Let A Trip To The ‘Conch Republic’ Soothe Your Weary Soul This Fall

Do you know the story of the Conch Republic? It’s a great little yarn from the weird-ass ’80s — an odd moment in time when America’s renegade spirit collided with an overzealous government. It also tells you pretty much everything you need to know about Key West, Florida, where the whole saga went down.

The gist of the story is this: In 1982, concerned about drugs and immigration, an incredibly restrictive roadblock was set up on U.S. Route 1, linking the Florida Keys to Miami. The move proved catastrophic. It discouraged tourism and stymied locals. But more than that, it operated on a metaphorical level — offending the fiercely independent sensibilities of those living in the lower 48’s southernmost settlement.

In order to get the attention of the Federal Government, after written complaints went unanswered, mayor Dennis Wardlow and the Key West City Council decided to secede from the nation. They called themselves the “Conch Republic” and named Wardlow their Prime Minister. Sound ridiculous? The “Conchs” were just getting started. Next, they declared war on the U.S. (by breaking a loaf of Cuban bread over the head of an actor pretending to be a Navy officer), then surrendered to that same officer exactly one minute later. There were no casualties. Except the bread.

Ready for the kicker? The protest worked and the roadblocks were removed.

In 2016, that story — in which everyone was generally playful and a problem was solved in an oddball way — seems like a folk tale from a bygone era. And perhaps those days really are behind us. I don’t want to be in the business of talking wistfully about the past, considering that basic human rights around the country were in a much worse place. But that little slice of nostalgia does come naturally to mind as our brutal election cycle grinds to a finish. Especially since someone will surely be grumbling about secession come November 9th.


My girlfriend, Nikta, and I drove toward Key West with Boyz II Men’s “I’ll Make Love To You” playing on the radio. We’d flown in from Southern California, partied for a night in Miami, eaten a 3am Cuban sandwich at some famous diner, crashed at a grungy hostel, and tucked into breakfast by 9am. All things considered, belting out Boyz II Men felt like a good omen.

More good omens arrived quickly on the heels of the first. After an hour of driving down the Keys, I needed a nap. A short night on a mattress covered in plastic was taking its toll. I hooked a turn off the main road, drove aimlessly for a few minutes, and found an abandoned lot right on the water. We probably only slept for about a half hour, but it was that special brand of high quality sleep where every minute counts for five — the sun was out but it wasn’t too hot, a light breeze played across the grass, we dangled our feet off the sea wall, and Nikta had her head on my chest. That’s power sleep, right there.

When we woke up, my first thought was, “Wouldn’t it be cool to see a manatee?” This was answered by the quiet voice of reason. Right before I’d left, a Floridian went out of her way to tell me, “Don’t get your hopes up about manatees, they’re more rare than you probably think.” And yet, seconds later, as if on cue, a gray-blue sea cow rose to the surface. It was grazing just a few feet from our spot. I knew, right then, it was going to be one of those special trips where everything seems to unfold like a movie starring Joseph Gordon-Levitt.



We pulled into our hotel by midday. We’d booked in at The Gates, a mile or two north of the city center, for a few reasons that were crucial to our personal needs: 1) the property has a pool, 2) they give you free bikes, 3) there’s actually an on-site food truck specializing in pulled pork. Every human on this planet has their own matrix of what sounds good to them when traveling, and it may very well be a different grouping of factors for each trip — but for this trip, pool, pulled-pork, and pedal bikes described our exact sweet spot.

After a dip, we rode bikes into town. Key West’s main drag, for anyone who hasn’t been, is infused with that mystical air of people who feel quite certain that they’re living the good life. I’ve seen it before in New Orleans, Portland, and Costa Rica. The locals aren’t bothered by the tourists and the tourists are somehow managing to be un-bothersome. It’s as if everyone is walking in a dream-state and to be either annoying or annoyed would mean you’d have to snap back to reality.

Or maybe it’s just because everyone was drunk. Because seriously, everyone was drunk. Drinking in Key West isn’t treated like an indulgence, or even a pastime, it’s treated like an endurance sport and most of the island is in constant training. Forget the hyper stylized L.A. clubs where you have to wait in line for a month to be served at a bar made of brushed aluminum, in Key West bars are “water holes” — dives where they staple bras to the ceiling and serve Margaritas in plastic cups. Literally every place you go has live music.

Nikta and I found a bar we liked, Captain Tony’s (where Hemingway used to hang), ordered a pitcher of margaritas, and played a cutthroat Uno while a guitarist riffed on classic rock covers. We rode back to the hotel around 1am, fortified by giant, greasy slices of pizza.

If that paragraph doesn’t resonate for you, Key West is probably a hard pass.



