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17 Food And Drinks You Have To Try In Key West – Tasting Table

If you’re looking for a winter getaway, you can’t go wrong with Key West. The island is located at the very tip of the Flordia Keys, connected to the other islands by the Overseas Highway, and you’ll reach mile zero on the U.S. 1 Highway when you drive to the end. Its tropical-maritime climate means summer and winter temperatures rarely vary more than 10 degrees. That means Key West maintains 75 to 80-degree days in the winter, making it a welcome paradise for those who live in frigid, snowy climates.
After spending a week in Key West, we found all the best places to eat and drink while on vacation. Narrowing it down was way more complicated than we thought! Geographically, Key West is a hub for Cuban food and other Caribbean specialties, but you can’t go wrong if you’re in the market for seafood, either. Depending on the season, you’ll find seafood-heavy menus featuring grouper, snapper, mahi-mahi, stone crab claws, Key West pink shrimp, and spiny lobster. Beyond the food, the island is known as something of a party scene, and you’ll find great music and ice-cold drinks at almost every turn.

The Schooner Warf Bar is part of the historic harbor walk along the Key West Historic Seaport. In the 1940s, ships unloaded their sea turtle catch here (a practice that is no longer legal), and today it’s the best place for a seaside stroll or catching a sunset cruise or a fishing charter (via Florida Rambler).
The open-air Schooner Wharf Bar is located right off the docks. Take a seat at the covered bar or wander through the dozens of tables on the patio, each with a colorful umbrella to shade you from the sun. There’s live music almost every night, and rumor has it that Kenny Chesney is known to frequent the establishment. The Schooner is well-known for margaritas, but we’re here for the frozen Key Lime Colada — a delightful frozen blend of colada mix, lime juice, Blue Chair Bay Key Lime Rum, and Blue Chair Bay Coconut Rum (a company owned by the aforementioned Chesney). If you’re a cigar aficionado, the restaurant also has a cigar stand selling dozens of options.

There’s no shortage of good Cuban food in Key West, which is a short 90 miles away from Cuba. Significant numbers of Cubans began emigrating to the Florida island starting in the early 1800s. The local population provides plenty of sit-down Cuban dining experiences in Key West, but our favorite was the Cuban Mix sandwich at the casual counter-service restaurant Cuban Coffee Queen.
The local chain has three locations where the team also roasts coffee (and make a pretty mean café con leche). The sandwich contains juicy shredded mojo pork, sliced ham, and Swiss cheese pressed on a panini grill until it’s crispy on the outside and melty inside. The tangy pickles, assertive mustard, and creamy mayonnaise played well together to keep the sandwich moist, and the soft Cuban-style bread really brought it all together.

El Siboney Restaurant is a family-friendly sit-down restaurant tucked away on a side street in Key West’s historic Old Town district. It’s far enough from the excitement of Duval Street but convenient enough to walk from almost anywhere on Key West’s west side. Only blocks away from Higg’s Beach, it’s a fantastic lunch spot before or after your morning tanning session.
You can’t go wrong with anything on this menu (a side of yuca frita is worth getting if you’ve never tried the tropical starch). The dish we keep coming back to time after time, though, is the vaca frita — “carne desmenusada ala plancha,” or shredded beef that’s been crisped-up on a hot griddle. The platter is large enough to split, but do yourself a favor and get a second side of beans if you’re splitting. They’re perfectly salty and tender, and you’ll definitely want your own cup.

Key West is a fisherman’s paradise, so it’s no surprise that you can get out there and catch dinner yourself. You could buy a visitor’s fishing license and cast from the bridges or docks, but getting out on a boat is much more fun. A charter also allows you to see some of the finest sights on the open sea.
There are several types of fishing charters, such as offshore trips for tropical fish like mahi-mahi, sailfish, and wahoo or reef fishing for grouper, snapper, and jack. For those who don’t do well in deep waters (hello, sea sickness!), ask your captain for a near-shore fishing experience, like we did with Captain Dan’s Fishing Charter. After four hours, we pulled in seven mangrove snapper and three yellow jack, more than enough to feed ourselves for several days. Turn it into sushi, ceviche, or grilled fish when you get home, or ask your captain which restaurants in town will cook your catch for you — there are several to choose from!

