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Who Tours SW Florida

Who Tours Southwest Florida?

Ever wonder who tours the Gulf islands that make up Southwest Florida between Fort Myers and Sarasota?  These barrier islands are a favorite of photographers and film producers but Gasparilla Island is the "secret island" that former presidents, dignitaries and celebrities like to sneak away to because the island residents maintain a very low key attitude regarding celebrity and fame. They love to leave the "off island" world behind to come rejuvenate and recharge their senses on these small untouched islands where Florida seems unplugged from the modern world!

So, who tours Gasparilla Island, Manasota Key and Cabbage Key, Florida?

A few we know about have last names like the Campbells, the Kelloggs, and the du Ponts. Just to the north of Gasparilla island, you might wonder who tours Manasota Key?  The late great Donna Summer is only one of many celebrities that had a vacation home there.  Ever heard of a remote island called Cabbage Key?  Jimmy Buffet is another celebrity who tours this tiny island.  In fact, it was there he wrote the song "Cheeseburger in Paradise."  Another famous person who tours Gasparilla Island is actress Katharine Hepburn!  Several winters in a row, Katharine Hepburn leased the house that Mr. Campbell now owns in Boca Grande. Former President George H. W. Bush is another  of many famous people who have spent several winters on Gasparilla Island.  Locals still buzz about President Bush's wife Barbara and their dog Millie, along with their spirited grand-daughters Barbara and Jenna. Britt Hume of FOX News also frequents Boca Grande.  All visitors, whether famous or not love that Old Florida feeling of stepping back in time to a place where there are no restaurant chains, no high rises, no stop lights and no large grocery stores.  Without a doubt, entertainers, artists and ambassadors all like to mingle on Boca Grande right alongside of us so-called "regular folk!"

Besides famous people, who else tours our islands like Cayo Costa, Cabbage Key, Captiva and Pine Island?

Most are just average, everyday people that are drawn to nature.....people that love seclusion....people that like to snorkel in the cerulean waters usually only found down in the Caribbean.  People attracted to our islands also love to book yacht charters to fish and cruise around the islands.  It is not uncommon to see a rich and powerful C.E.O. become best buddies with local charter boat captains.  Our yacht charter from Englewood, Florida to Captiva Island is our most popular itinerary. It includes a stop in Boca Grande, lunch in Cabbage Key and perhaps an overnight stay on Captiva Island at Tween Water's Resort.  Most like to tour the mangroves teaming with a wide variety of tropical flora and fauna along with copius marine life including dolphins, manatees with swarms of bait popping the water virtually everywhere!

It is usually on these tours that we get to tell the most fascinating tales about who toured our islands in the past ..... infamous pirates such as "Black Caesar" "Jose Gaspar" and "Blackbeard" to name a few....along with a few ghosts!

Pine Island, adjacent to Captiva and north of Sanibel is where "Black Caesar" supposedly stored some of his stolen treasures which have yet to be found. Henri Caesar turned to piracy in 1805, during a slave revolt in Haiti. He then high-jacked a ship, along with a boat load of slaves and soon began raiding Spanish trade ships.  After a war in 1812, British warships began patrolling the waters between the Bahmas and Cuba curtailing Caesar's pirate raids. Because of the presence of the British warships, Caesar had to push his pirate pack back up north to the Gulf of Mexico. Some historians claim Caesar has between two and six million dollars of treasure stashed somewhere on Pine Island. In fact, several of the very old trees on this island still bear mysterious pirate markings discovered by a man named Juan Gomez.  However, no one has been able to decipher them though some believe the markings identify another island called Round Key as the location of the treasure.

While in Florida, Caesar came to know another infamous pirate by the name of Jose Gaspar, familiarly known as Gasparilla (and of course, Gasparilla Island is named after him!)  Gaspar was no doubt a rebel but was also from an aristocratic affluent Spanish family.  It was because of those roots that he always considered himself to be a "true gentleman" though legends often say the opposite.   Many legends abound surrounding Jose Gaspar.  However, we do know a few things about him that were facts. Born in 1766, he was short of stature, was a brilliant navigator, a fine swordsman, a man of great intelligence and ambition.  Eventually, he somehow worked his way into a high position in the court of King Charles III. Unfortunately, and though quite commonplace in political situations (then and now!) other members of the high court possibly became jealous of his success and so they plotted against him, convincing the king that Jose was guilty of treason.  This resulted in his wife and infant son being murdered and his home being burned to the ground while he was out to sea.  Orders were given by the king for his arrest after he returned from sea back to Spain.  Somehow, one of Jose's close friends managed to get word to him, so he never returned to his homeland.  It is said he vowed to "henceforth become an enemy of Spain."  It is worth noting here that, he did not say he was going to become a pirate, just an enemy of Spain.  However, another legend holds that at the age of 12, Jose kidnapped a young girlfriend for ransom.  The parents of the girl knew it was some kind of a scam to extort money and turned him over to the authorities. After getting caught, he was given two choices: either go to jail or sail with the Royal Spanish Navy so, he chose to set sail.  Yet another story maintains that during his years in the high court, he was accused of stealing royal crown jewels by the daughter of the King (his jilted lover) and at that point, he fled from Spain for good.

