There’s a reason why Key West has more cocktail bars than traffic lights, and it has less to do with island infrastructure than it does with our collective thirst for the perfect pour. Nothing quite beats the feeling of stepping into a dimly lit bar where the air smells like fresh citrus and aged rum, and no one will judge you for staring at the bartender’s craft like a sailor watching the horizon.
Fortunately, this island paradise has plenty of places where the drinks are as vibrant as the sunsets. Here are our favourites.
Four Marlins Oceanfront Dining
$$$ | (305) 293-6250 | WEBSITE
The team behind Four Marlins Oceanfront Dining has crafted this oceanfront spot in Key West. The menu is a “just bring me the whole spread” situation. They’ve got crab cakes with perfect crispness, grouper corn dogs that are fun little bites, and lobster mac and cheese that has the ideal cream-to-lobster ratio. It’s a rich, creamy dish, with generous lobster portions and a perfectly baked crust. Other places could never.
The filet is cooked to tender perfection, and the new Mahi dish is flaky with just the right seasoning. Crème Brûlée caps things off with its crackly top and smooth custard beneath. With friendly, attentive service and those stunning beach views, it’s worth every penny of the higher price tag for a special occasion dinner by the sea.
La Trattoria Restaurant
$$ | (305) 296-1075 | WEBSITE
Whenever we’re in Key West, the veal dish from La Trattoria Restaurant, a bustling Italian dining spot, calls to us like a siren. A plate of the tender, savory meat is the kind of hearty portion that could easily be shared—but why share when you can savor every bite? That should be your game plan at La Trattoria Restaurant.
Bel Mare Restaurant
$$$ | (305) 396-4040 | WEBSITE
Bel Mare Restaurant makes the best waterfront dining in Key West. This elegant second-floor spot has a menu with tempting homemade pastas and Michelin-quality entrees, but the best stuff is from their fresh seafood selections. Get the spectacular black grouper with stunning marina views, the linguine with clams filled with fresh ingredients and a lovely harbor backdrop, plus one of their complimentary vanilla gelato with pistachio liquor desserts to end perfectly.
Alonzo’s Oyster Bar
$$ | (305) 600-3405 | WEBSITE
Alonzo’s Oyster Bar translates as ‘time for oysters’, but to experience the best of this Key West waterfront gem, repeat after us—’time for con chowder’. In a sea of fresh oysters and crispy fried shrimp, this creamy option is a rich seafood chowder and a view of the marina, without the dipping middle man.
Berlin’s Cocktail Bar & Lounge
$$ | (305) 294-5880 | WEBSITE
Berlin’s Cocktail Bar & Lounge makes most other cocktail bars look like amateurs having a mess around with a shaker. Excellent drinks and a speakeasy-style atmosphere aside, there’s a seafood-focused menu that deserves your attention. The best things are the rich Lobster Bisque and crab cakes served with a zesty sauce, and the Oyster Rockefeller. You get a choice of cocktails and the B’s Knees and espresso martini are best.
Toasted Coconut
$ | (305) 320-0940 | WEBSITE
Poolside service rather than indoor dining is the greatest thing ever, as evidenced by the Key West Strawberry Mojito, lively atmosphere, and everything else from The Toasted Coconut. This restaurant at the north end of Key West is a great place for a craft drink first thing, breakfast dish in the morning, or lunch item midday. Things are generally acceptable, but pay attention to the unusual syrup flavor in breakfast items.
The Rum Bar
$ | (305) 296-2680 | WEBSITE
As you step off Duval Street into The Rum Bar’s cozy, character-filled space, a sense of calm washes over you. It offers a peaceful escape from the area’s busy atmosphere, with both indoor bar seating and comfortable patio areas perfect for enjoying a drink. The bar features a wide selection of rums from around the world, many of them local premium varieties, appealing to rum enthusiasts who prefer their rum to taste like rum.
Try the pina colada, rum old fashioned, or key lime martini if they’re available. The staff is friendly and helpful, often going out of their way to assist guests, especially when mishaps like spilled drinks happen. So grab a seat and plan your trip to Key West with their convenient rooms that include essentials like a refrigerator, microwave, and beach gear.
Heroes Bar and Liberty Lounge
$ | (305) 204-4991 | WEBSITE
We never thought we were bar enthusiasts until we discovered the perfect blend of rock music and cold beer at this Key West institution. It’s a lively, welcoming three-hour party, and there’s a whole lot more vibrant energy going on at Heroes: glasses of reasonably priced local brews, a historic building with charming character, and the ever-present sound of live entertainment.
The friendly staff, including bartender Mikey, makes everyone feel right at home while honoring military and first responders with genuine respect. This spot truly captures that house party atmosphere where both locals and visitors mingle effortlessly, creating memorable nights filled with good company and vibrant tunes.
