A sanctuary for sickly, stray, or wounded donkeys.

This huge pile of volcanic boulders hides a stunning network of secret grottoes.

Rumored to be the famed pirate's lookout tower, this historic stone structure is now just watching for tourists.

This small fort played a huge role defending Puerto Rico’s capital city.

This colorful gate stands as an entrance to the walled city of Old San Juan.

Send a postcard while vacationing with Satan.

The capital of the Cayman Islands is a center of offshore banking, but gets battered by blistering hurricanes.

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

A historic landmark and museum filled with curious objects representing the history of Key West.

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

The museum chronicling a treasure hunter's dream, fulfilled.

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

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

A small poultry graveyard in the courtyard of a popular Key West watering hole.

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

"We Seceded Where Others Failed."

A monument celebrating the idea of reaching inaccessible places.

Island ghost town detailing Flagler's folly in building the Overseas Railroad.

This 140-year-old beacon off the Florida Keys marks the wreck of a Navy ship that once roamed the Caribbean hunting pirates.

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

Former villa and estate of James Deering developed to preserve native tropical forests.

In a time before lifeguards, this house was a sanctuary for the shipwrecked.

Possibly the most beautiful carillon in the world, set atop Iron Mountain in Florida.

A haunted hill that supposedly defied gravity.