Cortadito Conch Chickens
A Star RM guide to Key West, Florida, USA
”A great and corrupt gardenia of an island.”
- Tom McGuane
There’s something wonderful and unsettling about being the last stop on the continent. For those looking to get away from it all, Florida’s Key West is the end of the line.
This remote speck was first settled by the Indigenous Calusa people, followed by the Spanish Explorers who passed through in the 1500s, then the pirates had their day in the 1700s, then the US claimed the land for various strategic military purposes in 1800s, then things skewed more commercial in the 1900s to the point where today the island is mostly dedicated to various leisure pursuits such as eating cheeseburgers in paradise.
The last habitable island at the southernmost point of the continental US barely pokes above the vibrant waters between the Gulf of Mexico and the Straits of Florida that rush out into the Atlantic Ocean. You can fly, ferry or drive yourself here along the scenic, harrowing, 113 mile long, Overseas Highway.
Well, it’s scenic if you traverse it during the day. For Jen and I, our flights were cancelled and we ended up doing the entire four hour drive from Miami to the island between 9pm and 1am. Fortunately, many more stretches than I imagined are on land, but the 42 bridges, most of which are poorly lit, two lane highways, require the utmost concentration after dark. Roads stretch into the abyss, the inexplicable miniature Key Deer are plentiful, and I found myself almost hallucinating for numerous stretches where you can’t tell if the lights in the distance are cars, ambulances, or UFOs.
However you arrive, you’ll eventually gravitate to Key West’s Old Town which still retains—barely—a particular seductive atmosphere rarely found in America. The air is salty. The homes are tiny. The foliage is unruly and lush. Many bars, cafes, and restaurants exist in jungle settings. Hot, sweet, cortaditos can be found at sidewalk stands. Businesses are quirky, independent and diverse with no chains in sight. No Starbucks. No high-rises. No parking lots. No gated communities. Most everything is within walking distance, and it’s the perfect place to rent a scooter. You’re more likely to see a Cuban flag or the Key West Conch Republic flag than the American flag. Geckos and chickens—yes, chickens—roam freely with people from all walks of life in the streets. Italian tourists. An Indian family on detour from their Disney vacation. A group of gay friends on holiday from the UK. Afro-Caribbeans. Honeymooners. Acid trippers. MAGA types. Hippies. Yogis. Runaway teens. Midwesterners on a never-ending bender. Mostly-naked cyclists. The occasional linen-suited dapper gent.
Beyond your local island mates, half the fun of being in Key West is exploring the back stories of the wide array of history-makers, pioneers, artists, addicts, bohemians, recluses, sportsmen and world class bamboozlers that have strutted down its sun soaked lanes. From Hemingway to Judy Blume, Edison to Truman, with some Shel Silverstein thrown in for good measure, there’s lots to read up on and explore.
Bar hopping and Hemingway house-hunting are worthwhile, but getting yourself on a boat is a must. There are package deal day trips of every persuasion—the kind of thing where you cruise off shore to watch the sunset with a complimentary cocktail—but the way to go is to charter a boat and choose your own adventure. Flat fishing, deep-sea fishing, reef snorkeling, sandbar swimming, mangrove touring, sea-kayaking, deserted island hopping, or pick a tranquil spot to drop anchor and have a transcendent happy hour.
If you do hire a boat, most can take you just about anywhere, weather-permitting, so do some research on your activity of choice before hand and have a couple options in mind. On our recent visit, we were winging it and didn’t have a clear plan because there seemed to be so many options. I’m not a fisherman, but I wanted to try fishing the flats. But I also wanted to find a remote idyll to swim and snorkel. And I also didn’t mind the idea of just cruising along while sitting on the boat deck and admiring cloud formations with a bottomless cooler of cold beers nearby.
All this added up to an itinerary that didn’t stray too far from shore, but led us to a desolate sand bar where the captain popped a couple kayaks in the 80 degree water, tossed overboard a soft cooler stashed with beers, ice, tequila, limes, soda and sandwiches, and let us drift off on our merry way across the lapping sea to cobble together our own waist deep four cocktail lunch. Still feels like a dream.
Go-getters will figure out a way to sail to the Marquesas Keys or Dry Tortugas for their hardly touched waters. And for the truly industrious, it is indeed possible to do a day trip to Cuba via private airplane or boat charter. These itineraries were advertised in numerous local publications and casually suggested by multiple bartenders who “knew a friend with a boat.” Timing was such that we couldn’t see this particular escapade through, but what an adventure that would be!
If you do stay on land, I found the notion that “Key West has no beaches” to be a myth. Fort Zachary Taylor Beach was easy to access and was a great place to catch a sunset. If you bring a hammock, you can string it up to the non-native pine trees that were imported from Australia to create a uniquely shaded beach environment.
For reasons that I still don’t fully understand, it is nearly impossible to find good seafood on Key West. You would think the island’s proximity to one of the world’s premiere fishing channels would grant it access to some fresh quality fish. Not the case. Oysters were awful. Don’t bother with the conch. Filets were smothered in thick sauce. Closest thing I found to good seafood was the fried hogfish sandwich from Hogfish Bar and Atlas Izakaya crafted some nice bites. But if you remind yourself that you are really here for the tropical heat, the debaucherous dives, the immaculate flats, and the cotton candy sunsets, then you’ll be happy.
