Top Local Bars in Key West: The Ultimate Guide to Island Nightlife
When the sun dips low over Key West, Duval Street lights up like a neon paradise. Every night feels like a party here – Key West nightlife is an experience you have to feel to believe. Picture yourself strolling down Duval with warm ocean breezes on your face, live music spilling from open doorways, and the laughter of locals and travelers mingling together. In this ultimate bar-hopping guide, I’ll take you on a tour of the 10 best bars in Key West – from legendary haunts to quirky dives, a rooftop oasis, and hidden local favorites. Grab a drink (or two) and let’s hit the town, conch (Key West local) style!
We’ll start in the heart of Old Town on Duval Street and work our way through famous watering holes and secret spots only the locals know. Along the way, you’ll soak in everything from rowdy live music joints to laid-back tiki bars with killer sunset views. Ready? Follow me – this local’s got the lowdown on where to drink in Key West for an unforgettable night out.
(Remember to pace yourself – Key West pours are generous and the fun goes late. Take advantage of happy hours, drink plenty of water, and above all, enjoy responsibly!)
Sloppy Joe’s Bar
Inside the legendary Sloppy Joe’s – where live music, strong drinks, and Hemingway history collide on Duval Street. A must-stop for classic Key West nightlife and rowdy good times!
Atmosphere/Vibe: Lively, historic, and rowdy Duval energy with live music all day and night. Sloppy Joe’s is almost always packed – a rollicking mix of tourists and locals singing along to the band and dancing with strangers. This place has been “the life of the party” in Key West since the 1930s.
What Makes It Special: Sloppy Joe’s is Key West history. It opened the day Prohibition ended in 1933 and quickly became the favorite hangout of Ernest Hemingway. The walls are covered in vintage photos and Hemingway memorabilia, and each July the bar hosts the famous Hemingway Look-Alike Contest during Hemingway Days. Sloppy Joe’s is listed on the National Register of Historic Places and remains the icon among top Duval Street bars. Beyond the history, it’s just plain fun – there’s live music from noon ‘til 2am every single day, and the crowd is always in a partying mood. You can literally watch the action on their live webcams when you’re not there!
Top Drink(s) to Try: Start with their award-winning Sloppy Rita margarita – a tangy, refreshing tequila cocktail that’s a house specialty. If you’re a Hemingway fan, try the “Papa Dobles” daiquiri (Hemingway’s legendary rum drink). Of course, you can never go wrong with a cold draft beer or their classic rum runner either. Don’t forget to toast “Papa” Hemingway while you drink!
Address: 201 Duval St, Key West, FL 33040 (at the corner of Duval & Greene)
Captain Tony’s Saloon
Atmosphere/Vibe: A quirky dive bar with tons of character (and characters!). Captain Tony’s is dimly lit, delightfully shabby, and utterly authentic – this is the oldest bar building in Key West. You’ll often find a local guitarist strumming in the corner or patrons tossing coins onto a coffin in the floor. Yes, really – it’s that kind of place!
What Makes It Special: If these walls could talk, you’d hear wild tales. Captain Tony’s was the original Sloppy Joe’s Bar where Hemingway drank in the 1930s. After Sloppy Joe’s moved to Duval, owner Captain Tony (a colorful Key West legend who was once mayor) opened his namesake saloon here. The decor is infamous: business cards and dollar bills plaster every surface, bar stools are decorated with bras left by past patrons, and there’s a giant tree growing through the roof (it used to be the town hanging tree, as legend has it). This historic dive bar has hosted everyone from Hemingway to Truman Capote. It’s unapologetically rough around the edges and full of Key West charm.
Top Drink(s) to Try: You must try the Pirate’s Punch, Captain Tony’s signature rum punch that comes in a souvenir cup – sweet, strong, and dangerous (in a good way). It’s their “original” cocktail and goes down smoothly on a hot tropical night. If sweet punches aren’t your thing, grab an icy beer or a simple rum and coke. The point here isn’t fancy mixology – it’s soaking up the atmosphere with a cold drink in hand. Take your cup outside to the courtyard or plop down at the bar and chat with the friendly bartenders.
Address: 428 Greene St, Key West, FL 33040
The Green Parrot
Inside the legendary Green Parrot – a sunny place for shady people!
Atmosphere/Vibe: A true locals’ bar with a laid-back, funky vibe. The Green Parrot is loud, unpretentious, and ridiculously fun. It’s just off Duval on Whitehead Street, and you’ll often find the doors and windows wide open, live rock or blues music blasting, and a crowd dancing like nobody’s watching. Think dive bar meets live music venue – neon beer signs, a pool table, darts, and a strict “no sniveling” motto on the wall.
What Makes It Special: The Green Parrot is nothing short of a Key West icon – it’s been around since 1890! This is the kind of bar where locals go after work and visitors who wander in feel like they’ve discovered a secret. Every night, great live music and “original beverages” (try their oddball house shots) mix with a merry gang of Conch regulars and open-armed tourists to create pure Key West magic. Over the years it’s hosted hurricane parties, divorce parties, pet birthday parties – you name it. The ceiling is draped in a parachute, the décor is delightfully eclectic (check out the smirking cartoon parrot mural), and the vibe is “come as you are and be yourself.” Everyone is welcome here, and by the end of the night you’ll feel like family.