We stayed in a vacation rental with a full kitchen, so we wanted to get fresh seafood to cook at home. When we visited Eaton Street Seafood Market, we realized they also have a full restaurant menu featuring seafood caught from local fishermen.
There were a lot of good-looking items on the menu, including a classic lobster roll, fish tacos, and fried conch strips. If they’re in season, don’t leave here without an order of stone crabs, a regional specialty served with mustard sauce. The dish that captured our hearts, though, was the somewhat plain-sounding blackened fish sandwich. You can choose any fish from the case and have it fried, grilled, or blackened — we opted for the black grouper. The soft ciabatta roll was lightly toasted and slathered with a tangy key lime mustard, the perfect complement to the spicy fish, spring greens, and fresh tomato. It was simple but completely unforgettable.

Sloppy Joe’s is a staple in Key West, and it has an interesting history: Joe Russell, a Key West native who lays claim to having been a charter boat captain for the famous author Ernest Hemingway. Russell leased a building on Greene Street for three dollars a week in 1933, which become the original Sloppy Joe’s. When the landlord raised the rent to four dollars in 1937, Russell recruited a “midnight mob of Key West drinkers” to relocate the bar’s contents to Duval Street.
Today, Sloppy Joe’s is a must-stop on any Duval Street crawl. The drink list is loaded with all kinds of tropical options, but we couldn’t forgive ourselves if we didn’t drink what is said to be Hemingway’s favorite drink in a bar he once frequented. The Papa Doble (“Papa’s favorite!”) is a nod to Ernest Hemingway’s twist on the classic daiquiri. This version features a delightful combination of Bacardi Light rum and grapefruit juice with a splash of grenadine, sour mix, club soda, and fresh-squeezed lime. It goes down dangerously easily, so sip carefully with this one.

Captain Tony’s Saloon is a landmark bar on Greene Street, and it happens to be the original location for Sloppy Joe’s. It is said to be a favorite bar of the late Mike Leech, whose name was carved into a bar stool, while other seats paid homage to legends and celebrities like Wade Boggs, Clint Eastwood, and Bob Dylan.
The menu is simple, with a few draft and canned beer options, or opt for the Pirate’s Punch served in a souvenir cup. This tropical rum concoction is the bar’s signature drink, so we couldn’t say no! The bartender told us that the punch got its name from the tree that grows in the middle of the bar was the site where Key West locals hung pirates disrupting their trade. It’s a delightful combination of rum, grenadine, and orange and pineapple juices. Top it off with a cherry, and you have yourself a punch fit for a pirate.

When we asked about the best place for viewing the sunset in Key West, almost everyone told us to go to Mallory Square. During the day, the location is home to shops and restaurants. In the hours before sunset, the area comes alive as hundreds of tourists descend and street performers come out to entertain the masses.
If you want that same sunset view with an incredible cocktail in hand, head to Sunset Pier. The bar connects to the Ocean Key Resort & Spa, but you don’t have to stay there to grab a drink and enjoy the live music. Just be sure to get there early to grab a table, as it fills in within the hour of sunset. We had coconut mojitos at other bars, but they were always made with coconut rum. The addition of coconut cream made this one different, giving the minty mojito a richer, fuller body.

The Smallest Bar on Duval Street lives up to its name — there are a few bar stools inside, but it’s basically standing room only. You wouldn’t want to hang out there; it’s more of a grab a drink, take a selfie, and move on type of establishment.
The Smallest Bar has a full bar, but the thing to get is definitely the shotski: four shot glasses mounted on a downhill ski. If you’re not familiar with the term, Martha Stewart famously took one with Andy Cohen. It requires coordination between your three cohorts to drink the contents without pouring them all over yourself, but it’s fun for you (and anyone passing by). You can get any liquor in the shotski, but we recommend the key lime shot — whipped cream vodka, sour mix, a splash of sprite, and key lime juice. It tastes exactly like pie and goes down dangerously easily.

You’ll want to wander to the New Town area of Key West (about two miles east of Duval Street) to get your fill of Jamaican Jerk. If you’re riding around Key West on a bicycle, the trip is easy thanks to the Florida Keys Overseas Heritage Trail that accommodates walkers and bikers as they trek along the loop around the island.
Yahman’s Authentic Jamaican Jerk Shack is located in an unassuming strip mall, sharing a space with the Sweetest Knights gift shop. You’ll know you’re in the right place if you see the picnic tables painted with the Jamaican flag and a large smoker outside. We couldn’t decide between the jerk chicken, jerk pork, and BBQ ribs, so we ordered the combo plate. It wasn’t in-your-face spicy like some jerk marinade recipes, but everything was boldly spiced. The chicken was juicy and moist, and the pulled pork was oh-so-tender. The ribs were so succulent that the bone fell right off when we picked it up!

