Gasparilla, one of the largest annual events in the Tampa Bay area, is celebrated every year in late January with a pirate ship and flotilla arriving in Hillsborough Bay, followed by a large parade, live music, and a festival. This year, the festivities will start with an optional brunch at 10 a.m. on Saturday, January 25 at the Tampa Convention Center (for tickets, visit gasparillapiratefest.com). The “invasion” of the city will begin at 11:30 a.m.
The Gasparilla celebrations were started in 1904 as a nod to the historic tale of Jose Gaspar, who robbed many ships off the coast of Spanish West Florida in the late 18th and early 19th centuries. As the story goes, Jose Gaspar and his pirates wanted to retire with all of their loot in 1821, but Gaspar insisted on seizing one more ship before ending his life on the seas. Unfortunately for Gaspar and his pirates, the ship they chose was an undercover United States Navy warship. They were defeated by the Navy after a bloody battle, and Gaspar was not allowed to escape with his life.
In the first decade of the 20th century, city officials and businessmen started what is now a 
Starting at 2 p.m. on Saturday is the Gasparilla Parade of the Pirates. Once the mayor hands the krewe the key to the city, the parade will begin. The parade route this year starts at the corner of Bay to Bay Boulevard and Bayshore Boulevard. People and floats will travel along Bayshore Boulevard up to Brorein Street, where they turn east. They then continue on to Ashley Drive, where the parade continues by turning north. The 3.8-mile long parade terminates right in downtown, at the corner of Cass Street and Ashley Drive; everyone in the parade should reach this point by 5:30 p.m. Over 130 distinct groups will be marching in the 2014 parade, including 90 floats, 50 Krewes and all of the pirates belonging to the Ye Mystic Krewe of Gasparilla!
Ashley Drive, from Kennedy Boulevard to Cass Street, will play host to the Gasparilla Pirate Festival all day, from 10 a.m. to 10 p.m. Parade attendees will be able to enjoy food and drink from numerous mobile units, and they’ll also be able to enjoy live music on stages set up throughout the stretch of the Drive. Ashley Drive promises to be the “beating heart” of this celebration, from the early morning, before any boats can be seen in the Bay to late night, when the victorious pirates have gone home (or perhaps to Ybor City for more celebration!).
The Gasparilla night parade, an Ybor City tradition, will be held two weeks later, on February 8. Even though the debauchery of the night parade is still a few weeks away, it doesn’t stop GaYBOR from starting the party the day of the day parade. Here’s a rundown of what’s going down and where:
* Bradley’s on 7th: Bradley’s Boys will be dancing on the bar, and the patio will be open all night. No cover. Gasparilla “Invasion of the Divas” shows start at 11:30 and 1:15 and will be hosted by Joey Brooks, with Robyn Demornay and special guest Susan Whitney.
* Liquid Tampa: A pirate’s sword-themed party called “Shipwrecked!” will start at 9 p.m., hosted by Conundrum. Music provided by DJ Greg Anderson. A special drag show will be performed by Bella Summers and Jade Embers.
* G. Bar: DJ Kidd Madonny is coming from Miami and will be putting on a show consisting of his special mix of music and lights. Local VJ Charles Machado will be playing in the Hook-Up Lounge. There will also be ten hot pirate dancers! Doors open at 9 p.m.
* The Honey Pot: Tease Saturdays gives the girls something to party about. Multi-platinum recording artist Che’Nelle will be performing live. Amy Demilo, Alisa Summers and cast will be entertaining the crowd with a pirate-themed show. Doors open at 9 p.m.
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