Gasparilla: Was the Legendary Spanish Pirate Jose Gaspar Real? - Historic Mysteries (2023)

In the late 18th and early 19th centuries, no pirate was more feared in the southern United States than Jose Gaspar. With his crew of cut-throat mercenaries, the “last of the buccaneers” terrorized shipping in the Gulf of Mexico for years, striking from his secret Florida base.

Florida at this time was in its “Second Spanish Period” which runs from 1783 to 1821. In this time Spain controlled a huge swathe of the Americas and Gaspar grew rich. Legends tell how he amassed a huge fortune, and hid an enormous treasure before dying a hero facing the might of the US Navy.

Or at least that’s what Florida folklore would have you believe. However there are several problems with the story which have led many to question whether “Gasparilla” as he was known was a real historical figure.

So, a real figure or a tall tale told by Floridians? Who was this figure, and what was he supposed to have done?

The Story of Jose Gaspar

José Gaspar allegedly lived between 1756 and 1821 and was based on southwest Florida, on the edge of the Gulf of Mexico. He was said to have been extremely active for many years, attacking merchant ships and evading justice, and in this time he won himself a huge fortune.

However, even from the first we run into different versions of the story. In different accounts, details of his early life, motivations, and activities varied.

According to some versions of the story, Gaspar started as a troubled adolescent who kidnapped a little girl for ransom. When he was captured and offered the option of going to prison or joining the navy, he chose the latter, serving with distinction for several years before organizing a mutiny against a dictatorial captain and fleeing to Florida with a stolen ship.

(Video) The history and legacy of Jose Gaspar

According to other versions of the narrative, Gaspar was a nobleman who rose through the ranks of the Spanish Royal Navy and became a councilor to King Charles III of Spain. He was well-liked in court, but when he abandoned one lover for another, his spurned lover falsely accused him of stealing the crown jewels. When he was wrongfully arrested, he hijacked a ship and fled, promising to seek revenge on his homeland.

Canny readers will already recognize a certain romantic streak in these stories. Gaspar is presented as dignified, noble in heart and rich and titled in some versions. His piratical career always starts with an injustice and he is seen as a lovable rogue rather than a murderous monster.

No Ordinary Pirate

This characterization continues through the stories of Gasparilla as a pirate. When a ship was taken, the people aboard were not immediately murdered but instead offered the option of dying or joining Gasparilla’s crew. Many took the deal.

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Captured ladies were not raped and murdered, but instead had the option of marrying one of his crew members or being transferred to Captiva Island in Florida. If marriage was selected, there would be a ceremony, and the marriage promise would be strictly enforced.

Although Gasparilla was a well-educated, well-dressed pirate and ladies’ man, things did not always go as planned. One such account concerns Maria Louise, a lovely Spanish princess, who was returning to Spain after a journey to Mexico with 11 Mexican princesses who were to be educated and married in Spain.

Gasparilla seized their ship, as well as their 11 dowries, but fell madly in love with the Spanish princess. However there is a salacious twist to this tale, in that when this lovely young girl declined his romantic proposition, he had her executed.

Despite his brutal reputation, Gasparilla was supposed to have a soft side as well. On one occasion, his right-hand man Lopez had become tired of the pirate life and desired to return to Spain to see his love, Sanibel, after 13 long years. Gasparilla not only granted Lopez permission but also bestowed his blessing on his long-time friend, providing a ship and several men to accompany him back to Spain.

Another instance of his softer side can be found in the account of Ann Jeffries, an English girl traveling from New Orleans to Liverpool. Gasparilla seized her ship, and the hostages were brought to his hideout on Gasparilla Island.

(Video) Episode 0003: Unmasking the Legend: The Real Story of Jose Gaspar - Pirate or Myth?

Gasparilla fell in love with Jeffries while on land, but she informed him that she had fallen in love with one of his crew, Batista Fuentes, a handsome and well-educated man from a famous family. When Gasparilla requested that they accompany him and his crew on a raid, the two young lovers assumed they would be slaughtered.

Instead, he pursued a merchant ship and insisted that it convey Batista and Ann Jeffries to England and that its captain marry them on board after they were out of sight of his ship, the Jose Gasparilla II.

However, perhaps the most famous story of Gaspar concerns his death. Gasparilla had decided to retire following the sale of Florida to the United States, and was dividing his treasure (valued at six times the purchase price of the entire state of Florida) between his crew.