You can’t leave Key West without a slice of the Key’s famous pie! Once you arrive at Kermit’s Key West Key Lime Shoppe, you’ll have a choice to make: Grab a slice or opt for a pie on a stick. We tried both, but the original pie was a group favorite. The pie pops are coated in dark or white chocolate, which we find takes away from the sweet-tangy flavor of the key lime juice.
If you can’t get enough of the pie, Kermit’s ships frozen pies (and the pie pops) so you can enjoy them at home. Alternatively, you can pick up the juice used to make the pies for your own key lime pie recipe at home. The shop also sells key lime-flavored cookies and candies, if you can’t get enough of the flavor.

For the iconic Duval Street bar experience, check out Hog’s Breath Saloon. The outdoor patio centers around a wrap-around bar decorated with hundreds (if not thousands) of stickers and donated license plates from around the country. The establishment also has an air-conditioned indoor seating area if you feel the need to get out of the elements.
They have all the classic island-style rum drinks, but we were in the mood for tequila, and the Hogarita caught our eye. The bartender proudly informed us that all the frozen drinks are made to order (not “batched up like at other places”), and we could taste the difference. Using Sauza Conmemorativo tequila (a woody añejo) and Patron Citronge orange liqueur delivered a sweet, smooth cocktail that cooled us down on a hot day.

Most people know about Bahamas conch, but the sea creature is famous in the Florida Keys, too. It’s featured prominently on the Conch Republic flag, which — strangely enough — represents a brief time in the 1980s when Key West declared its independence … for a mere 60 seconds.
You’ll find conch in chowder, ceviche, and on sandwiches, but the conch fritters at the Conch Shack are a great introduction to the sea snail. They look like hush puppies, but they’re filled with chewy pieces of salty conch that taste like a mix between crab and scallops. You can’t miss the restaurant’s bright yellow awning and blue-painted counter as you leave the Hog’s Breath Saloon. Order a three-, six-, or 12-piece fritters (we recommend both the key lime aioli and the spicy pink sauce) and pull up a stool to watch the team make them. Pull the first one apart when they arrive to let it cool, so you don’t torch your mouth!

There is no shortage of mojitos on Key West, a Cuban drink featuring rum, mint, sugar, lime, and soda water. Key West First Legal Rum Distillery is doing its mojito a little differently, thanks to the team’s experience making cocktails in Cuba. They even teach a mojito class to share their knowledge.
What made the mojito unique here was molasses-rich demerara sugar and quite a lot of it. Two full bar spoons of the coarse sugar went into the glass, followed by a healthy pour of key lime juice and a large stem of mint. The concoction was muddled a very specific 20 times before the glass was filled with ice, rum, and soda water. The result: a perfect balance between sweet, sour, and minty.

You’ll come across Half Shell Raw Bar as you walk along the Key West Historic Seaport, and it’s one of the best happy hour spots on the island. The restaurant has an open-air feel to it thanks to the view of the pier from almost every table, but it also captures the saloon vibe with long picnic table seating, stickers everywhere, and license plates on the walls.
Happy hour takes place every day of the week — not just on weekdays. The oysters and clams on the half shell are really the best way to go if you enjoy slurping raw shellfish, as regular pricing is based on market price, and the happy hour is quite reasonable. If raw food isn’t your thing, you can’t go wrong with their fried calamari or hot lips, the Half Shell version of jalapeño poppers.

If you need a break from seafood and Cuban food, check out Sinz Burrito, Key West’s local version of Chipotle. Themed after the seven deadly sins, this establishment has seven proteins to choose from that can be transformed into tacos, tostadas, burritos, or served in a bowl.
We tried a taco in every option — carne asada, pork carnitas, brisket barbacoa, spiced ground beef, char-grilled chicken roja, refried beans, black beans, and slow-cooked lentils. The pork carnitas absolutely stood out as the winner; although, our vegetarian friends were pretty enamored with the lentils. The variety of toppings made the tacos shine, from pickles to radishes and several salsa options (the pineapple serrano salsa was fire!). After you eat, entertain yourself with tabletop arcade games or browse the vintage record store inside the restaurant, Scorpion Records.

For a fancy sit-down dinner away from the hustle-and-bustle of Duval Street (but still close enough to walk), check out Blue Heaven. The quiet patio feels like you’ve been transported into someone’s backyard garden when you visit for breakfast or lunch, and live music transforms the space into a lively party during dinner.
It was challenging to narrow down a winner from the menu, as the fish special was perfectly cooked and the jerk chicken exquisitely spiced. But, the real star here was the heritage pork tenderloin. It was served over an insane sweet potato puree and finished with curry butter that was good enough to drink. It was a nice change from the seafood-heavy menu we’d been enjoying for the week. Ask for an extra side of cornbread to sop up any leftover juices on the plate.

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