Legend has it that Jose Gasparillo née Gaspar, "the last of the buccaneers," plundered over 400 ships over the course of 40 years of tyranny on the high seas. In no region did he make more of an impression than the Gulf Coast of Florida.
His primary pirating grounds ranged from the northernmost point of western Florida all the way south to Cuba. Throughout his tenure, Gasparillo developed a reputation for fearlessness and ferociousness, frequently killing all the men aboard a ship. The infamous pirate was also, of course, quite the ladies man, and he routinely elected to either keep the women he encountered as his personal concubines or ransom them back to their wealthy family members. While they waited to be ransomed, the women were trapped on nearby Captiva Island, which some claim gave the island its name.
Fast forward to 1904 when Tampa officials adopted the pirate as the "patron rogue" of their annual celebration. Secret meetings were held in which 40 members of the first "Ye Mystic Krewe of Gasparilla" planned a surprise attack on the city during the main parade. Clad head-to-toe in pirate garb and riding horses, the first so-called "invasion" was such a wild success that the townsfolk demanded it become a permanent feature.
These days, revelers take to the streets of Tampa to witness boats, pirates, parades, merriment, and more during the Gasparilla Pirate Festival (or simply "Gasparilla" to locals), celebrating the world's yet-undiscovered treasure as well as the pirate's legacy of being a "hearty old swashbuckler with courtly manners and possibly – just possibly – prankful habits."
The modern incarnation of Ye Mystic Krewe numbers more than 700 of the city's most prominent leaders, who continue the traditional invasion by cutting through the harbor aboard the "pirate ship" Jose Gaspar (commissioned by the Krewe in 1954). After the invasion, a pirate parade streams through town, tossing beads and encouraging much grog-swilling. Without fail, the turnout for Gasparilla is massive, so come prepared. It's also advised that you wear your finest pirate garb.
Though the majority of Gasparilla is distinctly adult in nature, a parallel festival known as "Children's Gasparilla Extravaganza" is held the week prior for more family-oriented good times.