No matter which story you believe, Gaspar eventually commandered the Spanish Naval ship "Floridablanca" and sailed to Southwest Florida to begin a whole new life for himself.  He also vowed to attack any ship that was flying a Spanish flag and during his 38 year rampage, he attacked and plundered over 400 ships. Moreover, during his revenge on Spain, he abducted over a hundred women from the Warships, keeping the women for ransom or as personal concubines.  He, along with Blackbeard the pirate who had hailed from North Carolina took women from wealthy families and held them on Captiva Island until some extremely hefty ransoms were paid.  However, although Blackbeard was among the most feared pirates, legends say that he never harmed or killed any of his captives, unlike Jose Gaspar!  Very close to Captiva Island lies a private island known today as Useppa Island. This tiny island is named after the girl with who was kidnapped from Havana, Cuba and imprisoned on Captiva island by the pirates.  It is said that Gaspar was very smitten by the young lady and took her to the small island in order to court her.  Unfortunately, she did not return his affections so he beheaded her. To this day, people swear they still see her headless ghost walking along the shore of Useppa Island.

During his time in our Florida coastal waters, Black Caesar wanted to form a partnership with Jose Gaspar. Gaspar itinitially treated this proposal with great contempt though eventually he compromised and permitted Caesar to build a camp on Sanibel Island, south of Pine Island and adjacent to Fort Myers. Gaspar's main headquarters in Boca Grande was well-fortified with cannons, but he was very calculating so realized the additional protection on Sanibel would provide him with more safety to the south. Caesar's camp, which was basically a series of palm thatched huts guarded by packs of mangy dogs was a marked contrast with Gaspar's mansion in Boca Grande which was heavily staffed with maids and servants.Although Black Caesar was alleged to have concealed at least two million on Sanibel Island (jewels, silver and gold coins) some historians have estimated this plunder to be worth as much as six million dollars!  However, this is quite difficult to substantiate because the treasure has never been recovered.

In 1891, Gaspar’s reign of terror ceased after an attack on a British ship that didn’t quite go according to plan.  Ironically, Gaspar had finally decided to give up piracy but somehow couldn't resist the lure of "just one more" wealthy British ship that was just offshore.  Seeing the chance for one last score, Gasparilla took off in pursuit of what he thought was going to be an easy target.  But, just as the ship came within range, the British ship dropped its colors and ran up the flag of the United States!  Instantly, dozens of huge cannons were revealed from its deck and they fired directly on Floridablanca.  Jose Gaspar had fallen into a death trap because the seemingly helpless British ship turned out to be the U.S. Navy’s warship – the USS Enterprise. 

Though a fierce battle ensued, the end was inevitable.  The American cannonballs repeatedly imploded the  Floridablanca’s hull and eventually shattered her masts.  The Floridablanca was sinking as the USS Enterprise approached to finish the military task at hand.  Rather than face life in prison, Gaspar rushed to the bow of his ship yelling “Gasparilla dies by his own hand, not the enemy’s!”.  With that, he quickly wrapped the anchor’s chain around his waist and plunged into the dark waters, instantly disappearing below the waves. The remainder of his crew were either killed or captured.  Those captured were later tried as pirates and executed in New Orleans. On that fateful day, Gaspar finally met his match!  The men that were captured were tried as pirates and were later executed in New Orleans.

So where is Gasparilla’s Treasure?

It just so happens that during the time the British merchant ship (USS Enterprise) was spotted, Gasparilla and his pirate crew were in the process of dividing up all the spoils. The treasure from so many years had been loaded into twenty large chests, each one filled to the brim with gold and jewels. The story is that these chests were actually sitting right out on the beach when the merchant ship was spotted.   

Gasparilla chose ten of his most trustworthy men with those treasure chests and then rushed in with the rest of his crew in pursuit of the merchant ship.  Those ten men supposedly witnessed the battle with the USS Enterprise while sitting a distance away onshore.  As they watched the Floridablanca go down, they loaded the treasure chests onto a longboat and quietly slipped away, unnoticed, up the Peace River to a place called Spanish Homestead.  At that time, Spanish Homestead was owned by a woman named Lady Boggess. The pirates reportedly bribed Lady Boggess with part of the treasure in exchange for not divulging their location to the Americans soldiers if they pursued them to the area.  Apparently, the pirates were not pursued  by U.S. Naval forces and they escaped into the Florida swamps unnoticed. The pirates spent several days burying the remainder of the chests in different spots in the swamps and along the streams around the Peace River.  Afterwards, they burned their longboat, disappeared and were never seen again. Near the Spanish Homestead, approximately $300,000 in gold coins was found many years later....though the rumor is/was that this was only a small part of Lady Boggess’ hush-money.  Regardless, the remainder of an estimated $30 million dollars in gold and jewels still remains undiscovered somewhere along the banks of the Peace River.  

As tour guides here, we are constantly asked who tours these islands and all about the pirates and treasure.  Whether it is fact or fiction, it definitely makes for some very interesting stories on our yacht charters around these islands.  Ghost stories and sightings are commonly reported on many of these remote islands that are still not well known...and many are unnamed.  Scuba diving and metal detecting are among the favorite activities of both visitors and locals alike! Bookmark this page at and book a yacht charter or a boat rental with us for your next Florida vacation.  Who might get lucky and uncover some treasure and though we can't guarantee this, and while we can't guarantee you will see any celebrities, we can guarantee you will see a wide variety of magnificent birds and dolphins along with some of the most dramatic sunsets you have ever witnessed. 

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