“Sloppy Joe’s was Papa’s favorite haunt. Barefoot, with his shorts cinched with a rope and wearing a ragged T-shirt, he would make the trek down Duval after a six-hour writing jag . . . Sometimes Hemingway came alone and sat at the end of the long, curving bar, making notes. Josie Grunts (as Ernest called him) would be there, and Skinner, the 300-pound bartender, would fix a ‘Papa Dobles’: 2 1/2 jiggers of white Bacardi rum, the juice from half a grapefruit and two key limes, and 6 drops of maraschino. Skinner, ‘the giant black handyman with his Louis Armstrong smile, could always cadge a drink by squatting under the piano and lifting it off the floor for a few seconds.’ He was Joe’s regular drinkmaker and worked at Sloppy’s until he died in 1949.” —Sloppy Joe’s Bar: The First Fifty Years, 1983, Sharon Wells
“I went down to Key West because I love swimming . . . It was January, and I had to go someplace where I could swim in the winter so I came down here because it was the southernmost point, and I was immediately enchanted by the place. It was so much more primitive in those early days.” – Tennessee Williams (1911-83), quoted in Pop Culture Florida (2000) by James P. Goss
Two of Ernest Hemingway’s uncashed royalty checks hang on the wall at Sloppy Joe’s Bar.
Jimmy Buffett’s Key West anthem, “Margaritaville,” reached No. 8 on the Billboard charts in 1977.
Robert the Haunted Doll resides at the Fort East Martello Museum & Gardens (don’t take his picture unless you ask permission!).
The Conch Republic Independence Celebration each April celebrates the island’s “secession” from the United States in 1982.
The Ernest Hemingway Home and Museum is home to approximately 40-50 polydactyl (six-toed) cats.
According to legend, Jimmy Buffett’s first Key West gig was at the Chart Room Bar.
The Key West Aquarium began construction as part of the Works Progress Administration program and opened in 1935.
At Sloppy Joe’s Bar hangs a Cuban record blue marlin (weighing 569 lbs.) caught by author Phil Caputo (A Rumor of War).
Set in Key West, Thomas McGuane’s 1973 novel, Ninety-Two in the Shade, was made into a movie in 1975 with Peter Fonda, Warren Oates and Margot Kidder.
Ernest Hemingway once dubbed Key West the “St. Tropez of the poor.”
Jimmy Buffett first arrived in Key West in November 1971 with singer and songwriter Jerry Jeff Walker (“Mr. Bojangles”).
Ernest Hemingway had the first residential pool built in Key West in the late 1930s at a cost of $20,000.
Duval Street is known as the “World’s Longest Street” since it runs from the Atlantic Ocean to the Gulf of Mexico.
The Harry S. Truman Little White House is billed as “Florida’s Only Presidential Museum.”
The Green Parrot Bar is billed as “A Sunny Place for Shady People.”
The Key West Cemetery features quirky inscriptions such as “I Told You I Was Sick” and “Devoted Fan of Singer Julio Iglesias.”
Dry Tortugas National Park lies nearly 70 miles West of Key West and is accessible only by seaplane or boat.
“Our adventure lasted the entire day. We stopped at every watering hole, beer joint, bait shop and catfish bar between Key Largo and Key West. I had been in most of them before. It was ‘Hello’ at the door, my favorite beer opening as soon as we stepped inside. And soon, they knew Jimmy too. Finally, we wheeled into Key West and thrust Buffett toward the sand and the ending of the day. We watched his face blush with orange and his blue eyes go sunset. Buffett filled his lungs, but he wasn’t smelling a cheeseburger in paradise. He was inhaling the salt air of his childhood, hearing music in the distance, tasting shrimp in his dreams. Jimmy had his face in the front door, and the future was saying come on in.” —Jerry Jeff Walker, Gypsy Songman, 1999
“What’s it all about? Well, booze, for starters. But breathtaking sunsets, rich history, live music and livelier folks are quick to fill out this one-of-a-kind-Key Largo landmark.” – Caribbean Club Website
Billed as “one of the last relics of Old Key Largo,” the Caribbean Club (Mile Marker 104 Bayside) first opened in 1938 as a “poor man’s fishing retreat” and has been locally owned and operated since 1963. The Caribbean Club, which is filled with memorabilia from the 1948 film Key Largo (exterior shots from the movie, which starred Humphrey Bogart and Lauren Bacall were filmed here), features live music Thursday through Sunday nights, daily happy hours and amazing sunsets.