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Florida Pirate Festivals (& stories)

Florida pirate festivals are a natural.

The state’s coastal waters, natural harbors and islands have a colorful history of pirates, smugglers and other miscreants. Some of the stories are grounded in authentic Florida history, while others are imaginative yarns born of Florida tourism.

But one thing is for sure. Where there was treasure, there were pirates, and they swarmed the eastern seaboard and Florida Keys to disrupt the flow of gold and other treasures loaded aboard galleons sailing to Europe from Central America and the Caribbean Sea.

Florida Pirate Festivals Calendar

Florida pirate festivals The "Jose Gasparilla" pirate ship
The “Jose Gasparilla” pirate ship invades Tampa Bay.

January

Jan. 21, 2023. Children’s Gasparilla Extravaganza, An alcohol-free event for children and their parents, celebrating the return of Gasparilla Season to Tampa Bay. Events include a bicycle rodeo, pre-schoolers stroll and children’s parade along Bayshore Boulevard, parachute jumps and a Piratecnic finale at 7 p.m.

Jan. 28, 2023. Gasparilla Pirate FestColorful, fully-rigged pirate ship Jose Gasparilla appears at the south end of Hillsborough Bay, where the invading Ye Mystic Krewe of Gasparilla are met by a flotilla of pleasure craft intent on defending the city but succumbing to overwhelming pirate power in an epic battle. After the invasion,theGasparilla Parade of Pirates celebrates the capture of Tampa. Pirates toss trinkets to the conquered masses along Bayshore Boulevard, then into downtown Tampa. A spectacle with floats and marching bands.

February

Feb. 11-12, 2023. Treasure Coast Pirate Fest  Pirate-themed attractions, a living history pirate encampment, sword fighting, Blackbeard’s ship, a Little Buccaneer Kids Zone, Treasure Hunt, pirate weapon demonstrations and live music. Continuous entertainment throughout each day. Admission is free, although a $2 donation is encouraged.

March

Mar. 4, 2023. Gasparilla’s Outbound Voyage The merriment resumes as Ye Mystic Krewe of Gasparilla marks the conquest of Tampa once again with a festive celebration at Channelside that includes live music and spectacular bon voyage as Tampa’s favorite pirates make ready to sail back out to Tampa Bay.

March 4, 2023. Searle’s Sack of St. Augustine. Re-enactment of legendary pirate Robert Searle’s attack on St. Augustine. This deadly raid was led by Robert Searle in 1668 when he and his crew laid siege upon the city. Includes a historic encampment and an authentic battle.

March 25-26, 2023. Longwood Pirate Seafood Festival. Variety of food vendors, pirates and mermaids. Dress like a pirate, wear a mask! Due to social distancing standards, no kid zone or pirate ship this year. Admission is free. Free parking at Orlando Health South Seminole Hospital. Sat 10 am-6 pm, Sun 10 am-5 pm. Reiter Park, 311 W Warren Ave, Longwood.

Drake's Raid (Photo courtesy Visit St. Augustine)
Florida Pirate Festivals: Drake’s Raid (Photo courtesy Visit St. Augustine)

May

May 13, 2023. Drake’s Raid — St. Augustine. Annual re-enactment of Sir Francis Drake’s Raid on old San Agustin during the Anglo-Spanish War. The Spanish settlement of St. Augustine was captured in small fight and burned by an English expedition fleet led by Sir Francis Drake, a privateer commissioned by England’s Queen Elizabeth I.  Living history encampment on Friday is at the Fountain of Youth, 11 Magnolia Avenue, St. Augustine. The re-enactment on Saturday begins at the City Gate at the north end of St. George Street, and will proceed to the Plaza de la Constitution.

May 19-22, 2023. Billy Bowlegs Festival in Fort Walton Beach. It started out as a water skiing festival in 1953, and has turned into one of the nation’s longest-running and most popular pirate festivals. Highlights include Friday’s Skirmish with Billy Bowlegs at Fort Walton Beach Landing, Saturday’s Landing of Billy Bowlegs at Fort Walton Beach Landing and Sunday’s Torchlight Parade on Eglin Parkway from First Street to K-Mart. Throughout the festival, there will be continuous entertainment and children’s Pirate Play Zone.

