FMB InsiderThe Public Record

Tall Tales

Stories told — but not proven

Every island collects legends, and Fort Myers Beach has good ones: pirates, buried gold, rum-runners in the moonlight. We love them enough to tell them — and we respect you enough to be clear about which parts history can actually confirm. Everything here is a story people really tell. What each one isn't is verified fact, and we say so.

How to read this page: the colored label on each story is our honest verdict — from “almost certainly a myth” to “rooted in real history.” For the verified island story, see the history page.

The pirate José Gaspar (“Gasparilla”)

Our verdict: Almost certainly a myth

The story is irresistible: José Gaspar, “the last of the Buccaneers,” a Spanish pirate who supposedly ran a base in southwest Florida around 1800, raided the Gulf, and buried fortunes along these islands. His name is stamped on Gasparilla Island up the coast, and Tampa throws a giant pirate festival in his honor every year.

Here's the honest part: historians have found no evidence he ever existed. There is no trace of him in Spanish or American archives and no physical evidence of his presence in Florida. The first printed Gaspar story appears to have been commissioned around 1900 by a railroad to lure tourists to a new resort hotel. In other words, one of Florida's most beloved pirates was very likely an advertising campaign.

We include him because the legend is real even if the pirate isn't — and because it's a perfect reminder to check the source before repeating a good story.

Buried treasure in the shell mounds

Our verdict: Told for generations — never found

Where there are pirate legends, there are treasure legends. Stories of Spanish gold and pirate caches hidden in the Calusa shell mounds and along the barrier islands have circulated southwest Florida for over a century — fueled, understandably, by the fact that Spanish coins really did change hands here during the 1800s cattle trade at Punta Rassa.

But real Spanish coins paying for real cattle is a very different thing from a buried pirate hoard, and no such treasure has ever been documented as found on Estero Island. File this one under “fun to imagine while you're shelling.”

Rum-runners in the Prohibition years

Our verdict: Rooted in real history — island specifics unconfirmed

During Prohibition (1920–1933), Florida's maze of mangrove islands, hidden passes, and proximity to Cuba and the Bahamas made the Gulf coast genuinely notorious for rum-running— that part is solid history across southwest Florida. Locals love to say Estero Island's quiet coves and canals played their part.

We haven't yet found a rigorous, sourced account tying specific rum-running exploits to Estero Island itself, so we flag it honestly: plausible and regionally true, island-specific details unconfirmed. If you have a documented local story, we'd love to see it.

Know a good one? Offshore powerboat races, old fish-house characters, a hurricane that someone swears changed the shape of the pass — Fort Myers Beach is full of stories. If you can point us to where a tale was told (a book, a newspaper, a named old-timer), send it our way and we'll research it and add it — with the same honest labeling.