key west

Could I Live Here? Key West Edition

Key West is a unique little slice of paradise. There’s plenty of culture, great food, sun, and a laid back attitude that is so perfect that it could be fictional. But would living there be heaven on earth or too much of a good thing?


Key West is a little bit of a paradox. Unlike the rest of South Florida, it’s populated by white Jimmy Buffet types who drink Miller Lite and would rather be fishing. But it’s also one of the most progressive cities in Florida outside of South Beach. It’s where Salt Life meets gay pride, and everyone magically gets along. The humble houses from another time give you the kind of wholesome feeling you get walking through Main Street in Disney.

key west

By contrast, Key West is full of brightly painted shops and bars – a sign of its youthful spirit. It’s quaint without being boring. Because let’s face it, these folks know how to party. Duval Street is a shitshow any night of the week, but it’s not pretentious or exhausting. You can bar-hop in flip flips and get a well drink for $3. And I can totally imagine making a life for myself playing acoustic covers of Stones’ songs at Willie T’s or selling paintings on Mallory Square (Yeah, I have other talents). In Key West, anything seems possible.

key west mallory square


The food in Key West, second only to the food in New Orleans, is the best in the country. Sorry, NYC and San Francisco. Your gourmet burgers and fancy sushi rolls can’t hold a candle to a paper plate of shrimp tacos at DJ’s Clam Shack. I think what makes it so appealing is that you can have a fantastic meal anywhere you go without dealing with the pretentious overtures of a really nice restaurant. You’re often sitting on mismatched chairs outside surrounded by chickens, and eating the best meal of your life. If you’re in the mood to be fancy, you can dress up (though you still won’t look better than the drag queens on Duval). But by the same token, no one will care if you’re still in a soaked bikini at dinnertime. And even though I’m a chocolate person, there’s no better dessert than a big slice of key lime pie. Except the slices that are dipped in chocolate.

key lime pie key west

The only real downside of the island’s amazing food is how fat and sick I would probably get if I lived there full time. I would just be chowing down on fire roasted corn and having lavish desserts at Better Than Sex every day. I can definitely see me becoming insulin-dependent after like a month. But if I’m ever on death row, one of the only suitable last meals would be the lobster eggs benedict from Blue Heaven.

blue heaven key west


Everyone who lives in Key West is awesome because they’re really happy. So even in the 5 minutes you’re ordering a drink or browsing someone’s craft table, they’ll take a genuine interest in you and how you ended up on their amazing little key. And it’s nice to be treated with such kindness and surrounded by people that are so friendly.

The downside of the people there is that they’re 60% tourists. I would definitely have to adjust to the crowds that always seem to be in your way and walking slower than you. Or maybe I just need to learn to drop my hurried big city gait. Of course, the city is also full of retirees. This is both good and bad, because it’s nice to see people enjoying their life. But it can also be kind of depressing. Because the person alone at the bar on a Tuesday at 11 am could have an alcohol problem. The old lady with a wistful smile and her eyes closed listening to Mrs. Robinson could be reliving better years of her life. And I guess I have to ask myself, do I want to be that lady?

key west people

Actually, yeah, I would definitely want to be her. She looked like she was having a great time.


The cost is one of the only downsides of Key West. A one-bedroom apartment can be upwards of $1,500-1,600, and if you’re looking for anything a little more spacious, you won’t find a place for less than two grand. That’s definitely kind of a bummer and makes it just a little more stressful than the guy selling hand-rolled cigars on the street might have you believe it is. On the other hand, unless you’re eating lobster every day, food and drink can be very affordable. And it’s an island, so the only form of transportation you need are your legs. So there’s certainly a tradeoff there. I suppose if I owned a comfortable boat, it would be much more affordable to live there.

key west


But an even bigger downside is the weather. Like all of South Florida, rain showers are torrential and random. And when it’s not raining, the sun is hot enough to sear any exposed skin. Given that being in the Keys involves so much walking and being outside, the humidity and heat can be intolerable. I don’t know that I would enjoy living in a place where I sweat 3 gallons a day all year. I like winter and fall, and wearing things other than shorts and bikinis. Plus, I don’t want to commit to having leathery skin golden enough to make a nice purse.

key west

And aside from the year-round weather, there is the threat of the occasional tropical storm or hurricane. I’m not particularly attached to many material possessions but I also don’t want to live somewhere where I might lose them all in a couple of hours. The idea of having to evacuate with thousands of other people on a one-lane highway also kills my vibe. Even driving back from the Keys on a Sunday is terrible. I can’t imagine what that place is like when a Category 4 is on its way. That’s a kind of stress I don’t really want in my life.

Total Livability Score 6.5/10

I do love Key West. I think it’s one of the most magical places on Earth. But the downsides of living there prevent me from being more enthused about the idea of becoming a semi-permanent resident. But I certainly wouldn’t be opposed to a short stint during the winter.

key west florida


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