Freebooter 01

A Pirate’s Life

For those who did not grow up along the Gulf Coast – from New Orleans to Tampa – the concept of a krewe may be unfamiliar. The term originally referred to societies in New Orleans that organized the city’s Mardi Gras festivities. It is thought to have been coined by The Mistick* Krewe of Comus, the organization that hosted the first Mardi Gras parade with themed floats in 1857. Nearly 50 years later, the concept of a krewe made its way to Tampa when New Orleans-born engineer George Hardee suggested the city host a Mardi Gras-style event…but with pirates. He gathered 50 young men and formed Ye Mystic Krewe of Gasparilla, inspired by the legend of pirate Jose Gaspar. The first parade of pirates was on horseback, with the pirates “invading” the 1904 May Day parade.

Today there are roughly 130 krewes throughout Florida, including locally based Westchase Krewe of Freebooters. While pirates are traditionally known to pillage and plunder, these modern-day pirates thrive on equal parts philanthropy and fun.

The Krewe was founded in 2003 as the Hernando Freebooters based out of Weeki Wachee. Those origins gave rise to their distinct trademark: the six mermaids that ride on the bow of their parade float. Captain Dean Landsman was part of that original Krewe. “I had recently moved to Tampa when a colleague asked if I was interested in being a Pirate? I didn’t know I had a choice! Best decision ever!”

In 2017, the Krewe relocated and officially became the Westchase Krewe of Freebooters. In January of 2018, they unveiled their new parade float, a pirate ship aptly named “The Montague,” that comes complete with two bathrooms, a bar, multiple decks and tons of hooks to hold all of those beads.


The Freebooters’ mission is to “provide a social, leadership, and charitable platform for the benefit of the community that we call home.” You’ll find the Krewe at all the signature Westchase events, including the Santa Parade, Westchase Egg Hunt, Thanksgiving Food Drive and serving up post-race beers at the Great West Chase. “We try to do all the things that make Westchase unique,” said Chuck Hoppe.

They also donate their time to host charitable events like their annual golf tournament benefitting the Westchase Charitable Foundation and a Veteran’s Day BBQ benefitting Operation Helping Hand.

“I enjoy the comradery of the Krewe, as we have monthly socials, but I love that the focus is not so much the parades, but taking part in activities that help out our Westchase community,” said Nathalie Kobel.

The Krewe’s social aspect and philanthropy also appealed to Dyan and Jason Pithers, who joined the Krewe in 2017 as Founding Captain’s Club Members, a small group of people that paid five years of dues up front to help fund a new float when the Krewe moved to Westchase. The Pithers have an additional incentive to play part-time pirate: They want to help keep the history of Gasparilla alive in Tampa. “Gasparilla is the third largest parade in the nation,” Dyan said.  “I absolutely love seeing the faces of excited kids and adults as we participate in the Gasparilla parades and throw beads into the crowd. It brings so much happiness to the crowds and keeps this incredible tradition alive.”

Jay Edenfield admitted that the parades were what originally drew him to the krewe, but he has grown to truly appreciate the charitable work. “I still really enjoy the parades,” he said. “I like seeing the kids’ faces when you give them beads at the Children’s Parade or the adults at Gasparilla and the Night Parade.”

Parade season is a definite perk of being a pirate. The Freebooters take part in four parades a year: the Children’s Gasparilla Parade, the Gasparilla Day Parade, the St. Yago Knight Parade and the Rough Riders St. Patrick’s Parade. “I did the Gasparilla parade as a spectator only once and that was enough for me to decide that if I wanted to go to the parade, I should join the Krewe,” Kobel said.

Recruitment for the Freebooters opens in June. Capacity is limited, but Landsman noted there are typically a few spots open each year. He added that while most of their activities take place in the Westchase area, members can live anywhere. “There is an expectation of volunteering to help with the Krewe activities and to be involved in supporting our charitable and other efforts,” Landsman said. “Most important, you must be a ‘pirate’ at heart!”

The Krewe is also actively recruiting mermaids. “This volunteer role affords you the opportunity to participate in our activities at no cost and we include all the beads and even provide the mermaid tails,” Landsman said. “As this a coveted role, we simply ask that if you commit to a date that you follow through.”

To learn more about becoming a Freebooter or a mermaid, visit or email

Photography by Heather Bossowski

*Mistick is the original spelling from the Pequot term “missi-tuk,” describing a large river whose waters are driven into waves by tides or wind.

Scroll to Top