Find Pirate Festivals & Events in Florida

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Black Caesar Pirates Festival, Key Largo (October). Rum-tasting, pirate parades, costume contests and a thieves market set the mood for this swashbuckling event. keylargopiratesfest.com

Fort Myers Beach Pirate Festival, Fort Myers Beach (October). This fest features a “pirate invasion” and a ship-to-shore battle with real black powder cannons. There are two stages with live entertainment, pirate reenactors, storytellers and other family entertainment. beachpiratefestival.com

St. Arrrgustine Pirate Gathering, St. Augustine (November). The Crews of the Black Heart, Ancient City Privateers and Brothers of the Coasts lead this celebration of the Golden Age of Piracy in the nation’s oldest city. There’s a pirate mutiny, weapons demonstrations, sailors encampment and thieves market, among other diversions. pirategathering.com

Florida Pirate Festival, St. Petersburg (November). Vinoy Park in St, Petersburg is the home for this pirate-themed celebration, based on an 18th Century tale of pirates battling against forces of law and order. piratefair.compirates-word2

Pirates in Paradise Festival, Key West (late November/December) Re-enactors and stunt men from around the country invade the island for a host of escapades. Visitors are likely to encounter the likes of Anne Bonny, Bawdy Be, Braze, Cascabel, Sir Henry Morgan, The Pyrates of the Coast, the Bone Island Buccaneers (Key West’s own pirate crewe) and other nefarious Brethren of the Coast. piratesinparadise.com

Gasparilla Pirate Fest, Tampa (January). Legendary pirate Jose Gaspar is the namesake of this rowdy celebration, an annual tradition in Tampa since 1904. In addition to the festive mock invasion, Gasparilla celebration includes a week’s worth of activitiesgasparillapiratefest.com

The Pillage at the Village at the Florida Renaissance Festival, Deerfield Beach (February). The Pillage at the Village is a featured attraction of the annual “pirate’s weekend,” part of the extended run of Renaissance Fest events that take visitors back in a time capsule. ren-fest.comdownload (1)

Pirates Sack St. Augustine, Searle’s Raid, (March). This reenatment commemorates the 17th Century Raid by Captain Robert Searle. It start at St. Augustine’s Downtown Plaza and heads north. staugustineinfo.com

Isle of Eight Flags Shrimp Festival, Fernandina Beach (May). A pirate parade, featuring members of the Fernandina Beach Pirates Club, kicks off the Isle of Eight Flags Shrimp Festival Shrimp, a tradition for more than 45 years. There’s also arts and crafts, fine arts, live music and, of course, shrimp. shrimpfestival.com

John Levique Pirate Days, Madeira Beach. (June). This fest celebrates the discovery of John’s Pass by turtle farmer John Levique after the hurricane of September 1848. Activities include a Pirates Ball, children’s and adult’s costume contests, a village-wide treasure hunt, pirate invasion followed by a parade and “pillaging” of the village. johnspassfestivals.compirate-treasure

Billy Bowlegs Festival, Boynton Beach (June). Local and regional bands, food, arts and crafts, pirates, a torchlight parade, children’s activities and fireworks are part of this annual pirate-themed event. fwbchamber.org

Drake’s Raid, St. Augustine (June). Re-enactment action is based at a 16th century encampment at the Fountain of Youth. Military drills and other period demonstrations lead to a battle with swords and black powder muskets in the historic Plaza de la Constitucion in downtown St. Augustine. staugustineinfo.com

Treasure Coast Pirate Fest, Stuart (September). A family treasure hunt, adult and children’s costume contests, pirate-themed merchandise, food and three stages of live entertainment and pirates are highlights of this free festival. treasurecoastpiratefest.com

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