Where To Eat & Stay In Key West guide image

photo credit: Iris Moore

KWGuide

Where To Eat & Stay In Key West

For when you're in need of Cuban sandwiches, lobster rolls, and key lime pie on a stick.

If South Florida is where folks go to escape from the struggles of adult life, then Key West is where you go to escape from the very concept of reality itself. They do things differently in the southernmost city in the United States. Life down here operates at a leisurely pace, nothing is too formal for sandals, and sunsets are applauded daily at Mallory Square. Food is a huge part of the Key West personality, too. 

This is the land of fresh seafood pulled straight off a boat and enough key lime pie to feed a stadium full of manatees. This guide has our favorite picks for the usual Keys food suspects: conch fritters, grouper sandwiches, and the one key lime pie to rule them all. But it’s also got phenomenal Trinidadian restaurants, Jamaican spots, and more places that are well worth straying from Duval Street, Key West’s own version of Bourbon Street and the island’s tourist headquarters. And since no Key West trip is complete without nightlife, we have a few suggestions on where to go out for live music and the island’s best drag show. Plus, where to stay while you digest it all.


THE ONE NON-NEGOTIABLE KEY LIME PIE


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Kermit's Key West Key Lime Shoppe

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200 Elizabeth St, Key West
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Welcome to Key West, where every man, woman, child, and rooster claims to make the best or most unique version of key lime pie. This is a good problem to have, but they can’t all be telling the truth. So if you’re going to prioritize just one key lime pie spot, make it the one from Kermit’s. This place is a Key West classic that makes a very delicious (and unique) chocolate-dipped version on a popsicle stick. It’s a manageable size, easy to eat while walking around, and overall a pitch-perfect slice of key lime pie. There’s some cute garden seating in the back too in case you don’t want to eat this on the run.


QUICK AND CASUAL


If you’re getting a little tired of the usual seafood, Italian, and Cuban options that dominate Key West, go to Pepper Pot. The small Trinidadian restaurant on a quiet residential street is serving some of the best food in town. They make buttery, warm roti with curry chicken, curry goat, curry shrimp, vegetables, and more. They also serve a really delicious geera pork sandwich that comes on a soft roll with tender cubes of meat and diced Florida avocado. It’s perfect for a little beach picnic or inhaling alone inside the quiet dining room, which is a great place to hide from the loud bars a few blocks away on Duval.


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Our favorite kind of Key West restaurant is an open-air spot mostly made of wood that smells like fried fish. BO's Fish Wagon is the best example of this genre. The little shack serves our favorite seafood sandwiches on the island— cracked conch, fried shrimp, grouper, and more options that all come on soft Cuban bread. One of those and the excellent conch fritters are exactly what you should prioritize here. We like this place for lunch since it's quick and casual, but it's also worth stopping by for some beers, snacks, and live music on Friday night.


The Conch Shack is, like the name implies, a great place to get one of Key West’s greatest dishes: conch fritters. They’re big, not too greasy, and come with a wonderful key lime aioli for dipping. But this small, cash-only sidewalk stand also serves one of the better Maine lobster rolls on the island, with a generous amount of meat. Other options include fried shrimp, a fried mahi sandwich, burgers, hot dogs, and more food you’ll want after several drinks, which is when a lot of folks end up here thanks to its Duval Street location. The Conch Shack is open until midnight on the weekend too, so keep this place in mind after bar hopping.


You’ll pass this place on your way in and out of Key West, and it’s worth a stop if you want a styrofoam box full of outrageously good Jamaican food. The takeout operation has bounced around in the last few years, but is currently operating from a strip mall on North Roosevelt Boulevard. They have classics like an excellent jerk chicken with a perfect smoky heat, but also some unique options like their own version of a Cuban sandwich (called a “Jamaicano”) with tender jerk pork, swiss cheese, and pickled peppers. It sort of feels like the sandwich equivalent of hearing a great cover of your favorite song. Because Yahman’s is such a small operation, check their Instagram before you visit for the latest info on hours and location.


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If you told us we had exactly one hour to eat as much of the best local seafood in Key West, we’d just go to Eaton Street for an hour and order the entire menu. This little seafood market has an impressive selection of local options: hogfish, shrimp, fish dip, lobster, stone crab, conch, grouper, and what feels like a thousand other choices. You can take any of it home to cook yourself, but (no offense) they’ll do a much better job. All that fresh stuff gets turned into an excellent lobster roll, fried or grilled fish sandwiches, beautiful little fried shrimp, grilled lobster tails, and more. You can eat it all on their shaded patio with a beer, and since the restaurant isn’t in a particularly crowded area, it’s a great option for a somewhat quiet lunch or dinner.


The Cuban sandwich—and Cuban food in general—is a huge part of the Key West food identity, and our favorite comes from Sandy’s. The little sidewalk ventanita (a Cuban term for a little takeout window) attached to a laundromat has been around since the ‘80s, and the family that owns it has been making Cuban food in Key West for much longer. Sandy's does things with the Cuban sandwich that would get you some strange looks in Miami, like adding salami, lettuce, tomatoes, pickles, and mayonnaise, but it all works great together—and you can always just stick to the basics. Sandy's is located a bit north of most of the hotel and tourist action, so if you're looking for a closer (and more classic) Cuban sandwich option, go to Ana's Cuban Cafe.