Top Drink(s) to Try: Two words: Root Beer Barrel. This is The Green Parrot’s signature shot – root beer schnapps dropped into beer – a weird-sounding combo that’s shockingly tasty and a local tradition. Order a round for your group and toast to “no sniveling!” They also pour a great Dark & Stormy (rum and ginger beer) and often have unique craft beers on tap. Happy hour is daily 4–7pm, so swing by for a discounted beer before the late-night crowd hits.
Address: 601 Whitehead St, Key West, FL 33040
Hog’s Breath Saloon
Atmosphere/Vibe: Classic open-air bar with live music and a party patio. Hog’s Breath Saloon sits at the corner of Duval and Front Street and always has something going on – whether it’s a local band jamming on the outdoor stage or folks browsing the famous Hog’s Breath t-shirt shop attached to the bar. The vibe is come-as-you-are, a bit touristy but also beloved by many locals for its reliable good times. Expect a mix of people kicking back at picnic tables outside, dancing by the stage, or cooling off in the indoor bar’s A/C.
What Makes It Special: “Hog’s breath is better than no breath at all!” This legendary slogan pretty much captures the bar’s cheeky spirit. Hog’s Breath has been entertaining Key West for over three decades and remains one of the island’s favorite spots. It’s famous for its live webcam (friends back home can watch you party in real time), its huge selection of branded merch, and non-stop live entertainment. They feature top local bands and even nationally touring acts on their stage every day and night. There’s a bit of a tropical roadhouse vibe – lots of license plates and dollar bills tacked up, strings of lights, and the constant flow of laughter and music. If you’re doing the “Duval Crawl” (a bar crawl down Duval Street), Hog’s Breath absolutely deserves a stop on your list of top Duval Street bars.
Top Drink(s) to Try: Cool off with a Hogarita (their Key Lime margarita twist) or the famous Hog’s Breath Lager, a house beer that’s crisp and easy-drinking. Another local favorite is the Hogwash – a mango rum punch that captures the taste of the Keys (and packs a punch!). They also make a mean Key Lime Pie cocktail (sweet and creamy). Happy hour is typically 5–7pm with specials on drinks. And if you need a snack, their Conch fritters or fish dip pair perfectly with that cold beer.
Address: 400 Front St, Key West, FL 33040
Schooner Wharf Bar
Atmosphere/Vibe: An open-air dockside bar that oozes Old Key West charm. Schooner Wharf sits on the Historic Seaport, right beside the marina’s tall ships, giving it a chill, nautical vibe. Think breezy patio under tiki huts, dogs lying at their owners’ feet, live musicians strumming island tunes, and a view of yachts bobbing in the harbor. It’s super laid-back – the motto here is “The Lower 40… Feet” (as in, just get barefoot and relax).
What Makes It Special: They call Schooner Wharf “the Last Little Piece of Old Key West” for a reason. This beloved bar feels worlds away from the bustle of Duval. You can watch the sunset paint the sky and see schooner ships sailing by as you sip your drink. It’s the kind of place where time slows down. Schooner Wharf is also famous for its colorful events – from minimal regatta parties to the insane “Minimal Regatta” (where people race boats made of plywood and duct tape). The bar is pet-friendly and super casual – don’t be surprised if a parrot (the feathered kind) is hanging out with its owner at the bar. Longtime visitors rave that “this must be the center of the universe” when they’re here, and once you experience the easygoing magic of Schooner Wharf, you’ll know why.
Top Drink(s) to Try: Embrace the island vibe with a Painkiller – a classic rum, pineapple, and coconut cream cocktail that originated in the islands (topped with nutmeg). They make a great one, perfect for a hot afternoon. Another winner is the Pirate’s Punch (a fruity rum punch served in a souvenir cup). If frozen drinks are calling your name, grab a Rum Runner or Key Lime colada from the blender. Happy hour here is often late morning to early afternoon – yes, morning – making it a great first stop to kick off day drinking. Pro tip: the bar opens for breakfast drinks, so you can even start your day with a Bloody Mary by the docks (it is Key West, after all!).
Address: 202 William St, Key West, FL 33040 (at the Historic Seaport)
The Bull & Whistle (and Garden of Eden)
Outside The Bull & Whistle – open-air drinks, live tunes, and people-watching from the balcony above Duval. Look up… the rooftop’s where things really get wild!
Atmosphere/Vibe: Three levels of classic Key West bar craziness. The Bull & Whistle is an open-air bar on the ground floor (The Bull), a slightly more mellow pub with a balcony on the second floor (The Whistle), and – wait for it – a clothing-optional rooftop bar on the third floor (the notorious Garden of Eden). The overall vibe: fun, a bit wild, and totally come-as-you-are (or come as you aren’t, in the rooftop’s case!). Downstairs at The Bull, you’ll usually find live music (often acoustic or rock) with people dancing in the open windows facing Duval. Upstairs at The Whistle, folks chill with pool tables, darts, and a people-watching balcony overlooking Duval Street. And upstairs… well, anything goes!
