Photo by Nicole Lopez-Alvar
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Well, well, well. Key West bars. Where do I even begin? In a town that’s equal parts cuckoo, quirky, magical, humble, and low-key, the bar scene embodies all of that, and then some. It’s always fun, always welcoming, and always ready to pour you something that tastes like vacation. From my first trip down the Overseas Highway to my fifteenth, I’ve never once had a bad time hopping between the legendary watering holes that make this tiny island feel like a different world entirely. Miami may be my home, but Key West is my escape. (Check out my article, “How to Spend the Perfect Weekend in Key West,” to plan your next adventure.)
Let’s start with the big guns. The Green Parrot, the oldest bar in pretty much all of Florida, founded in 1890, is one of my go-tos. Not for the barrel shots (which, to be clear, are disgusting), but for the history, the free popcorn, and the Bloody Marys that’ll cure just about anything. It’s right next to the Southernmost Point’s “0 Mile” marker, making it a perfect first or last stop. Then there’s General Horseplay, the coolest speakeasy-vibe cocktail bar in town. One of the only true craft cocktail spots on the island, it’s got a history as colorful as its drinks, and legend has it that Robin Williams even helped name the place (more on this later). And of course, Sloppy Joe’s for piña coladas with floaters, Hog’s Breath Saloon for live music and the best bar food, and Schooner Wharf Bar for unbeatable outdoor vibes and people-watching.
Part of the magic is how wildly different it feels from Miami’s bar scene. In Miami, going out can be a full-blown production: who you know, what you’re wearing, and whether you’re prepared to drop $20 on a single cocktail. Even the friendliest bar owners can’t fully offset the pressure. In Key West, there’s none of that. You can walk into a bar in flip-flops with a sunburn and still feel like a VIP. It’s our own little slice of New Orleans meets funky beach town, but only a few hours away. You don’t get this kind of laid-back magic in Sanibel, Captiva, Naples, Daytona, or Delray.
Here, you see people gathered for hours over live music, sipping piña coladas or cold drafts, fully immersed in the moment. Nobody’s glued to their phone or staging Instagram shoots; they’re actually present, soaking up the salty air, the hum of the crowd, and the rhythm of a guitar. Even when the streets are packed with tourists and bachelorette parties, there’s a calm undercurrent to Key West nightlife. You never have to dress up, you always feel welcome, and the atmosphere is one of a kind. Below, you’ll find my list of the 12 best bars in Key West, Florida, from someone who has been more than 15 times and plans to keep coming back until I’ve worn out my flip-flops.
Capt Tony’s Saloon is one of the best bars in Key West.
Photo by Nicole Lopez-Alvar
Capt. Tony’s Saloon
Capt. Tony’s Saloon is one of Key West’s most legendary bars, steeped in history dating back to 1851 when its building served as an ice house and the city’s morgue. Over the decades, 428 Greene St. has been everything from a telegraph station during the Spanish-American War to a bordello, speakeasy, and the original Sloppy Joe’s Bar (from 1933 to 1937), where the prolific Ernest Hemingway spent countless nights. In 1958, local charter boat captain Tony Tarracino bought the spot, turning it into the iconic dive where Jimmy Buffett famously got his start. Today, with bras hanging from the ceiling, a tree growing through the bar, and a mix of locals and tourists swapping stories over cold drinks, Capt. Tony’s remains a living, breathing slice of old Key West charm. 428 Greene St., Key West; 305-294-1838; capttonyssaloon.com.
Photo by Nicole Lopez-Alvar
Chart Room Bar
Tucked inside the Pier House Resort & Spa, the Chart Room Bar feels like one of Key West’s best-kept secrets. I still remember my first time trying to find it, wandering through the property until those tiny brown doors finally revealed themselves. Step inside, and it’s like walking straight into a time capsule, where a plethora of stickers, memorabilia, and dollar bills cover its wood-paneled walls, and dim lighting holds decades of island lore. Photos of a young Jimmy Buffett line the walls, as well, a reminder that this tiny bar once hosted some of his earliest performances. It’s equal parts history, nostalgia, and salty charm, the kind of place where every seat feels like it has a story to tell. Plus, it’s one of those classic dives that still serves free hot dogs, popcorn, and peanuts while you nurse a strong cocktail. You’ll never forget it. 1 Duval St., Key West, at Pier House Resort & Spa; 305- 296-4600; pierhouse.com.
General Horseplay is one of the best bars in Key West.