September

September 19 is ‘Talk Like A Pirate Day’

October

Oct. 6-8, 2023. (Date not confirmed) Pirates of the High Seas Fest , Panama City Beach. Annual event celebrates the legacy of the pirates who once roamed the Gulf of Mexico and pillaged the Emerald Coast, telling the tale of Dominique Youx and his krewe of loyal buccaneers through staged pirate battles and storytelling. This event is held on Columbus Day Weekend at Pier Park and Grand Lagoon. In 2021, it is a blend of virtual and in-person events.

November

November 3-5, 2023. (Date not confirmed) Cedar Key Pirate Invasion, Battle on the Beach with historic weapon demonstrations and a pirate encampment.The festival wraps up each evening with a festival of music and dancing on Dock Street.


Florida pirate stories

Florida’s Atlantic Coast was strategically important for the protection of Spanish galleons that plied their way home with precious metals plundered from South America and the Caribbean.

Heavily-laden vessels called the plate fleets followed the Gulf Stream along the Florida coast, where pirates would prey on the fleets from hidden sanctuaries in the Keys and the aptly named Treasure Coast.

Hurricanes created additional hazards, sometimes wrecking the ships on reefs and shoals, where pirates would be waiting on our beaches to see what washed ashore.

Survivors of the wrecks were sold into slavery or ransomed, while others were tortured to force disclosure of where a ship sank.

Florida Pirate Festivals mclarty treasure museum Florida Pirate Festivals (& stories)
McLarty Treasure Museum.

In 1715, a Spanish treasure fleet of 12 galleons gathered in Havana and sailed for Spain, only to face a hurricane seven days later off the coast of what is now Vero Beach.

All but one of the ships was lost in the storm.

A thousand sailors perished while a small number survived on lifeboats. Many ships took part in the initial salvage when pirates, led by the English privateer Henry Jennings and others, staged raids on Spanish divers.

To this day, some artifacts and even coins still wash up on Florida beaches from time to time.

Florida Pirate Festivals: Gold coins at the St. Augustine Pirate Museum.
Gold coins at St. Augustine Pirate Museum. (Photo by Bonnie Gross)

Florida’s coastal sanctuaries offered refuge to bandits, incorrigible merchantmen, cutthroats and runaway slaves, creating a recruiting center for pirates and privateers in search of easy pickings from the Spanish fleets.

St. Augustine was established in 1565 to protect those fleets as they sailed up our coast toward home.

In 1586, St. Augustine was sacked and burned by the English privateer Sir Francis Drake, and in 1668, English pirates led by the corsair Robert Searles looted and burned St. Augustine

In 1683, a fleet of English privateers set out from the Bahamas to attack St. Augustine but, after losing ships in a storm, were captured by the vigilant Spanish when they landed north of the settlement to find supplies. And in 1686, French pirates led by Nicholas Grammont were repelled in their attack on the city.

When visiting St. Augustine, you can see rare artifacts and interactive exhibits at the St. Augustine Pirate and Treasure Museum, described here in a Florida Rambler article.


The Legend of Black Caesar

Black Caesar the pirate
Black Caesar

As the story goes, “Black Caesar” escaped a slave ship during a hurricane after befriending a white sailor. The pair escaped in a longboat loaded with ammunition and supplies.

Posing as shipwreck sailors, the pair hailed passing vessels for help. Once the ships came close enough, they pulled their guns and robbed their would-be rescuers.

This scheme went on for years, until the two men had a falling out over a woman that resulted in a duel. Black Caesar killed his longtime friend and over time took on more pirates and began attacking ships on the open sea.

Legend had it he amassed a fortune, which he stashed on Elliot Key, north of Key Largo, where he also assembled a harem of 100 women and a prison for men he hoped to ransom.

Pairing up with another infamous pirate, Blackbeard, Black Caesar was captured in 1718 off the coast of North Carolina as Blackbeard died at the hands of Lieutenant Robert Maynard.  Black Caesar was hanged for his crimes in Williamsburg, Va. Read more: Legend of Black Caesar Haunts the Florida Keys

The Legend of Gasparilla

The authentic pirate action played out along Florida’s Atlantic Coast, but that didn’t stop the tourism-hungry Gulf Coast from inventing it’s own.

