Useppa Island

And then there's Useppa Island, a mellow little resort in Pine Island Sound, just north of Captiva Island. It's been, sporadically, a hotel resort since 1896, and declassified documents revealed the CIA used it for secret training of officers for the planned and aborted Bay of Pigs invasion of Cuba in April 1961.

This island's name has a legend about it - another one of those forced, reverse-engineered ones made up years after the fact because humans simply can't abide the vacuum - which states there once was a girl named Useppa who was kidnapped from her home in Havana, Cuba and held prisoner on this island by Gasparilla the Pirate. Supposedly he beheaded her, and of course, this leads to the story that people say that to this very day, you can sometimes still see her headless ghost walking along the beach. That is, if you've had nine Fuzzy Navels on an empty stomach.

The same story, by the way, is the basis for the folk-etymology name for Captiva Island, where Gaspar is said to have kept scores of women held captive for ransom and such. This guy must have had women stashed on every island. And it doesn't help the believability factor when you realize the exact same stories are told about another pirate, Black Caesar.

The real origin of the island's name is most likely a series of misheards going back to when it was referred to as Josefa Island in an 1838 document. From there, the name got mangled into "Giuseppe Island" on an 1870 census and "Useppi" in 1875, finally arriving at the spelling of "Useppa" as so called by the Smithsonian Institution in 1882.

Then again, some have suggested the original "Josefa" name comes from the princess daughter of Martín de Mayorga, Viceroy of New Spain from 1779 to 1782, and that she was indeed killed on this island. This almost lends some credence to the Gasparilla story... except it doesn't. And there's still another haunting legend on Useppa Island, one that says reported sightings of the ghosts of the Calusa Tribe are common. How some tourist from Nova Scotia would know what a Calusa looks like, I don't know. But they did encamp on the island in antiquity. So there.

But never mind all that. Useppa Island is a lovely place for a getaway, with luxurious lodging and dining for those who want to get away from it all a little further than Captiva.