re anywhere from a casual runner to a serious runner, you should definitely check out the options to join in a race. More than just a workout, the Distance Classic is responsible for more than $3.9 million in donations to charitable youth organizations across the Tampa Bay area.
Getting some endorphins for a good cause? That’s what we call a win-win.
If running is not really your thing, there’s plenty more to do during the Gasparilla season that doesn’t include lacing up sneakers.
Tampa is home to a huge arts scene — the Tampa Bay Riverwalk includes gorgeous murals and street art worth checking out — and every year, it comes together for the Festival of the Arts at the Julian B. Lane Riverfront Park.
Hundreds of artists from all over the world participate in the festival, from painters to sculptors to woodworkers, all vying for the chance to win the Raymond James Best of Show award. Spectators can explore a sea of tents displaying artwork as well as great live music and food stands.
On the topic of music, Gasparilla season also includes a concert festival. The three-day affair features diverse local Tampa acts as well as nationally recognized headliners. Similar to the arts festival, it also includes some classic Tampa Bay food vendors that’ll give you the authentic Tampa experience.
Last but not least is the Gasparilla International Film Festival. Since 2007, the organization has hosted a competition, inviting up-and-coming narrative and documentary filmmakers to screen work and compete for the grand jury prizes.
Big names and emerging talent alike come through for the competition. Attendees can enjoy screenings of the films and talks with the directors and casts. Movies and events are held all over the city, so if you’re a film buff, this is an excellent opportunity to see the many theaters Tampa has to offer.
Where else in the world can a pirate invasion and a prestigious film festival go hand in hand? That’s just one reason we love Tampa Bay. If you’re going to the city during Gasparilla season, which generally spans the first three months of the year, make sure you enjoy everything the city has to offer. From the arts, music, and film festivals to the rollicking parades and parties, José Gaspar, real or fictional, made a lasting impact on Tampa Bay.
If you want to do Gasparilla like a local, make sure to catch the pirate invasion from the water, light up the night in Ybor City with the Knights, start training to run miles around the city with the pirates, and buy tickets to see local arts, music, and films. Bonus points if you actually pack a pirate costume.
You know what else you should pack? Anything from our Tampa Bay collection, including t-shirts that feature the city’s most beloved teams of the past, inside jokes, and, of course, the Cuban sandwich.