In the early 1900s, the legend of Jose Gaspar was born in the marketing brochures of Gulf Coast hotels and railroads. Folklore has it that Gaspar, known as the fearsome Gasparilla, once served as a Spanish naval officer, only to break away and establish a base for a gang of thieves and swashbucklers near Boca Grande on the island that bears his name.

And — surprise! surprise! — rumor has it you may find buried treasure there!

Alas mateys, the legend loses luster with the discovery of “Gasparilla” on maps dating well before Gaspar (1756-1821).

Still, Florida loves its pirates, even one birthed in a jolly myth, and the Gasparilla Pirate Fest, held in Tampa every year since 1904, has grown to become the state’s grandest pirate festival of them all — held in late January every year in Tampa.

Meet a few famous Florida pirates

Anne Bonny — Though she never commanded a ship, Anne Bonny is remembered as one of few female pirates in history.

Blackbeard display at St. Augustine Pirate Museum
Florida Pirate Festivals: Blackbeard

Blackbeard (Edward Teach) — Blackbeard was known for his fearsome appearance. His life was romanticized after his death and became inspiration for a many pirate-themed works of fiction.

Calico Jack (John Rackham) — “Calico Jack” was a pirate of the Caribbean and Florida, noteworthy for his design of the famous “Jolly Roger” pirate flag and his two female crew members, Mary Read and Anne Bonny.

Mary Read — Born in England to the widow of a sea captain.  After her husband died, she dressed as a man, was captured by pirates, and became a pirate herself.

Sir Francis Drake — Possibly the most renowned seaman during the reign of England’s Queen Elizabeth I, Drake sacked the Spanish fleets in Florida many times as a privateer under order of queen herself, eventually crushing the Spanish Armada.

Captain William Kidd — Rumors of his buried treasures created a legend around this notorious pirate, awakening the imagination of the world when Robert Louis Stevenson wrote Treasure Island in 1883.

Stede Bonnet — Known as “The Gentleman Pirate,” Bonnet was well-educated and respected by those who knew him. Bonnet was a retired major in the King’s Guards who lived with his wife on a large estate in Barbados, turning to piracy in the early 18th Century.

Black Caesar — A captured slave turned into a pirate who was active off the Florida Keys for a decade, he would later serve as a lieutenant under Blackbeard.

John LaFitte — A French-American pirate and privateer in the Gulf of Mexico during the early 19th century, a persistent rumor has always been that Lafitte rescued Napoleon from exile so both ended their days in Louisiana.


Florida’s pirates missed this treasure

On September 10, 1622, a twenty-eight ship convoy left Havana headed for Spain, loaded to the gunwales with treasure from South and Central America.

A two-day hurricane ended the voyage for eight of the ships. Among these were the Santa Margarita and the Nuesta Senora de Atocha, destined to become among the most famous and richest shipwrecks in history.

As with most shipwrecks, Spain attempted to salvage what it could, and pirates would attack and seize the recovered treasures.

In 1969, treasure hunter Mel Fisher began a relentless 16-year quest for the Atocha, first uncovering gold bars in 1973, and by 1985, his team had salvaged a fortune in gold, silver, coins, artifacts and emeralds from the wrecks of both the Atocha and the Santa Margarita. Some of the treasure can be viewed at Fisher’s nonprofit Maritime Heritage Museum in Key West.

Pirate Clubs

More Pirate Links

2023 Florida Seafood Festivals Calendar

Read these books!

Links below go to Amazon. We may receive a modest commission if a purchase is made.

Treasure Island by Robert Louis Stevenson

Pirates of the Florida Coast: Truths, Legends, and Myths by Robert Jacob

Florida Pirates: From the Southern Gulf Coast to the Keys and Beyond  by James Kaserman and Sarah Kaserman

Pirates and Buried Treasures of Florida by Jack Beater

Notes from the editor:

The information in this article was accurate when published but may change without notice. Confirm details when planning visits.

This page may include affiliate links from which we earn modest commissions if a purchase is made. 

This article is property of FloridaRambler.com, protected by U.S. Copyright Law. Re-publication without written permission is against the law.


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Bonnie Gross

Monday 8th of May 2017

Thank you! We have updated our story.

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