Gasparilla: A Pirate’s Tale

Feb 5, 2019

Gasparilla is an annual pirate festival held in Tampa. Chelsea covered this event two years ago. Now ye be hearing it from the Captain!

For me, the Gasparilla experience can be defined by two things – who you go with, and what you make of it. The Gasparilla crew you go with makes or breaks the event, and I highly recommend getting into the spirit of the thing with food, drink, and dress. Costuming is an awful lot of fun, and gets quite a lot of compliments, notice, and picture requests along the parade route. Having a crew of your own to attend with, from a gathering of friends to a costuming troupe of piratical enthusiasts, makes the time investment much more with it. And of course, having alcohol on hand to share with said friends is an excellent way to help dull the passage of that time, as you wait for drunken ‘pirates’ to sail into shore, disembark from their vessel, threaten the local heads of government, and finally get their parade rolling.

On it’s own, the event is fairly straightforward – a very long parade that starts at a variable time, and takes most of the afternoon and early evening to roll through the streets of Tampa Bay. Don’t expect to simply show up, plunk down next to the parade route, and leave within the hour. It’s a ‘day’s worth of entertainment. Sometimes the crowd can be as entertaining as the parade proper! The floats themselves can be very impressive, but do take heed that some are hit and miss. While many floats are quite over the top with the grandeur of entire pirate ships or fortresses, others offer a much simpler presentation that, at times, is little more than a truck pulling a decorated trailer.
 
This Gasparilla, we started the ‘event’ early ourselves by having an in-costume and themed pre-party at my best-mate Robert’s house. You might remember him from our Pirate Proposal last Halloween. It was a close, intimate affair with tobacco smoke and free-flowing grog spilling from leather-bound cups as we sat around a fire pit on his property. Sea-shanties played from outdoor Bluetooth speakers, piped in from a playlist Robert had hand-picked. Rum, whiskey, and properly mixed grog were poured and consumed in abundance while we cooked dinner on the grill and over the fires. At some point, the sea-shanties became a sing-along, and there was much drunken debauchery and celebration before the hour grew late and we were reminded we had to be awake for the drive to Tampa the following morning.

Hitting the ‘Invasion’ portion of Gasparilla doesn’t mean you miss out on the parade itself – which is often the highlight for many. When the crew of that massive pirate ship sails into Tampa’s harbor every Gasparilla, the crew have made it a bit of a tradition in handing out what is lovingly known as “swag.” If you want to try to score some of the more rare treasures handed out during the event, the disembarkation of the pirate crew is not to be missed. From simple things like sponsored strings of beads, flashing skull pendants, eye-patches marked with the official logo and year, to the much more interesting doubloons – golden and silver coins emblazoned with the face of the king and queen of that year’s event, to coins marked with the date or stamped with a pirate ship and the likeness of one Jose Gaspar, the folklore-inspired Pirate of Gasparilla fame. That’s not to say these bits of shine aren’t available to be thrown out from the floats during the Parade itself, but disembarkation is when it’s far easier to get your grubby, piratical hands on them.

Having lived in New Orleans for a few years at one point, I’ve seen Mardi Gras recreated in many forms. Here in Florida, Universal Studios has its own version of it, which often has floats direct from the New Orleans float artists’ hands! Comparing Gasparilla to Mardi Gras is fairly easy, but does it a bit of a disservice by ignoring the over-the-top piracy aspect that the festival in Tampa has going for it!  While you wait for the parade, it’s best to have something to pass the time – for many, it’s the act of day-drinking, as most of the laws are relaxed concerning coolers and open containers of alcohol.

However, Robert and I had brought an entirely different sort of distraction (although, like right and proper pirates, we had brought quite a haul of rum, beer, and grog.) We played an ancient nautical game called “Shut the Box”, which is sold many places but is also a game that’s relatively easy to build yourself with basic supplies. While I won’t go into detail concerning how to build your own setup or how to play the game (look for that DIY coming in a future post), suffice it to say it’s a simple game that involves two six-sided dice and a row of numbers. Rolling the dice and turning the numbers face-down is all there is to it, but once you add some shiny golden coins, or in our case grimy, sea-salt encrusted doubloons, it takes on a much more competitive edge. We must have played dozens of hands, but the constant back-and-forth of the coins kept it fun. Also, having the crowd at the parade watching two pirates throw clinking coin into a box while swigging from tankards and smoking pipes resulted in a lot of comments and photographs, and we were interrupted fairly regularly to talk about our appearance, our pistols and swords, and the game itself.

As the parade rolled, it was the usual loud-music and debauched ensemble that happens when people who’ve been drinking all day wait for a parade that consists of thrown beads from floats. It can get a little over-the-top, and I can’t say it’s exactly the most ‘family friendly’ of events in Florida, but it certainly doesn’t reach the lofty heights of Mardi Gras, either. Buyer beware, mileage may vary, take it with a grain of salt, but it’s not too bad. I’d be very hesitant to take any children under sixteen or so, however.
 
 

Following the parade, we made our way to an Airbnb that we had arranged in Ybor city. While some of our number went out for more hi-jinx, the entire city essentially sacked by costumed fun-seekers don up as pirates, I chose to sit in and put my boots up and enjoy a chance to rest.

Cost: The event itself is free.
Value: It is what you make it.
Duration: ALL DAY!
Add Ons: Drink up me hearties, yo ho!

Moving to Orlando in 2013 to join the Disney College Program was the start of the Great Florida Adventure for Chelsea and her best friend Duffy Bear. Now they spend their days exploring all there is to do in the Orlando area and seeing what adventures life where the rest of the world vacations brings.

Author Chelsea leaning on a fence at Disney.

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