Here’s my guide to some highlights…
Blue Heaven - Key lime pie under a banyan tree
Atlas Izakaya - King crab tacos
Lola’s Bistro - Veal medallions
Cafe Sole - Hogfish Snapper Sole
Cafe Marquesa - Hot and cold foie gras
Chart Room, Cold beer and hidden gem vibes
Captain Tony’s - Cold beer and Hemingway vibes
Green Parrot - Cold beer and live music
Don’s Place - Cold beer and local drunks vibes
Hogfish Bar & Grill - Cold beer and a Hogfish sandwich
Boat Charter - Sandbar picnic
Cuba Daytrip - Havana in-and-out
Bocce Courts - pick up bocce match by the sea
Kimpton Winslow’s Bungalow’s - Midnight swim
Besame Mucho - Thoughtful gifts
Hemingway House - Second floor bathroom tile
Fausto’s Fleming Street - Beach picnic supplies
Sandy’s Cafe - Sidewalk cortadito
Fort Zachary Taylor Beach - Sunset through the pine trees
Books & Books - Local author browsing
Local Legends
Many a memorable character has graced this tiny island. To name a few…
Judy Blume - Even at 86 years old, you can find the famous novelist, and long time Key West resident, managing her book store that is part of a dynamic, multi-use space she co-founded which includes a performance auditorium, artist studios, and a gallery.
Vince Vaughn - The actor filmed the entertaining comedic crime series, Bad Monkey, in Key West in 2022 (the series was recently renewed for a second season and will take place mostly in Los Angeles).
Jimmy Buffet - Legendary singer, songwriter, and entrepreneur who is synonymous with all things Key West. He lived on the island through the 70s and 80s. Many of his most famous songs were written on or about the island. Upon his death in 2023, his net worth was over $1 billion, making him one of the world’s richest musicians.
Shel Silverstein - Amongst his other homes in Sausalito, Greenwich Village, and Martha’s Vineyard, the writer and cartoonist spent the last few decades of his life in Key West, passing away there in 1999.
Tom McGuane - Writer and angler who moved to Key West in 1970 and wrote several books about the island including Panama, Ninety-two in the Shade, and Cloudbursts.
Jim Harrison - One of the “Fat Boys,” a gregarious group of writers, anglers, and all around partiers who spent many winters on the island in a stupor during the 70s.
Tennessee Williams - Southern Gothic playwright, perhaps most famous for his Pulitzer winning play, A Streetcar Named Desire. He lived on the island for over thirty years between 1949 and 1983.
Harry Truman - The nation’s 33rd President spent 11 “working vacations” for a total of 175 days of his presidency between 1946 and 1952 on Key West. His home became known as the “Little White House",” and can still be visited today.
Ernest Hemingway - World renown writer, drinker, hunter, fisherman, journalist, ambulance driver, and lover of of cats who penned numerous novels when he lived on the island between 1931-1939. In 1938, he set a “world record” for catching seven Marlin in a single day off the coast between Key West and Cuba.
Thomas Edison - The genius inventor was stationed in Key West for six months in 1917 during WWI, working on depth charge experiments for the Navy.
Henry Flagler - Industrialist and Founder of Standard Oil. Key figure in the development of much of the southern Atlantic coast including primary investor in the original railroad to Key West that was completed in 1912.
Winslow Homer - The painter visited the island between 1886 and 1904, and he produced numerous works while there including A Norther, Hauling in Anchor, and Taking on Wet Provisions.
All That is Sacred - A wonderful documentary produced by Yeti, which is largely based off an obscure 1974 documentary called “Tarpon,” offers a glimpse of the alluring and haphazard 1970s Key West.
Dry Tortugas National Park - If you’re up for a remote adventure and pristine waters, seek out this National Park.
Key West Mooring Buoy System - Who knew you could park a boat for free in Key West?
Civil War-era Key West tidbit - Despite Florida seceding to the Confederacy in 1861, due to the presence of the US Military, Key West never fell out of Union control during the Civil War.
Key Deer - On the islands stretching out to Key West, it is not unusual to encounter the smallest of all white-tailed deer, the Key Deer, which stand only about 30 inches tall. These pixie-like creatures can actually swim from island to island!
Fisherman’s Paradise - The merging of the Gulf of Mexico and the Atlantic Ocean, along with the extensive nearby reef system and warm shallows waters, all contribute to making this one of the best places in the world to fish.
Key West Day Trip - Circumstances change frequently, but apparently, at the moment, thanks to the Office of Foreign Assets Control’s “Support for the Cuban People” policy, you can indeed take a perfectly legal day trip to Cuba from Key West.
The largest underwater treasure find of all time was discovered west of Key West in 1985. Three Spanish treasure galleons sank during a hurricane in 1622 and 500 lives were lost. Over 350 years later, Treasure hunter, Mel Fisher, discovered $400 million worth of gold, silver and rare artifacts being transported by the Nuestra Senora de Atocha. And for a brief period in the 1830s when salvaging shipwrecks was an everyday pursuit for many people, Key West became the richest city per capita in the US.
Key West Little Conch Baseball League - Each island in the chain has their own Little League Team!
You Can Do Magic - I don’t believe this song has anything to do with Key West, other than perhaps it qualifies as “Yacht Rock,”but the video is a must-see for its pastel-clad musicians grooving in an otherworldy cloudscape.
A Key West Playlist
Yacht rock, stoner soul, jazz pop, coastal country, sailor folk.
Jimmy, Steely, Crosby, Lightfoot, etc.
Here you go…