Photo by Nicole Lopez-Alvar
General Horseplay
For those looking to beat the heat and take a break from the tomfoolery on Duval Street, General Horseplay is one of the few true craft cocktail bars in Key West, offering a moody, sexy speakeasy vibe that feels like stepping into another world. Opened in August 2018, it’s popular for serving the best espresso martinis on the island (besides Café Marquesa) and for walls lined with quirky Robin Williams portraits, which, according to a tale told to me by a bartender, is an homage to the late actor who personally named the bar after a golf game with the owner. Beyond its top-notch cocktails made with unique, locally sourced ingredients (including fruit from Robert Is Here), the space also boasts a lively music venue in the back. With its playful history, inventive drinks, and intoxicating atmosphere, General Horseplay is a place where you can truly get lost for hours. Pro tip: Don’t miss out on the bar’s “2 Cents” happy hour (rolling the dice to determine the drink price). 423 Caroline St., Key West; 305-741-7599; generalhorseplay.com.
Green Parrot Bar is one of the best bars in Key West.
Photo by Nicole Lopez-Alvar
Green Parrot Bar
The Green Parrot Bar, the oldest bar in Florida, dating back to 1890, is a true Key West institution with a soul as colorful as the island itself. Originally a grocery store before becoming the Brown Derby sailors’ bar, it transformed in the 1970s when visionary owner Judy Sullivan turned it into one of America’s “great freak-bars,” attracting hippies, bikers, and free spirits with its open-air shutters and legendary tequila specials. Later, owners Jim and Linda Bean cemented its legacy by making live music the heartbeat of the bar, earning national recognition from Playboy in 2000 as one of “The Best Bars in America.” Today, under the stewardship of John Vagnoni and Pat Croce, the Green Parrot remains a rowdy, welcoming corner saloon where locals and tourists gather for free, old-school popcorn, the famous “Root Beer Barrel” shots (I personally am not a fan, but you gotta try it at least once), and unforgettable nights of music and memories.601 Whitehead St., Key West; 305-294-6133; greenparrot.com.
Hog’s Breath Saloon is one of the best bars in Key West.
Photo by Nicole Lopez-Alvar
Hog’s Breath Saloon
Hog’s Breath Saloon is often the very first stop on almost everyone’s Key West hit list, and for good reason: it’s pure island energy from the moment you hear the live band spilling out onto the street. Founded in 1976 in Ft. Walton Beach by Jerry Dorminy and brought to Key West in 1988, it quickly became the go-to locals’ bar on Duval Street, blending great seafood, cold drinks, and nonstop music. Its famous motto, “Hog’s breath is better than no breath at all,” has become a badge of honor for visitors who almost always leave with a T-shirt as proof they were there. With its lively crowds, infectious music, and laid-back Key West spirit, Hog’s Breath is more than a bar – it’s a rite of passage. 400 Front St., Key West; 305-296-4222; hogsbreath.com/keywest.
The popular “Cinnamon Toast Crunch” shot at Irish Kevin’s on Duval Street in Key West
Photo by Nicole Lopez-Alvar
Irish Kevin’s
Irish Kevin’s, opened on July 28, 1998, by the real Irish Kevin himself, is one of Key West’s most unforgettable bars on Duval Street. Known for live music from morning until late night, it’s a nonstop party where singing along and joining the show is highly encouraged (you can even watch a live stream of Irish Kevin’s live performances to feel like you’re there when you’ve headed back to reality). Today, Irish Kevin’s is a must-visit bar where locals and tourists alike come for great music, hearty food, cold beer, and a taste of true Key West fun. Pro tip: While you’re there, order a “Cinnamon Toast Crunch Shot” made with Fireball whiskey and Rumchata creme liquor (my favorite), or an “Irish Car Bomb.” But you can’t go wrong with any of their signature shots or cocktails. (P.S. Check out a photo of the famed Jameson chandelier further down this story.) 211 Duval St., Key West; 305-292-1262; irishkevins.com.
Mary Ellen’s Bar & Restaurant is one of the best bars in Key West.
Photo by Nicole Lopez-Alvar
Mary Ellen’s Bar & Restaurant
Owned by the folks behind the aforementioned General Horseplay, you already know this neighborhood dive bar is going to be great. Mary Ellen’s Bar & Restaurant is the kind of Key West dive where the beer is cold, the music is loud, and something hilarious is probably happening at the bar. Just off Duval Street on Appelrouth Lane, it’s the perfect spot to escape the heat, sink into the AC, and dig into comfort-food favorites like gooey grilled cheese, crispy wings, and golden tater tots. Nights here are anything but predictable, with live music, DJs, sports on TV, and offbeat events like the infamous “charity vibrator races” (yes, it’s a thing). And the best part? It’s one of the only indoor dives in Key West where your dog can belly up to the bar with you. Pro tip: Order the “Frozen Irish Cream” with Oreos…served with a spoon. It’s divine. 420 Appelrouth Ln., Key West; 305-294-7750; maryellensbar.com.
