Hilarious Pirate Shirts To Wear at Gasparilla

January 01, 2022

Gasparilla t-shirts clothing

If you’re a die-hard fan of all things pirate, Gasparilla is the event for you. This yearly celebration gives you the one-of-a-kind opportunity to party like a pirate – and dress like one, too.

Every year, residents of Tampa, Florida and visitors from around the globe get together for Gasparilla, a multi-day event that features parades, parties, and a huge procession of boats across the bay. If you’ve never been to Gasparilla, this year is the perfect time to start, especially since the 2021 festival was canceled.

In this post, we’ll fill you in on everything you need to know about Gasparilla. Then, we’ll share some tips for partying in style at this year’s Parade of Pirates. 

After all, pirates were some of the most fashionable folks ever to sail the seven seas. To party like a pirate, you’ll need pirate-worthy attire.

What Is Gasparilla? 

Founded in 1904, Gasparilla Pirate Festival is one of the biggest pirate-themed events in the world. The festival started as a parade in the Tampa Bay area, and it gradually expanded to become a high-profile all-out pirate party. 

Around 300,000 people participate in the festival every year, but several Gasparillas have brought in over a million participants. Next to the Rose Parade and the Macy’s Thanksgiving Day Parade, Gasparilla Pirate Festival is ranked as the third-largest parade in the United States.

What Inspired Gasparilla? 

Gasparilla was inspired by the mythical pirate Jose Gaspar, who is said to have met his end in Tampa Bay in the early 1800s. Sometimes referred to as “The Last of the Great Buccaneers,” Gaspar is a figure shrouded in mystery. Little is known about the details of his life and death. 

Some people think Gaspar may not have existed, and there is no official evidence indicating that he was a real pirate. Bummer.

According to the legends, Gaspar was a true pirate. He’s said to have flirted with a princess named Useppa at one point, only to be shot down. Infuriated, Gaspar cut off Useppa’s head, but he immediately felt terrible about killing her. Filled with regret, he departed to a nearby island, buried Useppa’s headless body, and named the island after her. What a guy.

Another legend about Gaspar says that he was the fiercest pirate in the Gulf of Mexico, constantly capturing ships and building a mountain of loot. Whenever he claimed a ship, he’d threaten to kill its crew unless they joined him in his quest for more ships, blood, and booty—just a normal day in the life of a pirate.

The disappointing reality that Jose Gaspar was probably a myth hasn’t stopped hundreds of thousands of partygoers from flocking to Tampa Bay for Gasparilla every year. These legends about Gaspar inspired the creation of an organization known as Ye Mystic Krewe of Gasparilla, which is now responsible for the annual pirate-themed festivities.

Who Started Gaspirilla?  

The first Gasparilla festival was organized in 1904 by an editor from the Tampa Tribune and the Tampa city director of customs. Editor Louise Francis Dodge and Director of Customs George Hardee wanted to add some of the excitement of New Orleans’ Mardi Gras festival to their own May Day celebration. 

At the time, the May Day parade in Tampa was (according to the locals) pretty damn boring. Louise and George decided to add some pirate-themed excitement to their May celebration to shake things up a bit. Thus, Gasparilla was born. 

The annual Gasparilla parade was held on and off in Tampa throughout the early 20th century. By the 1930s, the Mystic Krewe of Gasparilla organization had its own pirate ship, the aptly namedJose Gaspar, which would sail as part of the parade every year. 

The boat was later replaced with a very expensive new version in the 1950s, which cost the city of Tampa $100,000 to construct. This boat has been featured in nearly every Gasparilla parade since the 50s, aside from a few years when bad weather prevented sailing. 

When Is Gasparilla Held? 

The first Gasparilla parade took place on May 4, 1904, but the date has since been switched. As of 2005, the Gasparilla festival falls on the last Saturday of January.

The only recent Gasparilla to be canceled was the January 2021 festival, which couldn’t happen due to the COVID-19 pandemic. However, the parade is returning for 2022 on the 29th of January in Tampa.

What Do You Do at Gasparilla? 