However, he spotted a British merchant ship and could not resist one final prize. This was to prove his doom as the ship he had targeted was no harmless cargo ship but in fact the USS Enterprise, a heavily armed and very dangerous pirate hunter.

During the final combat, the majority of Gasparilla’s crew was killed, but there were 12 survivors – 11 men and a cabin boy called Juan Gomez. The men were executed but Gomez was to be the final survivor of this piratical outfit.

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He was sentenced to prison and eventually released. Many of the stories about Gasparilla were attributed to Juan Gomez. He enjoyed telling stories about his adventures on the high seas and a large amount of Gasparilla’s treasure that was never discovered.

But Gasparilla himself did not survive the final battle. Rather than be captured by the United States Navy, he wrapped an anchor chain around his leg and jumped overboard, the heavy metal dragging him out of sight into the deep blue waters.

(Video) The legend of Jose Gaspar and the history of Gasparilla

Was he a Real Person?

Tales of love and marriage, an aristocratic captain with nobility in his crew, a handsome and debonair adventurer: all these stories seem too good to be true. And indeed there are serious problems with the stories of Gasparilla.

For one, there is no evidence of his pirate empire. No contemporaneous mention of his existence or achievements has ever been found in Spanish or American ship logs, court documents, newspapers, or other archives, and no tangible items associated with Gaspar have been unearthed in the area where he is said to have operated.

The first recorded reference of José Gaspar was in fact over 100 years after his supposed career, in a short biography included in an early 1900s promotional brochure for the Gasparilla Inn on Gasparilla Island in Charlotte Harbor.

The author of the pamphlet readily stated that the spectacular tale was a work of fiction with no genuine facts in it. Subsequent retellings of the Gaspar tale are based on this imaginative account, including the unintentional inclusion of José Gaspar in a 1923 book on genuine pirates, which has created ongoing debate regarding his historical veracity.

The Gasparilla Inn was a hotel on the island. According to archives, the island community was created by Albert W. Gilchrist, Florida’s 20th governor. In 1897, he purchased land at Boca Grande, an island outpost. Gilchrist intended to turn the area into a community.

The legend of Gaspar was first recorded in promotional materials for this Boca Grande Hotel. Charlotte Harbor and Northern Railroad Company are said to have distributed the brochures. The leaflet establishes Gaspar’s legend, claiming that he chose Gasparilla Island as the best of the islands in Charlotte Harbor to establish his base.

So it would seem that Gasparilla is a fiction, no more real a figure than Mickey Mouse. However his name and supposed deeds are still celebrated to this day, not least with the annual Gasparilla Pirate Festival, which began in 1904 in Tampa, Florida, which honors his tale.

(Video) Museum at Home: The History of Gasparilla

Top Image: Real pirate or later fiction? Source: Theartofphoto / Adobe Stock.

By Bipin Dimri


Gasparilla: Was the Legendary Spanish Pirate Jose Gaspar Real? - Historic Mysteries (4)

Bipin Dimri

Bipin Dimri is a writer from India with an educational background in Management Studies. He has written for 8 years in a variety of fields including history, health and politics. Read More

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(Video) The History of Gasparilla


Gasparilla: Was the Legendary Spanish Pirate Jose Gaspar Real? - Historic Mysteries? ›

Upon closer investigation, historians have found no evidence that the pirate José Gaspar ever actually existed. According to Spanish archives, American ship logs, court documents and newspapers, there is no mention of the names "Gaspar" or "Gasparilla" in record.

Is Gasparilla based on a true story? ›

José Gaspar, also known by his nickname Gasparilla (supposedly lived c. 1756 – 1821), is an apocryphal Spanish pirate who terrorized the Gulf of Mexico from his base in southwest Florida during Florida's second Spanish period (1783 to 1821).

What is the story behind Gasparilla? ›

Gasparilla began as a surprise "pirate invasion" on horseback during the city's May Day festival in 1904. Over the next decade, the pirate parade was staged as an occasional add-on to other community events, with the highlight of the early period being the first seaborne invasion in 1911.

What are some fun facts about Gasparilla? ›

Since the first invasion in 1904, there have only been 11 years when Gasparilla was not celebrated, including in 2021 because of COVID fears. The Jose Gasparilla pirate ship was commissioned in 1954. According to the Gasparilla Pirate Fest website, it is the only fully-rigged pirate ship to be built in modern times.

