How A Pirate Festival Made Me Crush On A City

Greetings from Tampa! I write from Lazydays, where Nellie’s windshield is being replaced; more on that in another installment.

It’s Tuesday, and I am still recovering from Saturday’s Gasparilla, Tampa’s months-long community celebration which includes a Pirate Invasion and Parade of Pirates on the last Saturday in January.

I returned to Tampa this year specifically for Gasparilla. Last winter, visiting Tampa for two weeks, I first learned about it; I had never heard of it before. I was intrigued by the notion of a city-wide celebration not historically tied to an equinox (like Easter) or a solstice (like May Day) or a religious rite (like Mardis Gras). While Tampa is adjacent to many activities, on my last visit I didn’t find the town to have much personality or soul (“In many ways, Tampa still does not have that sense of place. The downtown core feels more like a collection of buildings than a community.”), and I wondered if Gasparilla might change that impression. It did.

A Pirate Origin Story

Those clever Tampa luminaries – they fashioned a civic event out of whole cloth, shamelessly borrowing from myth, marketing, and Mardi Gras celebrations in sister cities. In 1904 the Tampa Director of Customs and the Tampa Tribune Society Editor conceived a festival inspired by Jose Gaspar, a mythical pirate who allegedly plundered the waters of western Florida in the late 1700’s/early 1800’s. There is no written history of Gaspar, in Spain or Florida, until 1900, when he appeared in a travel brochure for Henry Plant’s new railroad to the Florida west coast.


Similar to Mardis Gras, Tampa businessmen and civic leaders formed a krewe, or social club, to plan the festival. Ye Mystic Krewe of Gasparilla, formed in 1904, is still in existence today, and it is the YMKG pirates who “invade” Tampa aboard the Jose Gasparilla, a pirate ship festooned with flags which makes its way down the Hillsborough River to downtown Tampa. They make land and meet with Tampa’s mayor, who gives them the key to the city. The parade of pirates ensues, when they share their booty with the city. That booty? Beads. Lots and lots of beads.

From Wikipedia:

Over the years Gasparilla has burgeoned into a three-month-long celebration. There is a music festival, art show, marathon, and an alcohol-free children’s parade. The other event which intrigues me is the Knight Parade in Ybor City, which is two weeks from now. Alas, I will already be at Mardi Gras in New Orleans. The Knight Parade is sometimes mislabeled the night parade, because it occurs at nighttime and features illuminated floats. Since the 1970’s the parade has been sponsored by The Krewe of the Knights of Sant’ Yago, dedicated to preserving Tampa’s Latin heritage.

Gearing Up For Gasparilla

For pirate gear I headed to South Tampa Trading Company In Tampa, and Land of Make Believe in Clearwater, both of which were disappointments; South Tampa Trading Company has lots of rhinestones and skull stuff and costumes for itty bitty women. When I asked for recommendations for other costume shops in the area, I was told I could Google it. Really? What is this thing called Google of whence you speak? So much for a local recommendation!

Land of Make Believe is really more of a all-purpose costume shop with a little bit of pirate stuff, and they didn’t open on time or answer their phone. Next!

If you are looking for a high-quality and authentic pirate costume, go see Tiger Lee and the other rogues and rapscallions at Pirate Fashions. They take their pirating seriously. For example, when you enter the warehouse-style store you must ring the bell and ask permission to come aboard. (While I was there a new customer at the door looked perplexed and put out by the tradition, whining about having a plane to catch. Lady, if you can’t handle this little bit of harmless frivolity, you have no business buying a pirate costume!)

There are so many reasons to love Pirate Fashions. They are plus-size friendly. They have just as much gear for women and men, and the women’s costumes are not all T&A and fishnets. They make many accoutrements in house, including hats and leather goods. They have a buyer rewards program, and you should sign up because you’ll spend a lot of money. And, for a single gal like me, on the day of Gasparilla they will cinch you into your corset!

The Pups Go To Camp

I couldn’t believe my luck. Directly next door to Pirate Fashions was Camp Bow Wow, a doggy daycare and boarding facility. On the Monday prior to Gasparilla I took Rocket and Pinkie in for their temperament tests. As usual, Rocket was the goodwill ambassador, and Pinkie just wanted to hang out with the humans. Nevertheless, they both passed with flying colors, and they would have a place to hang out on Gasparilla day.


On Gasparilla morning I dropped off the pups at Camp Bow Wow, then went next door to get trussed up into the corset. Corsets are oddly comforting; they suck everything in and force perfect posture.

Then, I got behind the wheel to drive. Not easy! Other not easy things to do in a corset: sitting in general, and going to the bathroom, which I do a lot. Oiy!

This year’s Gasparilla Invasion and Parade of Pirates coincided with the National Hockey League All-Star game weekend festivities. Over a half million people were expected in downtown Tampa. News reports optimistically predicted “organized mayhem.” To beat the traffic I parked in Ybor City, the national historic neighborhood where Tampa cigars have been rolled for over a century. A trolley runs from Ybor Centro directly to the Tampa Convention Center, where I had a ticket for brunch.

You might be wondering how a Crohn’s person like me could participate in Gasparilla, and, like most things, it just takes a little ingenuity … and money. The brunch ticket at the Tampa Convention Center came with bathroom facilities and the best view of the invasion money can buy. For the parade, my bleacher seat ticket included nearby porta-potties.

The numerous and varied Gasparilla activities afford everyone an opportunity to participate at their comfort level. Likewise, on the day of the invasion and parade, you can choose your level of pirate attire, from none to just-stepped-off-the-set of “Pirates of the Caribbean.” I had such fun asking strangers to pose for photographs, and they were all more than happy to show off their outfits.

This fellow was visiting Gasparilla for the first time from New York, and he is a paid pirate at other festivals. Great Barbarossa!

The YMKG krewe arrived right on time, to the on-the-nose tune “The Boys are Back in Town.” The Stanley Cup was even on board, in its own little life jacket.

(Photo: districtflooring on Instagram)

I had the perfect vantage point snap some photos of the invasion.

The parade felt very much like Mardi Gras, except all the floats were pirate or sea-themed.

Yo Ho, Yo Ho, A Pirate’s Life For Me

As I drove around Tampa for costumes and to pick up tickets, the Gasparilla buzz was palpable. People were in a jovial mood. Almost every home was festooned with a pirate flag and Gasparilla-themed door wreath. That all-male, all-white krewe is now integrated, and there are many krewes representing many types and groups of people; they fundraise and organize events all year long for charity.

On Gasparilla Day, as I walked in Ybor city, a homeless man called out, “You make a great looking wench!“ I thanked him and he said, “And I love I can say that to you today and not be offensive! Today only though!” It made me smile.

People asked to take my photo. Strangers took photos for each other.

I read there were a total of 39 arrests on land and water on Saturday, all misdemeanor stuff.

Tampa knows how to throw a great party, for absolutely no reason at all, but who really needs a reason?