There’s a moment on the Overseas Highway — somewhere after you’ve passed the last strip mall in Key Largo, just as the land thins into water and the radio crackles with Jimmy Buffett — when you feel it: Key West isn’t a destination. It’s a detour from reality.
End of the road? Sure. But also the start of something freer, saltier, stranger, and unmistakably Sunshine Republic.
What it is
Key West is Florida boiled down to its wildest, most romantic self. Part Caribbean outpost, part Hemingway novella, part Technicolor fever dream. It’s the southernmost point in the continental United States, closer to Havana than to Miami, and it feels like it.
Roosters strut like they own the place. Conch cottages bloom with bougainvillea. The air smells like salt and rum and stories. Key West doesn’t just welcome eccentrics — it elevates them to local royalty.
How to Feel It, Not Just See It
Skip the cruise crowd checklist. Yes, see the Southernmost Point marker, but don’t linger. The real Key West lives in alleyways and porches, in bars that don’t close and conversations that meander like tide.
Spend your day walking. No Uber needed.
Start Here: The Historic Seaport District
The smell of boat fuel and fresh shrimp. Sailboats bobbing. Fishermen swearing gently. Walk the waterfront boardwalk past the Schooner Wharf Bar and Turtle Kraals. Watch the sun rise here, not just set — fewer tourists, more magic.
The Best Things To Do (And a Few to Skip)
1. Ernest Hemingway Home and Museum
The man, the myth, the six-toed cats. Hemingway lived here during his most prolific years. The home is frozen in time — typewriter, Spanish tile, pool, and all. Hemingway Home
2. Fort Zachary Taylor Historic State Park
Where you go when you actually want a beach in Key West. Turquoise water, shady pines, and Civil War-era cannons thrown in for good measure. Fort Zachary Taylor
3. The Green Parrot
Not just a bar — an institution. Come for the music, the free popcorn, and the stories. Local tip: sit in the back and listen before you order.
4. The Studios of Key West
Part gallery, part performance venue, part artist refuge. Key West is a town of creators, and this is where they gather. The Studios
5. The Cemetery
Yes, the cemetery. Famous for its quirky headstones (“I told you I was sick”) and shaded walking paths, it’s a microcosm of the island’s irreverent soul.
Skip: The overly commercial Mallory Square at high noon. Go at sunset instead, but only for the buskers — the cat guy, the fire jugglers, the acrobats balancing atop shopping carts. It’s Key West vaudeville.
Local Flavor (Literally)
Eat:
- Blue Heaven – Chickens roam the courtyard. Banana pancakes come stacked high. Gospel brunch is real. Blue Heaven
- Garbo’s Grill – Korean BBQ tacos out of a silver Airstream. Perfection.
- El Siboney – Cuban food like your abuela dreams about. Order the roast pork and a café con leche. El Siboney
Drink:
- The Rum Bar at Speakeasy Inn – Best rum selection on the island. Ask for the rum flight and a story.
- Captain Tony’s Saloon – The original Sloppy Joe’s and a dive bar of legendary status. Hemingway drank here. Jimmy Buffett played here. You should too.
Where to Stay
Key West is small but rich with vibe. Choose wisely.
- The Marquesa Hotel – Quiet luxury in Old Town with a garden pool. Booking link
- Heron House – Adult-only, intimate, and shaded with orchids. Booking link
- El Patio Motel – Vintage Art Deco vibes for those on a tighter budget who still want charm. Booking link
Why It Matters
Key West isn’t like the rest of Florida — or the rest of America. It’s a city that has embraced misfits, exiles, wanderers, poets, and drunks and somehow turned all that into civic pride. It’s where Tennessee Williams wrote plays, where Judy Blume writes books, where wreckers became millionaires, and where roosters outrank cops.
The Conch Republic declared independence from the U.S. — and then held a surrender ceremony the next day. It was satire. It was protest. It was art. That’s Key West.
To come here is to be reminded that weird is a form of wisdom, and that beauty lives in the cracks. The Sunshine Republic salutes the Conch Republic.
Here’s What I’d Do:
Arrive by ferry or take the slow drive down the Overseas Highway. Walk the island. Eat too many shrimp. Talk to a bartender who’s lived here 30 years. Sit in the shade and read something written here. Then watch the sun fall into the Gulf like it’s the last time the world will spin.
I once found a paperback copy of A Moveable Feast on a bar stool at Captain Tony’s. I read three pages. The bartender gave me a beer on the house. The jukebox played Warren Zevon. That was Key West, too.
