Florida Rambler’s 2018 Pirate Festival Calendar

Posted by Bob Rountree

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 myth.

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 5/14/2018

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

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, May 4-6..

Fort Lauderdale Rotary Club Pirate Festival, May 12, 2018. Downtown on Riverfront at Esplanade Park. 11AM to 7PM. FREE Admission. LIVE entertainment, Pirate Shows, RAFT and Paddleboard Races, Costume Contests, Pirate Encampments, Live Cannon Demonstrations, BEER Garden & Food Trucks, Arts & Crafts. Kids Promenade with 34′ Climb-aboard Pirate Ship,

June 2018

Billy Bowlegs Festival — Fort Walton Beach, June 1-2, 2018 — 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 — 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 — Cancelled for 2018.

July and August 2018

Florida’s pirates are sipping rum runners in A/C this summer.

September 2018

Sept. 19 is ‘Talk Like A Pirate Day’

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 Haunted 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 — Unknown if this event will return in 2018.

Pirate Weekend, Fernandina Beach, Unknown if event will return in 2018.

December 2018

Cedar Key Pirate Invasion, Nov. 30-Dec. 2, 2018. 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.

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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 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

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

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

Florida Rambler’s 2018 Pirate Festival Calendar