Who invented Gasparilla? ›

Gasparilla began in 1904 when Miss Louise Francis Dodge, society editor of the Tampa Tribune, and George W. Hardee, then with the federal government in Tampa, conspired to promote the City of Tampa and its May Day celebration.

Did real pirates invade Tampa? ›

More than 750 swashbucklers invaded Tampa Bay aboard “Jose Gasparilla,” the only fully-rigger pirate ship in the world. After the ship docked at the Tampa Convention Center, Mayor Jane Castor surrendered the Key to the City to the Captain of Ye Mystic Krewe of Gasparilla. See photos of the invasion below.

Was Tampa Bay a pirate town? ›

Since 1905, pirates have invaded Tampa Bay. Every year, the unruly plunderers take over the city in honor of the mythical legendary pirate Jose Gaspar,” according to event history published by the City of Tampa.

What does Gasparilla mean in Spanish? ›

Rumor has it that when Gaspar died, he left an untold fortune in buried treasure somewhere along Florida's coast. To this day, it has yet to be found. "Gasparilla" literally means "little Gaspar" in Spanish.

Why do they throw beads at Gasparilla? ›

Why do they throw beads and coins from the parade floats? The idea of this is that the pirates are celebrating their capture of the city and parading in the streets. They have stolen so much treasure that they are now sharing it with everyone in the city.

What does Gasparilla mean in english? ›

Gasparilla may refer to: Gasparilla Pirate Festival, a large parade and related events held annually in Tampa, Florida. José Gaspar, also known as Gasparilla, a Spanish pirate from Florida folklore for whom the festival is named.

Can you swim in Gasparilla Island? ›

The pristine beaches at Gasparilla Island State Park offer something for every beachgoer. The 1-mile stretch of beach can be accessed from any of the five parking areas along the gulf and the Boca Grande Pass. Search for new shells, sunbathe, go swimming or walk along the beach.

Who owns Gasparilla? ›

The Inn is presently owned by the William Farish family. William Farish is a former United States Ambassador to The Court of St. James, and his wife, Sarah, is the only daughter of the late Bayard Sharp.

Can you drink at Gasparilla? ›

Consuming alcohol on public property outside these wet zones is prohibited. There is Zero Tolerance for underage alcohol consumption and disruptive behavior. Please drink responsibly.

How many people went to Gasparilla? ›

An estimated 300,000 revelers lined the streets of downtown Tampa on Saturday for the 2023 Gasparilla Invasion and Parade of Pirates, the third-largest parade in the country.

What do you wear to Gasparilla? ›

A jacket or tie is not required. Ladies' apparel should be comparable to the gentlemen, such as blouses, skirts, dresses, and dress slacks. Jeans, shorts or tank tops are not permitted. December 20, 2022 to April 30, 2023 gentlemen wear dress slacks, collared shirts and jackets for dinner.

Does Gasparilla cost money? ›

This event is free to the public. Reserved bleacher seating is available for the Seminole Hard Rock Gasparilla Pirate Fest .

What city had the most pirates? ›

1. Port Royal. During the “Golden Age of Piracy” in the late 17th and early 18th centuries, Port Royal, Jamaica stood as one of the most popular ports of call for thieves, prostitutes and pirates of every stripe.

Where did pirates sleep on land? ›

Sleeping Quarters

Some of them slept on hammocks. Others slept on the floor. It was easier for them to sleep on hammocks because they swayed and rocked with the ship's movements. They also didn't have to worry about falling off beds during storms or high tides.

Where did pirates stay in Florida? ›

The state is steeped in buccaneer history that stretches from Key West to Tampa Bay, St. Augustine to Fernandina Beach on Amelia Island, almost at the Georgia line. In the 17th and 18th centuries, Fernandina Beach was a safe harbor for pirates.

Why is Tampa called Tampa? ›

The origin of the city's name is uncertain; it may be derived from a Creek word for “near it” or “a nearby place,” for its proximity to the bay, or it may mean “split wood for quick fire,” in reference to driftwood on the shore used for firewood. The Port of Tampa is the state's largest deepwater port.

Do the Buccaneers still have the pirate ship? ›

Located beyond the north endzone at Raymond James Stadium, Buccaneer Cove, is modeled after a 19th century Pirate village. Costing $3 million, Buccaneer Cove's main attraction is a 103 foot long replica Pirate ship.