The Roost
$$ | (305) 294-2600 | WEBSITE
From the moment this cozy, tucked-away Key West bar opens its doors just off Duval Street, there’s a steady hum of classic rock and clinking glasses. Settle in though—The Roost has limited seating so it feels intimate. There’s a focus on true craft cocktails, and the Old Fashioneds served on Wednesdays and the perfect cosmopolitans have a strong, balanced, and sophisticated taste. Make sure to try the Parmesan cheese plate for a savory bite.
The atmosphere during happy hour is elevated with caviar offerings and smells inviting when you walk in.
Chart Room Cocktail Lounge
$ | (305) 296-4600 | WEBSITE
At Chart Room Cocktail Lounge—a historic dive bar in Key West—you should get the free hot dogs. They’re simple and satisfying thanks to the classic preparation, and have that nostalgic flavor that pairs perfectly with a cold beer. The salty peanuts and buttery popcorn are combined with the cozy atmosphere, a wipe of the wooden bar, and a bit of local charm for moral support. You can also find the same vibe at their tucked-away location within the resort.
Virgilio’s
$$ | (305) 296-1075 | WEBSITE
Crowds gather at this Key West favorite from early evening, with patrons and palm trees eagerly lining the sidewalk for one of the famous martinis. But in a spirited twist, they aren’t the only highlight here. Instead, try the standout veal dish, phenomenal lasagna, and antipasto with fine fresh Parmesan and flavorful meats. A robust Beef Carpaccio for your appetizer is a must, too.
Liquor Store at Heroes Bar
$ | (305) 204-4991 | WEBSITE
The only thing you can count on at Liquor Store at Heroes Bar having is a crowd. Showing up to this popular Key West spot after 9pm and expecting to find a quiet seat at the bar is wishful thinking. So arrive early, or later in the evening and take whatever stool you can snag—the atmosphere’s fantastic anyway. Like the smooth mezcal old fashioned, the vibrant passionfruit margarita, and the perfectly balanced gin fizz.
Fat Tuesday Key West Duval St
$ | (305) 296-9373 | WEBSITE
The drink selection at Fat Tuesday ranges from traditional daiquiri flavors to signature mixes that can be customized with extra shots or add-ins. But it’s the Key Lime Colada at this old school bar on Duval Street that’s become a local favorite, for good reason. Served in a souvenir cup, it’s a perfect blend of tart and sweet with a creamy coconut finish.
Their outdoor patio area with a fire pit is also excellent, especially when bartenders like Savanah provide fast and friendly service while live DJ music plays in the background.
General Horseplay
$$ | (305) 741-7599 | WEBSITE
At General Horseplay, go late and get the cocktails. Inside the cozy, speakeasy-style bar near Duval Street, the sound of live music drifts from the outdoor patio, over the counter lined with hand-crafted, inventive drinks. The standout highlight is the key lime martini, topped with toasted homemade meringue and balanced with tart citrus notes. The spicy margarita is also exceptional, particularly with its perfect blend of heat and refreshment.
The bartenders, true masters of their craft, create unique cocktails beyond the menu, while the dice roll happy hour offers a fun chance to save on these excellent drinks.
Milagro Restaurant and Bar
$$$ | (305) 440-3534 | WEBSITE
We would happily order from Milagro’s menu with our eyes closed. From the rich Brisket Enchiladas to the perfectly grilled Shrimp and Scallops, the tender Octopus, and the comforting French Onion Soup—we love it all. Our perfect meal is the Petite Fillet—cooked to perfection, beautifully presented, with excellent seasoning—and a signature cocktail, perhaps one of their praised mocktails for a refreshing twist. They also offer a standout Key Lime Pie for dessert that’s a must-try.
The elegant, trendy atmosphere makes every visit feel special, whether it’s a casual dinner or a celebration. The staff provides amazing service, and the overall experience is dynamic and enjoyable, with dishes like the risotto and fresh swordfish shining brightly. We’ve returned multiple times and will keep coming back.
The White Tarpon Bar & Restaurant
$$ | (305) 851-2388 | WEBSITE
The White Tarpon is all about the three Ss: seafood, sunshine, and serenity. Landlubbers may as well sail away because there isn’t a steakhouse vibe in sight, and really it’s Florida Keys produce that gets this waterfront gem going. The menu stays reliably fresh but you can expect elevated island classics like blackened fish tacos, conch fritters, a delicious snapper sandwich, and a totally irresistible Key lime pie.
The open-air ambiance creates that perfect laid-back Key West rhythm where you’re just soaking in harbor views between bites. While the mahi sandwich hits nicely, some sides might arrive cooler than ideal—minor quibbles in an otherwise sun-drenched experience. Yes, prices float a bit higher, but between the impeccable service from folks like Becca and that ‘hook and cook’ magic where you bring your own catch, every penny feels justified.
It’s not just a meal; it’s a culinary journey through the flavors of the Keys, bon appétit and happy dining!