PERFECT FOR BREAKFAST


La Grignote is where you want to go for a sit-down brunch involving some combination of bread and eggs. The cute French bakery has indoor and outdoor seating, alcohol options, and a big menu with benedicts, a Croque monsieur, and an excellent crispy-on-the-outside, tender-inside Belgian waffle. You’ll probably encounter a wait, especially on the weekends, but you can also order some stuff to go from their pastry case if you’re in a rush. It has bunch of things that are easy to eat while walking around, like a circular disk of key lime pie, a deluxe version of pigs in a blanket, and great croissants.


Whether you were already hunting for a donut, or this sentence just made you realize how badly you want one, go to Glazed Donuts. The shop is just a block away from Duval, and has over a dozen really tasty options. They, of course, make a very good key lime donut with a tart key lime filling and little globs of meringue on top as well as a very good classic glazed and a Cuban coffee version. The shop isn’t great for big groups, but there are plenty of tables for two. And they’re also home to the local coffee roaster Red Buoy Coffee, so it’s a good place to stop for some caffeine.


NICER DINNER SPOTS


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A&B Lobster House

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So many of the nicer sit-down dinner spots in Key West have menus that feel just a tad outdated, with resort food we don’t necessarily find exciting. But at A&B Lobster House, the history is kind of the point. This waterfront spot has been around for over 70 years, and is still one of the best upscale dinner options—with one caveat. You’ve got to sit outside. The waterfront view from the patio seating really makes the experience of sipping $17 martinis and cracking $50-plus lobster worth it. So make a reservation, and make it early. You might have a tough time getting a table during busy season, although their bar is walk-in friendly and has a lounge area with a nice waterfront view.


If you’ve done even a tiny amount of research on where to eat in Key West, you’ve probably seen the words Blue Heaven. This classic spot is one of the most recommended restaurants in Key West, and we agree that it’s worth a visit. That’s not because of the seafood-heavy menu though—which is fine, if a little antiquated—but because there’s just something about the outdoor space that channels the very essence of Key West. Blue Heaven is a Jimmy Buffett song come to life: tables are scattered beneath a huge tree that hangs over the entire restaurant and there’s usually live music playing at the ideal volume. If nothing on the menu is speaking to you, just get the very good cheeseburger, a slice of their famous key lime pie with a ridiculously tall hat of meringue, and order something with rum in it. There will absolutely be a wait during busy season, so it’s worth it to call a few weeks ahead and make a reservation.  


WHERE TO GO OUT IN KEY WEST


If there is one bar that represents everything great about going out in Key West, it’s Green Parrot. This place has all the Keys nightlife staples: excellent nightly live music, a wooden interior that’ll make you feel a little like a pirate, and bar seating that makes it easy to befriend strangers. It's a well-deserved classic, and is just as fun at 2pm as it is at 2am. The building has been standing since the late 1800s and if you’d like to know what the scene looks like before you go, they have a live webcam streaming all day, every day.


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Key West bars, especially the popular ones, can get crowded. So if you’re looking for somewhere to escape—and if you generally prefer drinking at a dive bar—go seek shelter at Chart Room. This Key West staple is impossible to stumble upon unless you know about it, as it’s located inside a bougie resort, but completely open to the public. Every inch of the small room is covered in a flag, photo, or bumper sticker, and it’s quiet enough for a conversation or a game of backgammon over a very tasty Old Fashioned. Also, there are complimentary peanuts and hot dogs for anyone brave enough to reach into the slow cooker.


LGBTQ culture is foundational to Key West—especially its nightlife. That’s why drag is big on the island, and the best (and rowdiest) place to partake is at 801 Bourbon Bar, a gloriously pink building that hosts the most fun drag show in Key West. The ticketed show happens upstairs, on a small stage in a cramped room. It’s a hilarious evening where you might very well become part of the performance if you’re sitting close enough to the stage. The show is 18 and older Monday through Thursday, and 21 and up Friday through Sunday for reasons that will become obvious approximately five seconds into the show. 


THE HOTELS


If staying in a hotel on the beach isn’t terribly important to you—and you are fine with the concept of benevolent ghosts—then consider The Artist House. The historic property was built in the late 1800s and has since been been converted into a bed and breakfast, so expect medium water pressure and slightly creaky floors. But this place has everything we love about Key West: friendly service, a great little backyard with a small pool, and a complimentary daily Happy Hour. It’s also no more than a 15-minute walk from pretty much everything you could want to do in town. The building used to be home to the most famous haunted doll in Key West, Robert The Doll. Google the little dude if you must, but we can confidently say that the only spooky thing that happened during our stay here was the realization that we forgot the beer at home.


If staying in a hotel on the beach is terribly important to you, check out Pier House. This big hotel is located on Duval, but at the very north end, which is a safe distance from the boozy chaos of the touristy street. This place has its own small and very secluded beach that only guests can access. The property also houses one of the greatest dive bars in all of Key West, Chart Room. The bar is an excellent spot to end every night of your trip with an Old Fashioned and free peanuts in a room where Jimmy Buffett allegedly used to strum away.


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