What island is named after a pirate in Florida? ›

Gasparilla Island is essential for enclosing the estuary that includes Pine Island Sound. The name “Friar Gaspar” appears on ancient maps drawn long before the mythical pirate was supposed to have lived. The pirate theme first appeared on a railroad brochure in 1904.

What is Florida called in Spanish? ›

Ponce de Leon claimed the land for Spain, calling it La Florida, the Spanish name for flowery, covered with flowers, or abounding in flowers. Something to do with flowers anyway.

What is the word Florida in Spanish? ›

From Spanish florida (“flowery”), often referring to a place's abundance of flowers. The state's name specifically is a shortening of la Florida (“the flowery one”) or Pascua Florida (“flowery Easter”).

What is Boca in Spanish slang? ›

This week's Spanish word of the week is boca. Boca is a noun that means mouth and you can find how to pronounce it here: You'll probably already know the basic meaning of boca, which is a person's or animal's mouth.

Why not pick up beads in New Orleans? ›

Picking up beads from the floor is considered bad luck in New Orleans. The streets also get rather unsanitary during Carnival season. So, practise your reflexes by catching the beads while they're still in the air.

What are some things you would see if you visited Tampa's Gasparilla Pirate Festival? ›

Hawkers sell pirate hats, plastic horns, and other trinkets while food trucks line the streets closest to the parade to sell their food and drink to parade goers.

How many floats are in Gasparilla? ›

More than 103 elaborate floats, five marching bands and over 50 distinct Krewes are making their way through downtown Tampa. The parade begins at Bay to Bay and Bayshore Boulevard.

Where exactly is Gasparilla? ›

Gasparilla Island is a barrier island in southwest Florida, United States, straddling the border of Charlotte and Lee counties. Its largest town is Boca Grande, and it is the location of the Gasparilla Island State Park.

Is Gasparilla only one day? ›

When is Gasparilla? Gasparilla Pirate Fest is on January 28, 2023 with the Parade of Pirates stepping off at 1pm. This is an all-day event though and so much more than a parade.

Is Gasparilla Island private? ›

Little Gasparilla Island is a private, bridge-less barrier island accessible “only” by boat. Take a 15 minute Water Taxi (runs 365 days a year) or bring your own boat (up to 26′) to our deep water dock that is shared with several other properties.

Are there alligators on Gasparilla Island? ›

As a matter of fact, Gasparilla Island features a large, wildlife friendly state park. Raccoons, opossums, bats, rats, mice, squirrels, snakes, osprey, skunks, iguanas, alligators, armadillos, and even feral hogs are all found on the island.

Do people live on Gasparilla Island? ›

The island is only accessible by private boat or water taxi and is predominantly single family homes, around 350, which are mostly part-time residents.

How deep is gasparilla pass? ›

The Boca Grande Pass, just off the southern tip of Gasparilla Island State Park, is world-famous for sportfishing, particularly tarpon. The pass connects the Charlotte Harbor to the Gulf of Mexico and is one of the deepest natural passes in Florida, reaching depths of 80 feet.

Did the Gasparilla Inn survive Ian? ›

Historic buildings such as the Port Boca Grande Lighthouse built in 1890 and the Gasparilla Inn & Club – which was built in 1911 and has hosted President George H.W. Bush, President George W. Bush, Henry Ford, Thomas Edison, Katharine Hepburn and many other famous people – survived Hurricane Ian, according to Cooper.

Can you bring your own alcohol to Gasparilla? ›

There will be eight vendors selling alcohol along the way. The city of Tampa is reminding Gasparilla participants of the following policies: No underage alcohol consumption. No open alcohol containers or consumption outside of designated wet zones.

Is Gasparilla alcohol free? ›

However, there no are alcoholic beverage vendors in this zone. Although it is not a wet zone, people are allowed to drink anywhere on Bayshore Boulevard from Gandy Boulevard to West Cleveland Street to get good views of the parade. There are also five other alcoholic beverage vendors on Bayshore Boulevard.

Can you drive a car on Gasparilla Island? ›

All access is either by private boat or water taxi. There are no roads, and therefore no cars, on the island, only a sandy cart path which allows you to traverse and explore the island by golf cart. The absence of street lights enhances the starry night sky which shines bright over LGI.

Are dogs allowed on Gasparilla Island? ›

Are dogs allowed on a leash - Gasparilla Island State Park. Dogs are allowed in the park if they are on a leash. They are not allowed on the actual beach. This is pretty typical of Florida beaches everywhere - however, there are some "dog beaches" throughout the state.

