Punta Gorda & Pirates: A Strange Love Affair

pirate fest
Every July, Punta Gorda residents and visitors come together to celebrate Pirate Fest.

This year’s fest starts on Friday, July 25, 2014 and runs throughout the weekend at Fishermen’s Village. The event features live music, live mermaids, a pirate ball, a pirate ship, costume contests, treasure hunts, and a fire show.

It’s bound to be a fun weekend. Even if pirates are a strange bunch to celebrate.

After all, the most famous Southwest Florida pirate, José Gaspar, was kind of a jerk. While there are many stories and rumors about Gaspar, the most famous one goes like this:

At age 12, Gaspar joined the Spanish Navy. Over the next few years, he moved up the ranks until he was trusted with some of the crown jewels.

He stole the jewels—possibly for the love of a woman or possibly because he was a jerk. (Historians disagree on the why.) Either way, with crown jewels in hand, he set sail to begin his pirating career around 1783.

By the turn of the century, Gaspar, who by then called himself Gasparilla, had a nice little career of taking over ships, killing all the men, and capturing all the women for his harem. He stored his treasure on Gasparilla Island and his women on Captiva Island.

In 1821, on the cusp of his retirement, Gaspar decided he could capture one more bounty. He and his men went after a ship they thought was a British merchant ship, but turned out to be the USS Enterprise, a US navy ship on a mission to eradicate the Gulf Coast pirate problem.

The USS Enterprise attacked. Gaspar realized he wasn’t going to win this battle. Instead of letting the enemy kill him, Gaspar tied the anchor to his waist and jumped from the ship.

So, Why Do We Celebrate Pirates?

I’ve spent over thirty years studying the Punta Gorda resident in its natural habitat. And although I’m neither a sociologist nor an anthropologist, I’ve come up with two theories.

My first theory is that each part of the pirate motif is a metaphor for the cold lives many of our residents left behind.

For instance, the peg leg is a symbol of the snow shovel that once burdened their mornings. The eye patch reminds them that they once dodged sharp icicles upon exiting buildings. The plank is an icy sidewalk of doom.

In this theory, our locals don’t really celebrate the pirate, but rejoice in their freedom from the pirate.

My second theory is that Punta Gorda residents really like boats. And if you insinuate there’ll be a chance to even look at a cool boat, they’ll show up.

Do You Have a Theory?

I hope you go to the Pirate Fest this weekend. While you’re there, take a moment to ponder your own theory. As you sit by the water cocktail in hand, enjoying the festivities with the rest of our tight-knit community, maybe you’ll come up with your own ideas on why our locals always seem to be celebrating.

If you come up with something, let us know on Facebook. We’d love to hear your thoughts.


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