10 Funny Shirts for Gasparilla Pirate Fest

December 15, 2022

10 Funny Shirts for Gasparilla Pirate Fest

If you're from Tampa Bay, you're probably familiar with Gasparilla. Whether you're hitting the parade with friends or going alone, please make the most of it with some of the funniest Gasparilla apparel ever! But let's educate those clueless about what this Gasparilla pirate fest means.

Gasparilla Apparel: What Is Gasparilla?

Look, we're only going to explain it once - It's a rad parade held annually to commemorate the invasion of the legendary pirate Jose Gaspar, also known as Gasparilla. Into Florida.

Gasparilla Apparel: How Did It Come To Be?

According to folklore, Gaspar invaded the West Coast Waters in Spanish Florida Tampa, precisely, in 1911. But he had already done the first invasion on horseback in 1904. Captain Jose Gaspar left a lot of plundering in his wake. That’s why for the past 100 years or thereabouts, Tampa Bay has seen a sh** ton of plundering yearly by a bunch of … (are there kids here?)

Not that this information is helpful or makes the festival more kick-ass (literally) than it already is. l mean, there's drinking - lots of it! Plus, we get to rock our Gasparilla apparel. We'll teach you how to turn up like a proper pirate. Ready? Drink up. It's intense…

1. Initiation Into the Pirate Life

Jolly Roger + It's A Pirate's Life For Me T-Shirt

You must be correctly sworn in. The requirements are simple: hold your liquor and declare with your right hand, "It's the pirate life for me." Also, you must have pirate apparel with that inscription. You can get it here, though.

2. Learn to Party Like a Pirate

 Tank Tops + Party Like A Pirate

Hear, hear! Do not attend the Gasparilla pirate fest if you're a party pooper! Be cool, man. Get lost in the fun, or get out! Anyhoo, what else do pirates do asides from looting, throwing stupid jokes around, and partying? The best life to live.

3. Surrender the Booty

Pirate Shirt + Gasparilla T-Shirt

Does Jack Sparrow’s face come to mind when you think of pirates pirating? Aye! Nobody teaches us better except Jose Gaspar himself. So, get your groove on in this pirate shirt. If you don’t do anything fun, this should be a great way to prove you’re one of the krewes. Tell those lazy drinkers to surrender the booty. Just don’t expect anything, and be ready for everything. It’s your fellow pirates, anyway.

4. Be a Scallywag!

Gasparilla apparel + Gasparilla Island

Oh dear, you thought the pirate fest was for proper people? Look around you! Everyone who will show up is a major idiot. No offense. Get in line and just be a proper scallywag now. That’s pirate 101.

Don't bother going if you want to look down your nose at everyone. It’s just a bit of fun and foolery. Enjoy it. Here’s a pirate t-shirt for it, too.

5. Instant Pirate, Just Add Rum!

Gasparilla Rock + Gasparilla Store

Do you know how you make instant noodles? Yup, that’s how you can instantly make yourself or your buddy a pirate.

Since y’all are attending something as crazy as the Gasparilla parade, going all the way to Tampa Bay, nothing is left. (facepalm). Just add rum, and bam! Instant Pirate.

So, grab a pirate costume for you and your crazy friends. You can throw in long sleeve t-shirts … or not… Feel free to even go with your own pirate skull. Just don’t forget the rum!

6. Catsparilla for the Kitty Lovers!

Gasparilla Apparel + Gasparilla Jacket

It’s weird enough that you have an intense obsession with cats. Yea, we know about your cat whiskers collection, the shirts, and that book with your cat’s paw prints.

Yes, in your version, Jose Gaspar was Jose Catspar, a freaking cat!

Perhaps you can hide your boatload of crazy on the Gasparilla pirate ship. Or should we say catsparilla? Tone it down with this simple Gasparilla apparel. Lord knows you need to put the blend in.

7. Why Is the Rum Gone?

Custom college apparel

Rum, rum, rum your boat, gently down the … what now? Yea, tell us, captain crazy.

Expect silly questions like this at the parade. When everyone is wasted, which will happen shortly after the fest kicks off, don’t be shocked to hear your buddies slurring and asking why the rum is gone. If you have no intention of making any drunken slurs, get this t-shirt from us. Be a good captain and get one for your crew members too.

8. I’m the Reason the Rum Is Gone


Imagine the shock when the quiet friend everyone ignores raises his hands, eyes closed in drunken reverie, and he goes, “Yea, I’m the reason the rum is gone,” And everyone looks at him like he’s Jack Sparrow who’s sleeping with the merchant’s wife. Lol.

We don’t want to be part of that crowd. You don’t want to be that friend, either. What’s the answer? One of these good old Gasparilla shirts.

You could even be the bold one. Just remember that Jack Sparrow always gets the crap beaten out of him.

Okay, this is getting too wild. Time out! Just appease everyone in your krewe with free Gasparilla apparel.

9. Save Water, Drink Rum


It sounds silly, but in the legends of the pirates and the sailors, it was easier to get rum than clean water. In fact, the rum helped in purifying the water. Then, the sailors and pirates would keep the little clean water and opt for rum.

But I bet you thought it was just for the sake of being silly. Surprise your crew with the backstory of this inscription. Be sure to hand them out as little pirate gifts.

10. Get Ready to Be Ship-Faced

Ship-Faced Shirt

There’s no way you can join the looting and plundering while sober. In fact, it defeats the purpose of the entire operation.

To truly be a pirate, get ready to be ship-faced. Don’t look at us funny. You decided to join a bunch of freebooters. We’re just here to prepare you, mind, soul, and shirt. So, take this Ship-faced shirt along.

You’ll need it when you’re getting too wasted to express yourself. Or you can wear it and pretend. No one has to know, right? Great.

Away with the loot! As long as our Gasparilla apparel isn't part of it. Enjoy your Gasparilla pirate fest. That’s too many Gasparillas in one sentence. Help! I think I’m a pirate now.


Gasparilla Collection

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