With all the lovey-dovey things I say on my blog about Key West, from the delicious restaurants to the idyllic sandbars, you might be wondering what’s being left out. Are there any bad things about Key West?
Well, for all the pessimists out there, here’s a look at the not-so-great things about this little rock. But don’t worry, there are still lots of great reasons to visit Key West, too!
9 Bad Things About Key West
Life on the island can’t be all good. There are plenty of bad things about Key West that you might not realize. For some reason, all the tourist brochures leave these things out!
Here’s my round-up of the nine worst things about Key West.
Key West Parking Is Simply Awful
Key West is a little postage stamp of an island, and the streets of Old Town were laid out way before people were driving their Excursions and Tahoes everywhere. Heck, the town was here before you could even drive to the island! There just isn’t enough parking for the people who live here, let alone for all of America to drive down and find a spot near Duval. So the parking can be, in a word, a nightmare!
There are only two tricks to finding parking in Key West: Learn where to park for free or rent a bike. If you’re staying in a hotel that isn’t within walking distance of town, see if they offer a shuttle or call a ride share. Anything to avoid the chore of trying to find parking in Old Town on a busy evening!
Key West Drinks Are Expensive
Good news, bad news time. Bad news: Key West has its share of overpriced drinks, like every touristy beach town. Maybe it feels more acute in Key West since the drinks are so yummy here.
The good news? Happy Hour in Key West! That blissful time of day when drinks get cheaper, taste better, and make you sound smarter. Well, they’re cheaper, at least.
You Will Gain at Least Ten Pounds in Key West
Key West is not good for your waistline. The island is jam-packed with fantastic seafood, local specialties, and superb restaurants. From takeouts to fancy fine dining, you can find a little of everything in Key West. And with such stiff competition, many places will surprise you with the level of food you get. Be sure to check out my guide to Key West’s best restaurants, but honestly, there are many to choose from to suit every palette and budget.
Your Dentist is Getting a Yacht
Speaking of tasty treats, Key West whispers sweet nothings to you after every meal, too. Key Lime Pie, juicy cocktails, candies, ice cream, and all sorts of crazy confections.
You might notice that the dentists here all wear boat shoes, and they’re only open two days a week. They spend the rest of their time on their yachts, which they bought with the money they made from filling all our cavities.
Cockadoodle-Flippin-Do
The island is overrun with Key West chickens, if you didn’t know. They wander the streets with impunity, clucking and ca-cawing all day long. They’re a local mascot; Key West is a place where our spirit animals pop up when you least expect them.
With this in mind, you might wonder why the chicken crossed the road. It was undoubtedly so that it could get under your hotel room window, staged for the 4:30 am wake-up call you requested.
The Key West Hangovers
You might be familiar with it if you started with brunch, slept in the sun until happy hour, and then bar-crawled Duval into the wee hours. There is no hangover like a Key West hangover.
Need to rehydrate? Schedule an IV drip right in your hotel room, a Keys’ specialty.
The Sunburn
Fun fact: If you get out a globe and follow Key West’s line of latitude, what part of Europe do you think is the same distance from the equator? Ha, it’s a trick question! Key West is equal to Northern Africa, lying at the same latitude as the Sahara Desert!
What’s the point? The sun is more intense here than anywhere else in the US (except in Hawaii). There’s a big landmark somewhere around here that says as much. But all that sun will irradiate your skin like there’s no tomorrow. So put on good sunblock every day because the dermatologists around here wear boat shoes, too.
The Key West Hangovers
You might be familiar with it if you started with brunch, slept in the sun until happy hour, and then bar-crawled Duval into the wee hours. There is no hangover like a Key West hangover.
Need to rehydrate? Schedule an IV drip right in your hotel room, a Keys’ specialty.
Fancy Clothes Rot Away
If you packed your bag full of tuxedoes, dinner jackets, or cocktail dresses, it’s probably rotting away. This island demands flip-flops and t-shirts — nothing more, but maybe less. You won’t wear any of those expensive clothes that you brought; Key West just isn’t that sort of place.
That doesn’t mean that Key West is trashy or unsophisticated. It’s just that the island has a way of making you realize what’s important and what’s not. Being in Key West is important, and dressing like you’re boarding the Titanic is not.
Key West Ruins All Other Vacations
Key West is a special place, and there’s no way around the fact that every other vacation you could take pales in comparison. Who else has this combination of beautiful water, beautiful coral reefs, stunning sandbars and beaches, and a walkable, historic Old Town to explore?
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- The rest of Florida? Too crowded!
- California? Solid meh!
- Cancun? Please!
- Europe? Too far!
- Anywhere else? Not Key West!
Key West has just the right mix of things that leaves you wanting to come back year after year.











