Festivals / Florida Roundups

Florida Rambler’s 2018 Pirate Festival Calendar

Florida’s coastal waters, natural harbors and islands have a colorful history of pirates, smugglers and other miscreants.

Some of the stories are real with firm roots in authentic Florida history, while others are simply yarns born of Florida tourism myths.

The legend of pirate Black Caesar still haunts the Florida Keys

2018 Pirate Festival Calendar

Warning: Some links automatically launch unexpected pirate music that may not be suitable for the workplace.

Updated 1/3/2018

January 2018

Children’s Gasparilla Extravaganza, Tampa, January 20. 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.

The "Jose Gasparilla" pirate ship

The “Jose Gasparilla” pirate ship

Gasparilla Pirate Fest, Tampa, January 27, 2018. Colorful, 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, Gasparilla 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 2018

Treasure Coast Pirate Fest Fort Pierce, Feb. 2-4, 2018. 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 2018

Gasparilla’s Outbound Voyage —Tampa, March 3, 2018 — 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.

Searle’s Sack of St. Augustine. — St. Augustine, March 2-3, 2018. 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.

April/May 2018

Fernandina Beach Pirate Parade, May 3, 2018. Parade kicks off the Isles of Eight Flags Shrimp Festival.

Flagler Beach Pirate Invasion, 2018 Dates TBA, Flagler Beach. The invasion occurs at 11 a.m. Saturday with music, vendors, a parade and a pirate’s ball Friday night, Veterans Park, 105 S 2nd St, Flagler Beach. (Unknown if the event will return for a second year.)

June 2018

Billy Bowlegs Festival — Fort Walton Beach, 2018 dates TBA  — 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. The Billy Bowlegs Pirate Festival always takes place on the first full weekend in June. Returning this year is Saturday’s Billy Bowlegs Beer Tour from 12 noon until 4 p.m., when you can sample craft beers from local brewers. Throughout the festival, there will be continuous entertainment and children’s Pirate Play Zone.

Drake's Raid (Photo courtesy Visit St. Augustine)

Drake’s Raid (Photo courtesy Visit St. Augustine)

Drake’s Raid — St. Augustine, June 2, 2018  –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 Constitucion.

Cocoa Beach Pirate Fest — Cocoa Beach, 2018 dates TBA — Featuring a live history pirate encampment, musical entertainment featuring sea shanties, pirate songs, traditional Irish tunes and tavern songs. Event has moved to the Radisson Resort at the Port, 8701 Astronaut Boulevard, Cape Canaveral.

July 2018

Vero Beach Pirate Fest — Vero Beach, 2018 dates TBA. Held under the canopy of 300-year-old oak trees that stood on this site when pirates converged here to loot the 1715 shipwrecks; event features reenactments, authentic weapons, artifacts, treasure exhibits, themed vendors, treasure hunts, mermaids and entertainment.

August 2018

Florida’s pirates don’t do anything in August except drink rum runners in air-conditioning. 🙂

September 2018 

Sept. 19 is ‘Talk Like A Pirate Day’

Fisherman’s Village Pirate Festival, Punta Gorda, 2018 Dates TBA. Last year’s event was cancelled, and it’s unknown if the festival will return in 2018. Pirate battles, Blackbeard’s pirate ship, hear cannons thunder, visit a pirate encampment, grab a cold beer and meet a live mermaid.

October 2018 

Pirates of the High Seas Fest — Panama City Beach, 2018 dates TBA, but the event is normally held on Columbus Day Weekend at Pier Park and Grand Lagoon.

Fort Myers Beach Pirate Festival — Fort Myers Beach, 2018 dates TBA. (Columbus Day Weekend)

Boynton Beach Pirate Fest and Mermaid Splash — Boynton Beach, 2018 dates TBA. East Ocean Avenue is transformed into Hobb’s Cove, a bustling old world port brimming with pirate superstitions and pirate ghosts. Brave souls will find seven stages with continuous live entertainment. Enjoy a costume contest, parade and mermaid pageant.

November 2018

Saint Arrrgustine Pirate Gathering — St. John’s Marketplace, St. Augustine, 2018 Dates TBA. Pirate encampment and festival, demonstrations, entertainment stages and late-night revelry. Unknown if this event will return in 2018.

Pirate Weekend, Fernandina Beach, 2018 Dates TBA. Unknown if event will return in 2018. Sponsored by the Fernandina Beach Pirates Club.

December 2018

Cedar Key Pirate Invasion, 2018 dates TBA. 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.


The authentic pirates of the Atlantic Coast

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 through the Florida Straits 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.

The Treasure Coast

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.

St. Augustine

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.

The Florida Keys

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.

The Legend of Gasparilla 

The "Jose Gasparilla" pirate ship

The “Jose Gasparilla” pirate ship

Authentic pirate action played out along Florida’s Atlantic Coast, but that didn’t stop 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.

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


    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.

Pirate Clubs

Pirates of the Treasure Coast

Ye Mystic Krewe of Gasparilla

St. Augustine Swashbucklers

Fernandina Beach Pirate’s Club

St. Mary’s (Georgia) Pirate Club

More Pirate Links!

St. Augustine Pirate and Treasure Museum

Mel Fisher Maritime Museum, Key West

Mel Fisher’s Treasure Museum, Sebastian

Pirates Dinner Adventure: Save Over 40% on Dinner Tickets! (Sponsor)

Treasure Tavern: Dinner Show – Special Offer Save Over 40%! (Sponsor)

Check out Florida Rambler’s popular Seafood Festival Calendar

Event organizers: If you have additional detail to add for your event, feel free to leave comments.


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  1. Bonnie Gross says:

    Thank you! We have updated our story.

  2. Your dates are incorrect for the Cocoa Beach Pirate Festival. It is June 16-18, not 9-11.

  3. durandconnie says:

    My friend and I sure miss the FL Keys not having a festival and ball!

  4. Hi Jessica,

    Thank you for bringing this pirate event to our attention. We have added it to our pirate festival guide!

  5. January 21, 2017 is our upcoming annual Pirate Day on Marco Island at the Marco Island Historical Museum from 11-2. A fun and family friendly event! For more details visit http://www.colliermuseums.com

  6. Many thanks for bringing this festival to my attention. I have updated the article and will add more as I find out more about it. 🙂

  7. Tim Cook says:

    *family friendly

  8. Tim Cook says:

    Boynton Beach Haunted Pirate Fest and Mermaid Splash – 10/21-10/23. This is a great day friendly event that should be added to this list!

  9. debbie becker says:

    Your information on upcoming event will assist us greatly in additional participation. We were at Vero Beach Pirate Festival with our USS Essex. Check us out on Facebook:
    Custom Radio Controlled Boats. 14ft Tugboat; 18ft USS Essex, {USWarship captured by Mediterranian Pirates} and 16.5ft Shrimp Trawler. Thank you.

  10. This is a GREAT website! We attend many more FL events because if it. Thank you!!

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