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

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

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

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

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

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

A monument celebrating the idea of reaching inaccessible places.

This small Key West museum is packed with dozens of artifacts that illustrate the life of the iconic playwright.

The island residents are known for taking their quirky sense of humor with them to the grave.

"We Seceded Where Others Failed."

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

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

Bat house that has only ever housed bat for one night; they all flew away and never came back.

A nude beach alongside a washed-out road.

A mysterious castle built as a monument to lost love.

A tribute to Ponce de Leon's supposed quest for eternal youth.

On Hilton Head Island this bronze King of the Sea rules all things briny—and lets you know if you’re late for lunch.

The remains of a chapel created for convenience.

This South Carolina water tower is an icon of the city of Walterboro, but it also once served as the county jail.

One of the oldest living oak trees in the Southeast.

A quirky Poe-themed joint on an island keen to celebrate its overlooked connection to the famous writer.

Charleston's historic city jail once held everyone from pirates to Civil War POWs.

Once the most flame resistant building in the country, the South Carolina Historical Society building was almost burnt down in a fire.

South Carolina's last remaining slavery auction house is now a museum devoted to its own tragic history.