An inside look at Tampa’s Rough Riders’ Gasparilla prep

We took a behind-the-scenes look at the nonprofit’s months-long prep for Tampa’s swashbuckling pirate invasion + parade.


The fleet of floats is parked outside the Riders’ Tampa headquarters.

Photo by TBAYtoday.

For Tampa’s adults, Gasparilla weekend is the biggest show of the year. At least that’s how it feel to Bob Moeller.

Moeller is the 45th president of the Rough Riders, a Tampa nonprofit that honors the legacy of Theodore Roosevelt and his Rough Riders (The late US President once called Port Tampa home). Their uniforms of khakis, dark blue button-downs (Florida is too hot for wool), and Stetson hats are truly synonymous with Gasparilla.

Founded in 1978, the organization has more than 550 members and is easily spotted in the Bayshore parade with its train and coal car and fleet of Teddy Roosevelt-emblazoned floats. This is Moeller’s 13th parade with the Riders, and this year he will ride at the top of the coal car (the president’s seat).


The bead sale begins.

Photo by TBAYtoday

Maintaining the floats is a year-round job, he says. The club has a float ops team dedicated to prepping floats for the 14-some parades the Riders travel to— from Fantasy Fest in Key West to both Gasparilla parades just down the street. The new crop learns the ropes in the five parades before Gaspy — like walking with the beads and wearing the uniform.

“If you just take somebody off the street and ask them to do that, they’ll be tripping down the street, hurt themselves and not have any idea what to do,” Moeller explains.

But Gasparilla is the biggest parade of the year. And the role — and schedule — of president is daunting, Moeller said.

Forty pallets of beads are ordered and organized for members and other clubs to shop. Cases of water are stocked on floats. DJs, Cuban sandwiches, and 20 kegs of Bud Light are scattered throughout the regiment’s vehicles.

We paid a visit to the club’s headquarters — the home base for Gasparilla prep — during the pre-parade bead sale Wednesday night. The warehouse was packed with members picking up new attire, boxes of beads (each member typically buys one), dropping off gear on the floats, and toasting to the weekend.

Now, all that’s left to do is wait. The float ops crew will show up at 7 a.m. Saturday to ensure the floats, jeeps, and trolley are loaded for the parade. The crew leaves for the parade staging area at 9 a.m.

Moeller is ready to take to his perch Saturday.

“Even if you’ve never been on top of there, the only way I can describe Gasparilla from being inside the ropes and not being a spectator is you’re a rockstar for a couple hours. You’ve got tens of thousands of people screaming at just you. You know everybody wants to see you. So it’s exciting, and I’m really looking forward to it.”

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