A margarita at Schooner Wharf Bar in Key West’s Historic Seaport
Photo by Nicole Lopez-Alvar
Schooner Wharf Bar
Schooner Wharf Bar is a legendary slice of old Key West, perched right on the Historic Seaport where the island’s spirit comes alive. Since 1984, this funky open-air spot, built on the site of the old Singleton Shrimp Factory, has drawn locals and visitors with fresh seafood, top-notch live music, and a laid-back vibe that’s pure paradise. From breakfast on the bight to late-night drinks, it’s a place where sailors, locals, tourists, and even pets mingle under the sea breeze. With its mix of history, flavor, and unforgettable characters, Schooner Wharf isn’t just a bar; it’s a Key West tradition. Pro tip: It’s a great place to bring the family because it’s not as rowdy as some of the others on this list. Plus, it has great sunset views. They also have nearly ten types of mojitos, fun shots, and signature cocktails like the “Schooner Breeze.” 202 William St., Key West; 305-292-9520; schoonerwharf.com.
Sloppy Joe’s in Key West on Duval Street
Photo by Nicole Lopez-Alvar
Sloppy Joe’s
Sloppy Joe’s is more than just the most famous bar in Key West – it’s the island’s beating heart and a living piece of its history. Officially opened on December 5, 1933, the day Prohibition was repealed, by legendary rumrunner and charter boat captain Joe Russell, it became Ernest Hemingway’s favorite watering hole and the gathering place for his colorful “mob” of writers, artists, and locals. In true Key West fashion, the entire bar was famously moved, drinks and all, down the street to its current location at Duval and Greene in 1937 over a one-dollar rent dispute. Today, Sloppy Joe’s remains the most beloved and visited bar in town, drawing crowds from around the world for its live music, strong drinks, and that undeniable magic that only comes from nearly a century of legendary stories. Pro tip: Order the piña colada with a rum floater. I don’t know why they’re so damn good here. 201 Duval St., Key West; 305-294-5717; sloppyjoes.com.
The Smallest Bar in Key West on Duval Street is tiny but mighty.
Photo by Nicole Lopez-Alvar
Smallest Bar
The Smallest Bar in Key West, which opened in 1998 on Duval Street, proves that size means nothing when it comes to having a good time. Despite its tiny footprint, it’s legendary for its unbeatable vibe, prime location, and the way it instantly charms anyone you bring along. Bartenders here are famously friendly, and it’s not unusual to find college kids laughing over “shotskis” right on the sidewalk. Whatever you do, order the key lime pie shots – they’re delicious, dangerously smooth, and pure Key West in a (tiny) glass. 124 Duval St., Key West; smallestbar.com.
Sunset Pier is one of the best bars in Key West.
Photo by Nicole Lopez-Alvar
Sunset Pier
Although this is definitely one of the more touristy spots on this list, the live music here is unreal, with a sunset view right on the pier facing Sunset Key. Thanks to its unbeatable location on Sunset Pier, just steps away from Mallory Square with jaw-dropping ocean views, sipping a cocktail here while the sun melts into the horizon feels like pure island magic. Plus, there’s always live talent crooning away. This is pure laid-back Key West charm, and it makes for a great photo opportunity for friends and family members. 0 Duval St., Key West; 305-296-7701; oceankey.com/key-west-sunset-pier.
Willie T’s is one of the best bars in Key West
Photo by Nicole Lopez-Alvar
Willie T’s
Willie T’s is one of the best bars in Key West, famous for its lively atmosphere (you can hear it from blocks away) and walls covered with signed dollar bills from visitors around the world. The energy here is nonstop, with live music spilling onto Duval Street day and night. And, of course, you can’t skip their legendary margaritas, which are so big they’re literally larger than your head. 525 Duval St., Key West; 305-294-7674; williets.com.
Bonus Photos for Your Pleasure:
Photo by Nicole Lopez-Alvar
Inside Capt. Tony’s Saloon, bras and dollar bills hang from the ceiling beside the trunk of a real-life tree.
Photo by Nicole Lopez-Alvar
The famous Jameson Chandelier at Irish Kevin’s bar on Duval Street. Gotta love the Conch Republic.
Photo by Nicole Lopez-Alvar
A very NSFW (not suited for work) collage of printed photographs from over the past several decades on display at the legendary Chart Room Bar. If you look closely, you’ll see a few photos of the late Jimmy Buffett.