Can you walk around with a beer in Tampa? ›

– Consumption and possession of open containers on streets, sidewalks, alleys and other public property. (a) It is unlawful for any person to consume, assist or aid another to consume any alcoholic beverage upon any street, sidewalk, alley or other public property within the city.

Is Gasparilla big? ›

After all, the Gasparilla Parade of Pirates is known as the third-largest parade in the nation.

How many beads are thrown at Gasparilla? ›

An estimated 5.4 million individual strands of beads will change hands at Gasparilla or about 225,000 pounds of plastic. That's heavier than a space shuttle.

Can you bring kids to Gasparilla? ›

The Preschoolers' Stroll allows children ages 5 and under to strut their stuff along Bayshore Boulevard in their specially decorated wagons, bicycles, and strollers while donning their best pirate attire. The Stroll begins at Howard Avenue and ends at Rome Avenue.

How much is Gasparilla entrance? ›

$2 pedestrians, bicyclists, extra passengers, passengers in vehicle with holder of Annual Individual Entrance Pass. There is a toll to access Gasparilla Island on the Gasparilla Island toll bridge. For fees, please contact the Gasparilla Island Bridge Authority at 941-697-2271, ext. 1.

Are backpacks allowed at Gasparilla? ›

Glass containers are also not allowed along the route. The city says on its website that all bags and backpacks are subject to search. Prohibited items include: Outside food or beverage (the Gasparilla Pirate Fest website states there are over 100 food, beverage and novelty vendors located throughout the event)

How do you become a Gasparilla pirate? ›

You must submit, in writing, on organization or corporate stationery, a request for consideration for entry in the parade, stating the name of your group or organization and how you wish to participate, i.e., float or specialty unit.

Is Gasparilla fun? ›

It's crowded, it's fun, and it's something you definitely need to be prepared for. Here are a few things to expect at Gasparilla next year. Gasparilla typically kicks off around 11:30 a.m. with the Pirate Invasion.

How much is parking at Gasparilla? ›

There are many city parking lots and on-street parking close to the start and finish line. Expect to pay $10 for all-day parking with no in-and-out privileges.

Is Boca Grande and Gasparilla the same? ›

Boca Grande is a small residential community on Gasparilla Island in southwest Florida. Gasparilla Island is a part of both Charlotte and Lee counties, while the actual village of Boca Grande, which is home to many seasonal and some year-round residents, is entirely in the Lee County portion of the island.

Who lives on Gasparilla Island? ›

Numerous sports, showbiz, and political luminaries such as Katherine Hepburn, Harrison Ford, George H.W. Bush, Jason Garrett, and Tom Brokaw have all been known to rent or own vacation homes on the low-lying barrier island.

Who owns Gasparilla Island? ›

The resort employs more than 325 people on a seasonal basis and continues many of its original traditions, including afternoon tea during Social Season. The Inn is presently owned by the William Farish family. William Farish is a former United States Ambassador to The Court of St.

What celebrities are in Boca Grande? ›

It may have hosted Henry Ford, Thomas Edison, Audrey Hepburn, the George H. W. Bush family and more recently Nick Saban and Tucker Carlson, but the elite island of Boca Grande is still a place where regular folks can have a grand Old Florida experience.

What is the most expensive house on Boca Grande? ›

A Mediterranean-style mansion on 130 feet of Gulf-front at 161 Gilchrist Ave., the toniest street in the exclusive old-Florida island community of Boca Grande, sold for $7.4 million this week.

Why is Gasparilla called Gasparilla? ›

Named for pirate Jose Gaspar, who terrorized the coastal waters of West Florida during the late 18th and early 19th centuries, Tampa's annual Gasparilla celebration begins with the Gasparilla invasion.


1. The True Story of Gasparilla~ Mythology from Home
(Tim the Historian)
2. The history of Gasparilla: Tampa's unique pirate invasion fest
(10 Tampa Bay)
3. The Legend of Gasparilla
(Charlotte County Community Services)
4. The history of Gasparilla: Tampa's unique pirate invasion fest
(10 Tampa Bay)
5. Treasure Hunters May Have Found José Gaspar's Pirate Vessel In Florida | Expedition Unknown
(Discovery UK)
6. What is the Gasparilla Pirate Festival + Parade ??? 🏴‍☠️ Tampa Traditions | MELANIE ❤️ TAMPA BAY
(Melanie Loves Tampa Bay)


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