Weird Festivities in Florida's Crazy Keys

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Isolation can cause people to go a little stir crazy. That’s the only logical explanation for the Florida Keys. For our last Florida entry of the Strange States series, let’s take a look at some of the fun, but slightly off-kilter, festivities that can be had on the islands.   

The Conch Republic Rebellion


When you get off the plane at the Key West International Airport, don’t be confused by the sign that reads, “Welcome to the Conch Republic.”  No, you didn’t get on the wrong flight, but you might be surprised you’re (in a way) no longer in the United States.

In April 1982, the U.S. Border Patrol set up a roadblock and inspection point just north of the Keys on U.S. Route 1, the main highway that connects the islands to the mainland. The Patrol stopped every car, searching for drugs and illegal immigrants, both of which were said to be smuggled into the country on the highway. The roadblock was a huge inconvenience, causing traffic jams that spanned miles, and seriously impacted the tourism that the Keys so heavily relied upon.

The City Council of Key West attempted to have the roadblock removed, but to no avail. And so, since the roadblock was essentially creating a new American border north of the Keys, the Council—with tongue planted firmly in cheek—declared the islands an independent country on April 23. Since the residents of the Keys often called themselves “Conchs,” the newly established sovereignty became known as The Conch Republic, with the motto “We Seceded Where Others Failed.”

After their secession, the Conch Republic declared war on the United States by hitting a man dressed in a Navy uniform with a piece of stale Cuban bread. A few moments after this horrific sign of aggression, the Republic officially surrendered to the same Naval officer, and then asked for $1 billion in foreign aid (their request was denied). The event, even in jest, caused such a worldwide media stir that the roadblock was soon removed.

Always looking for a way to promote tourism in the Keys, you’ll find Conch Republic memorabilia in every souvenir shop on the islands. Trinkets include Conch Republic flags, t-shirts, passports, and even coins, which are accepted currency in some local businesses. In addition, to honor their brief taste of freedom, the people of Key West set aside 10 days every April to celebrate their independence with a huge festival filled with parties, the “World’s Longest Parade” down U.S. 1, as well as the “World’s Longest Bar Stroll,” a pub crawl that goes from the Atlantic to the Gulf in one afternoon.

Underwater Music Festival

Unless you’re a little mermaid who wishes she could be part of someone else’s world, chances are listening to music underwater just sounds like a muffled mess. But that hasn’t stopped music-loving divers from gathering every July for 29 years at the Looe Key Reef to be a part of the Lower Keys Underwater Music Festival.

So how does one even hold a submerged music festival? Boats floating on the surface lower specially-designed speakers into the water and blast out tunes played by WWUS 104.1FM, a local radio station. The music usually has a nautical theme—The Beatles’ Yellow Submarine is always on the playlist—but they also play more unusual fare, like blue whale songs. But the highlight of the show is the tribute performance to a real singer or band, featuring divers pretending to play handmade instruments like a “manta-lin,” a “clam-bourine,” or a “trom-bonefish.”  This year the headlining “band” was the Rolling Crab Stones, starring “Mick Jawfish” and “Keith Pilchard,” singing their hits “Jumping Jack Fish” and “HonkyConch Woman.” 

Although it’s all in good fun, the festival also promotes an environmental message. Throughout the show, PSAs educate divers about the importance of protecting the Florida Key Reef System, the only living coral reef in North America.


If the only time you can take a vacation is in the fall, Key West has you covered with FantasyFest, which is like a Halloween costume party, Mardi Gras, and Gay Pride Parade all rolled into one.

For 10 days in October, the streets of Key West are flooded with ghouls, vampires, zombies, and ghosts in numerous, family-friendly, costumed parades, 5K races, and outdoor festivals. But you can also leave the kids at home and head to more risque events like the Tighty Whitey Party starring the Men of Labare (as seen in Magic Mike), or the Wild, Wild, Key West Party where cowboy boots and hats are among the only suggested attire. You could also hit up the ABC (Anything But Clothes) Party, stop by the Dungeon of Dark Secrets and Fetishes, and frolic in the pool, hot tub, or dance floor full of foam at the Bourbon St. Pub Adult Entertainment Complex. 

Now those are some vacation photos your friends will want to see...

Sundown Celebration

If you can’t make it to one of the other Key West fests, it’s not a problem, because there is literally a festival every day of the year—the Sunset Celebration at Mallory Square Dock.

The Sunset Celebration began in the 1960s as an unorganized gathering of about 40 hippies who would take a hit of LSD, then head down to the docks to watch the sunset every night. As word of the tradition got out, entrepreneurial sorts set up temporary booths on the pier to sell jewelry, t-shirts, and other handmade goods, before disappearing as the crowd dispersed after dark.

By 1984, the nightly farewell to the sun had become a hip social scene, and bigger crowds meant more vendors. When nearby businesses began to complain about the pierside booths, the City of Key West threatened to shut the whole thing down. In response, a small cadre of artists formed a non-profit group called the Key West Cultural Preservation Society in order to legitimize the nightly festival and help keep it alive.

Today, you can still find plenty of artists selling paintings, sculptures, and jewelry every night on the pier. But you can also watch entertaining acts like Dominique the Catman and his specially-trained “flying house cats,” who jump through hoops and perform other tricks for the crowds. Or there’s Will Soto, one of the founding members of the Cultural Preservation Society, who’s been performing death-defying high wire juggling acts for over 20 years. You might also catch Dale the Sword Swallower, Mark Riggs, who juggles fire atop a 10-foot “Suicycle of Death” unicycle, straight jacket escape artist Casey Moore, Dennis Riley “The Southernmost Bagpiper,” and Checkers Mallory, a guy who runs around in a checkerboard head-to-toe bodysuit doing...something.  No matter what your interests, there’s something for you at the Sundown Celebration, making it a can’t-miss event if you visit the Keys.

And that's a wrap on Florida ... for now! Check out all entries in the Strange States series here.