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Many say the legend is apocryphal, others swear it’s true, but supposedly a pirate named Jose Gaspar—who called himself “Gasparilla”—terrorized the coastal Gulf waters of Florida during the late 18th and early 19th centuries.

Now here’s where it gets iffy, because some believe that Gaspar returns to Tampa every year during the annual Gasparilla Pirate Festival, which features an “invasion” of buccaneers aboard a 165-foot pirate ship named, of course, the Jose Gasparilla. Leading a fleet of other boats, the ship cruises up Tampa Bay and lands in downtown Tampa; from there, a street parade takes over, attended on average by over 400,000 people.

As you might guess, pirates are big in this part of Florida, whether you’re talking about the favored home team, the NFL Tampa Bay Buccaneers, or the many pirate-themed parties and events planned and executed by Tampa-based BayArea Destination Management Company. In fact, a great number of the firm’s events are held at the Bucs’ Raymond James Stadium, home to a replica pirate ship whose cannons are fired every time the team scores.

“It’s at a great location within the stadium where we can actually do functions, and we bring in our pirates and attendees dress up as pirates,” reports Karn Clark, co-owner of BayArea Destination Management.

In addition to the stadium ship, Karn also brings smaller replica ships to host themed events on-site at the Tampa Convention Center and area hotels, while yet another pirate ship is available for dinner cruises on Tampa Bay, the Gulf of Mexico and the Intracoastal Waterway.

Other programs requested by meeting planners include jaunts to Tampa’s historic Ybor City, a former cigar capital which today is a colorful entertainment center of shopping, dining and live music but still home to those who practice the art of cigar rolling, and don’t mind an audience when they do.

“People love to see cigars being hand-rolled because it is indeed an art,” Clark says. “Whether they smoke them or not, they appreciate the talent it takes to make them so they hold together when you light them.”

Clark also gets requests for Busch Gardens programs, including upscale dinners and scavenger hunts with team-building components. It’s the smaller groups, though, that truly get to go behind the scenes by hitching a ride on feed trucks to watch the animals get fed.

“They’re right there, face-to-face with the animals, and they have a great time,” Clark says. “That could be followed by cocktails and dinner.”

Cocktails, dinners, beach barbecues, build-your-own-boat... the list of group activities in Tampa Bay goes on and on.

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About the author
Lisa Simundson