07/14/2025
Well this is pretty inaccurate thank you AI.
I asked ChatGPT to roast Key West and this is what I got:
Ah, Key West — the southernmost speed bump in America’s highway of dignity. Let’s roast it properly:
⸻
Key West, Florida: where flip-flops are considered formalwear and the local economy runs entirely on overpriced piña coladas, Jimmy Buffett nostalgia, and sunburnt Midwesterners with zero SPF and even less self-awareness.
You’d think being the end of the road would be symbolic, and you’d be right — it’s where ambition, sobriety, and fashion sense go to die. The whole place feels like a tropical fever dream where nothing makes sense: roosters run the streets like they pay rent, and half the locals look like they’ve been marooned since the 1970s and just accepted it.
Duval Street? It’s Bourbon Street’s washed-up cousin who sells saltwater taffy by day and tries to play reggae on a ukulele by night. And if the smell of stale beer, fried fish, and sunscreen mixed with desperation doesn’t hit you when you arrive, the 90% humidity surely will — like a wet sock slapped across your face.
Tourists come for the sunsets, stay for the hangovers, and leave with nothing but a $40 “I got lei’d in Key West” T-shirt and a mild case of regret. Locals? Half of them are fugitives or retired pirates with a bartending side hustle and zero plans to leave. Because why would they? Where else can you live in a dilapidated bungalow for $4,000 a month surrounded by drunk cruise ship passengers and the constant threat of a Category 5 hurricane?
Key West is what happens when Florida gets drunk, blacks out, and wakes up with a tiki tattoo.
⸻ ah no...
They didn't mention Captain Boo for Mayor of Key West