This kitschy tavern is also home to rare early editions of "Treasure Island."

Disney World's very first waterpark is now an abandoned ruin being reclaimed by the swamp.

Mariners once used this prehistoric landfill as a navigational landmark.

The sign that drew attention to a young boy's cucumber stand is now the name of his fruit superstore.

The highway's southernmost spot is a beloved local attraction.

Electrical pylon in the shape of Disney's beloved mouse.

This isolated airport in the middle of the Everglades sees more alligators than planes.

The walls of America's oldest masonry fort famously "swallowed" cannonballs.

A historic presidential getaway on the continental United States' southernmost island.

Leave it to Key West to drop a real-live drag queen instead of a ball to mark the arrival of the New Year.

"We Seceded Where Others Failed."

An idyllic swimming pool tells the tale of Hemingway's trouble with women.

The birthplace of American international flight service has been turned into a celebrity's microbrewery.

Intertwined, interspecies trees which locals believe can grant boons to lovers.

A monument celebrating the idea of reaching inaccessible places.

An 18th-century Spanish watchtower made entirely of seashell and concrete.

Florida's oldest bar was once a morgue, complete with a hanging tree and gravestones.

A luxurious 1880s hotel with its fair share of Tiffany stained glass, Edison electricity, and of course, ghosts.

This legendary "evil" doll has been haunting the citizens of Key West for over 100 years.

The former home of the Nobel Prize-winning American writer is now home to dozens of six-toed cats.

Disney's abandoned animal island is now an overgrown ruin that was almost the coolest attraction ever.

These remote Florida islands have a history of sea turtles and sunken treasures, and one of the world's largest coastal brick fortresses.

The last holdout of a pre-Civil War rebel who took the matter of slavery into his own hands.

One day a year it is legal to jump off of this astoundingly tall bridge that spans an Appalachian gorge.