The primary event at each year’s Gasparilla festival is what’s known as the “invasion.” Countless boats sail through Tampa Bay and into the city during the invasion, crewed by dozens of men and women dressed as pirates. 

These boats are primarily operated by members of Ye Mystic Krewe of Gasparilla, who are responsible for organizing the event. However, just about anyone can sail in the invasion on a private vessel. So, if you own a boat and want to be a pirate this year, go for it!

The invasion’s pivotal moment comes when the Jose Gaspar pirate ship docks outside of the Tampa Bay Convention Center. There, the ship captain confronts the mayor and threatens to take over the city by force. Each mayor of Tampa has participated in the Gasparilla festivities, but different mayors have responded in their own unique ways to the pirate captain’s threats throughout the years. 

After the pirate crew obtains control of Tampa, the pirates kick off a massive victory celebration complete with food, live music, drinks, and much more. The pirates are often accompanied by college marching bands, floats constructed by Tampa businesses, and TV crews. 

Is Gasparilla Kid-Friendly? 

Generally speaking, Gasparilla isn’t an ideal environment for young kids. Alcohol is everywhere, and the crowd of tens of thousands dressed up as pirates gets pretty rowdy. However, if you have youngsters who are obsessed with pirates and want to get them in on the festivities, you need to go to the Children’s Gasparilla Extravaganza.

The kids’ version of the Parade of Pirates is a much tamer celebration, and there’s no alcohol allowed during the parade procession. Like Gasparilla proper, the Children’s Gasparilla Extravaganza draws in tens of thousands of families each year, and many kids participate in the parade itself. 

The Children’s Gasparilla Extravaganza is held yearly on the Saturday before Gasparilla. There are parade events for kids of all ages, including the Preschooler’s Stroll, which features the youngest pirates in wagons and strollers decked out to look like pirate vessels. It’s a blast for kids and parents alike.

What Should You Wear To Gasparilla?


Funny Pirate shirts for gasparilla


If you’re headed to Gasparilla this year, you’ll need some fashionable duds to stand out in the crowd. There are tens of thousands of people at the average Gasparilla celebration, but our collection of pirate-themed apparel will make you turn heads even in a sea of swashbucklers!

Below are some of our favorite selections from our pirate apparel collection. 

1. The “Party Like a Pirate” Hoodie

Party Like a Pirate Gasparilla hoodie

If you want something warm and comfy to wear during Gasparilla, this pirate hoodie is exactly what you need. January in Florida is still January, after all. 

Emblazoned with the iconic skull and crossbones symbol and a memorable mantra written in buccaneer-style font, this hoodie would keep even the most cold-hearted pirate warm on a chilly night at sea.

2. The “Instant Pirate” Sweatshirt 

Instant Pirate Rum Gasparilla Shirt

Pirates love rum – it’s a well-known fact. And what’s not to love about the most popular liquor on the seven seas? Sweet, syrupy, and strong, there’s nothing quite like a bottle of rum. This comfortable pirate sweatshirt lets the world know that all it takes to turn you into a pirate is a little bit of booze. 

3. The “It’s a Pirate’s Life for Me” T-Shirt 


It's a pirate's life for me gasparilla shirt


Yo-ho, yo-ho. 

Featuring a classic catchphrase that instantly brings back memories of a certain pirate-themed blockbuster film franchise, this skull and crossbones shirt will definitely make you stand out at Gasparilla. It’s available in multiple sizes and colors, but we highly recommend getting one in red.

A Treasure Chest of Shirts

Gasparilla is worth a visit if you love pirates (or drinking). You won’t regret taking part in this wild and rowdy festival, even if you have to travel for miles to get there. Every year, people flock from hours away to participate in the Parade of Pirates, and it’s easy to see why – it’s one of the most exciting days of the year in Tampa.

When you head to Gasparilla, make sure to pack your suitcase with plenty of pirate-themed swag. Our pirate apparel collection has everything you need to make this year’s Gasparilla the best one yet.


Shop Gasparilla Shirts


Gasparilla History | What is Gasparilla & Why Do We Celebrate? | 813 Area

Gasparilla Pirate Festival | Gasparilla Pirate Fest

The Legend of Jose Gasparilla | YMKG

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