“I think the thing that ties us all together here is the sunset. Because people who live here know it’s never going to be the same sunset. So you look forward to it. Every night, I get on my bicycle, go to the boat, or go any point on the island and watch the colors.”

Those are the words of Paul Menta, a man who just might make the world’s best Key West case-study outside of Jimmy Buffet. Menta hails from Philly — and retains that Northeast edge — while flourishing in a way that is completely unique to his adopted home. He kite boards professionally, he’s the chef at a restaurant, he owns a rum distillery, and yet he finds time to spearfish, surf, and watch the sunset from his boat almost nightly.

On top of all of this, Menta acts as an ambassador for the island — a shining example of Key West’s private label blend of independence, laid back attitude, and exultant weirdness. That weirdness is hard to miss, I’ve never been to a place where the phrase, “That guy, he’s a character,” could be used to affectionately describe such a high percentage of the populace.

“All of us, we’re all odd balls,” Menta explains. “When you get into an area, where everybody’s odd, it becomes the new normal. You can relax. You can take a deep breath, and know that you don’t stand out. You’re just another person, one of the many odd balls — crazy, creative people, who will inspire you. But, you’re also nothing special.”

If you saw that on a tourism poster, wouldn’t you book a ticket immediately? Wouldn’t you long to mix it up with the scalawags and brigands that draw to the Conch Republic like moths to a lantern? Actually spending time with Menta only made the whole proposition that much more attractive. He took Nikta and I out on his boat, to a sandbar where we dropped anchor, popped a bottle of wine and watched the sunset. Sure, for us this was a vacation, but for Paul and his girlfriend it was just an average Wednesday.

Later, he took us for dinner at The Stoned Crab — where we had a bucket of Gulf Stone Crab claws that I hope to never forget. For the uninitiated, these massive claws are removed from the body and the crab itself is left behind; the claw regenerates, making it the ultimate sustainable fishery (Monterrey Bay agrees). Menta prepared the claws by putting them in a pretty simple seafood boil then serving them on ice. I’ve never had any lobster that could hold a candle to the snowy white claw meat.

Later, we went to Menta’s rum distillery for a late night tour. As our host shared his process of experimentation, I felt a deep upwelling of jealousy surge through me. I’ve always wanted the Jimmy Buffet line, “Yes, I am a pirate. A few hundred years too late…” to apply to me. Menta embodies it better than anyone I’ve ever met.


If I was tapped to redesign the Conch Republic’s flag, I’d probably go with a plastic margarita cup, a sunset, and a jet ski. These, from what I saw, are the island’s three primary icons. In one week, Nikta and I watched the sunset every night, drank every night, and rode jet skis three times. Usually, I cringe at being the tourist buzzing around on a Kawasaki, but riding a jet ski is Key West’s ultimate “When in Rome…” activity. Also, who wants to be the guy who turns down a jet ski ride in the tropics?

When we weren’t taking part in Key West’s three favored pastimes, we filled our hours by riding bikes around the entire island, watching the buskers at Mallory Square (where there’s a nightly sunset viewing party), and going parasailing. We played like 12-year olds for about an hour on one of those trampolines in the middle of the water. I’m sure we looked strange — giddy 30-somethings, laughing like maniacs — but no one seemed to care.

“Down here, you could walk with your underwear on your head and no one would be bothered,” Paul Menta told me later. “You’d just get a nickname then be accepted like everybody else. Our differences just aren’t a big deal. It’s pretty cool, man.”

Almost everyone I chatted with about the island echoed Menta’s idea of acceptance. It’s something of a local buzzword. Between, Fantasy Fest in late October, the popular Pride event in June, and the beloved drag shows, Key West feels progressive in a way that much of the south doesn’t. Perhaps this is a vision for a new American utopia: with so many people drinking, riding on jet skis, and watching sunsets, who has time to be a jerk?

Leaving Key West, we couldn’t help feeling like the island’s residents had a few things figured out. Way back in 1982, they staked their claim to independence and now, nearly 35 years on, in one of the weirdest political years ever, they embody so many of the things that we could use more of on the mainland.



Where to stay: The Gates Hotel. The pool/food truck/free bike rental combo is unbeatable. Plus the sheets and pillows are really, really nice.

Where to eat: The Stoned Crab. Get the Gulf Stone Crab claws — probably the best single dish I had in 2016.

Where to drink: Captain Tony’s Saloon. This place pretty much nails the Tropical Island-Americana hybrid that is Key West.

What not to miss: The Hemingway Home is worth the visit. It’s not an afternoon, it’s an hour, and getting to see a little slice of Papa’s life in an hour is a treat.