The Gasparilla Pirate Festival (late Jan./early Feb.) is actually two separate events. The original Gasparilla Pirate Fest is put on by Tampa ’s own Ye Mystic Krewe of Gasparilla, a New Orleans–style civic organization formed in 1904. Every year since then, with only 10 wartime exceptions, the Jose Gasparilla pirate ship sails into Tampa Bay  and the pirates “invade” the city, parade-style, tossing beads to increasingly inebriated partiers.
Live music happens throughout the day on enormous stages, there’s an amusement park-style midway with rides and games, and vendors are out in force. Note that the Mardi Gras similarities are intentional, and this is a decidedly bacchanalian event. It’s not adults-only, by any means, although beads are tossed according to a very similar, uh, “barter system” as in the French Quarter, and young kids could get a little overwhelmed by the crowds of red-nosed grown-ups.
If you fear the event may be too much for the little ones, the weekend before the Pirate Fest is the family-friendly Gasparilla Extravaganza, which features a children’s parade and fireworks and is alcohol-free, which means the tykes are a whole lot less likely to see Uncle Joe peeing in the street.
With the area’s phenomenal weather, it’s not surprising that outdoor festivals are a regular occurrence. Guavaween (Oct.) happens the last Saturday of October in Ybor City . The Halloween theme is localized with Latin American influences, and the affair is nearly as legendarily decadent as Gasparilla. The day begins with family-friendly activities like trick-or-treating and costume contests. From 4 p.m. on, live music, adult-oriented costume contests, and the legendary “Mama Guava Stumble Parade” draw some 80,000 people to the streets of Ybor.
Believe it or not, Tampa  does host a number of festivals and events that aren’t based around drunken revelry. The Tampa Bay Black Heritage Festival (Jan.) and the Cigar Heritage Festival (Nov.) celebrate different aspects of the area’s culture with plenty of good times but far less decadence than Guavaween or Gasparilla.
The Gasparilla Film Festival (late Feb./early Mar.) and the Tampa International Gay and Lesbian Film Festival (Oct.) focus on the cinematic arts, and the annual MacDill AirFest (Mar.) is one of the U.S. military’s largest air shows; the two-day event brings out thousands of people to watch the Thunderbirds and other flight crews perform various aerial acrobatics.