Overall grade: B-

In a word: Definitely not a must-see, Key West still makes for a pleasant-enough getaway if you happen to be in that part of the world.

More words: I recently spent a few days exploring the Florida Keys. It’s a beautiful part of the world, though not exactly what I expected. For starters, getting to the keys involves driving for several hours on a series of bridges between the various islands of the archipelago. It’s a beautiful drive, but the typical travel photos of the journey might oversell it a bit; there are long stretches where the view is obstructed by vegetation, concrete barriers, buildings, etc. If I had to do it again, I’d fly into Key West or Miami and just venture out from there.

If you do end up driving the Keys, I recommend getting out and walking on the pedestrianized Seven Mile Bridge, which offers an experience closer to the one I expected after having looking at photos of the keys.


Key West itself struck me as a place trying to capture the late middle aged escapist crowd. That makes sense — it’s a lucrative group — but it’s not really my scene. More than anything else, Duval Street and the surrounding environs struck me as being like Bourbon Street in New Orleans, but in the places where the action starts to peter out.

Key West also seemed to swing between very touristy sites and nothing at all; things like the Hemingway Home and the Southernmost Point swarmed with visitors, but after walking a few blocks it felt like a pretty ordinary neighborhood. Cities like New Orleans or Boston or even Portland (not to mention Paris or Venice) are a pleasure for visitors to simply stroll and explore. Key West was less so. Exploring isn’t unpleasant and it struck me as a great place to be a local, but for a tourist there aren’t a lot of architectural wonders, good art, markets, etc.

IMG_0051Key West also struck me as a weird mix of a quirky remote town — the kind of place where people have a bizarre (often charming) mix of old junk on their porches — and a gentrifying resort town.

Not worth it: The Hemingway Home. Do you think Ernest Hemingway — a man who went on safaris, was wounded by a mortar, and galavanted all over the world — would approve of standing in a long line to see a for-profit tourist attraction? No, no he wouldn’t. If you really like Hemingway, read one of his books. This trap is not what he would have wanted.

Where to eat: El Siboney. This casual Cuban restaurant serves absolutely delicious food. It’s affordable and has a family atmosphere. The fried bananas and boiled yucca were some of the best I’ve had anywhere ever. This restaurant is very unassuming, but it may be worth visiting Key West just to eat here.

Dessert: Kermit’s Key West Key Lime Shoppe. This place gets a lot of hype (as I discovered while researching key lime pie on the drive down) and lives up to it. There are two locations and I tried the one on Duval Street.

Further reading: Last week The New York Times explored Key West’s Cuban coffee culture.


Written by Jim Dalrymple II

Urbanism and travel writer. Also a journalist covering the news.


  1. Ate at that same pie shop when we were there a couple years back. We also stayed right next to 7-mile bridge, and every morning would walk it and see giant manta rays, sea turtles, eels, fish, iguana, and so on. The people and city are kinda unique/quirky/whatever, but I really enjoyed the nature of the keys—that’s what makes it worth the visit back.

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