What Makes It Special: The Bull & Whistle is a Duval Street institution. It’s one of the last old-school open-air bars on Duval, and it really gives you that tropical nightlife feel with breezes blowing through as you sip your drink. It’s actually two bars in one: the rowdy live-music scene at The Bull, and a sports bar vibe at The Whistle (with TVs often tuned to the game). But what really makes it special is the Garden of Eden rooftop. Few bars can claim a clothing-optional sun deck under the stars! If you’re feeling daring (and over 21), you can venture up to the third floor where patrons are known to shed a layer or two and paint their bodies during festivals. Even if you keep your clothes on, it’s worth a peek for the view and the sheer novelty. This trifecta of bars means there’s something for everyone, all in one historic building at Caroline & Duval.
Top Drink(s) to Try: Keep it simple and order a beer or rum punch – drinks are strong and affordable here, and there are often two-for-one specials during happy hour (usually 5–7pm). Many swear by the whiskey shots at The Bull while dancing to live music. If you head to the rooftop, try a Garden of Eden specialty cocktail – the bartenders sometimes whip up fun concoctions during Fantasy Fest and Pride Week when the rooftop gets busy. Honestly, the draw here isn’t craft cocktails but the atmosphere. Grab a cold Bud Light or a rum and Coke, and soak in the Key West madness.
Address: 224 Duval St, Key West, FL 33040
Irish Kevin’s
Atmosphere/Vibe: High-energy Irish pub meets comedy club. Irish Kevin’s is famous for its raucous live entertainment – usually one of their hilarious musician/hosts on stage playing guitar, singing, and playfully roasting the audience. The vibe is party central: bar-goers singing along to Irish drinking songs and ’90s covers, people chugging beers on stage, and an all-around boisterous crowd. If you want to laugh, sing, and possibly end up on stage doing a jig, this is your spot.
What Makes It Special: Located right on Duval, Irish Kevin’s has been a Key West staple since 1998. It prides itself on being a “rustic second home” to its guests – and indeed, many people end up spending entire nights here because it’s just so fun. The bar’s entertainers are legendary for involving the crowd in their act (don’t be shy if they call you out – it’s all in good fun). By the end of the night, you might find yourself chanting along to “Sweet Caroline” with 100 new friends. The staff is super friendly (and often very witty), making everyone feel welcome. And as the name suggests, it’s an Irish pub at heart – so expect the best Guinness pour in town and maybe even an impromptu Irish jig on the bar. Irish Kevin’s truly embodies “Key West happy hour” vibes that extend well into the wee hours.
Top Drink(s) to Try: It’s all about the beer and shots here. Grab a pint of Guinness – they pour it properly, with that perfect creamy head. If you’re more into cocktails, the Irish Car Bomb (a shot of Irish cream and whiskey dropped into a half-pint of Guinness) is a crowd-pleaser – and usually, the entertainer on stage will make a whole show of it if someone orders one! They also have a full liquor bar, so you can get anything from a Jameson Irish Whiskey neat to a fruity Key West cocktail. But honestly, an ice-cold beer or a simple whiskey ginger feels right in this rowdy pub. Sláinte!
Address: 211 Duval St, Key West, FL 33040
Willie T’s
Inside Willie T’s – mojitos flow, dollar bills cover every surface, and live music keeps the tropical vibes going strong. A breezy, come-as-you-are Duval Street classic!
Atmosphere/Vibe: Outdoor tropical bar with live music and a one-of-a-kind décor. Willie T’s is completely open-air – essentially a big patio bar right on Duval – and it’s almost always jamming with live music, day and night. What immediately catches your eye are the dollar bills literally wallpapering the entire place (there’s said to be over $100,000 in singles stuck to the walls and ceiling!). The vibe is fun, breezy, and welcoming – you can wander in off the sidewalk and grab a seat in the shade while a singer-songwriter plays your favorite Jimmy Buffett tune. It’s the perfect spot to sit back with a cocktail and people-watch the Duval Street action.
What Makes It Special: Willie T’s is a local legend for its constant live music and its money-covered walls. Adding a signed dollar bill to the collection is almost a rite of passage for visitors – see if you can spot bills from all over the world fluttering above. The bar is named after one of Key West’s famous rogues, but these days it’s renowned for its “famous mojitos” and a come-as-you-are vibe. This bar truly embraces the Key West spirit: tropical, a little tacky (in a good way), and all about having a good time. It’s also pet-friendly and great for groups. By afternoon, the live musician has folks clapping along, and by night, it can get quite lively with the Duval crawl crowd joining in. It’s open late, but I especially love Willie T’s in the early evening – catching happy hour with a mojito in hand as the sun sets and the singer croons, “Don’t worry, be happy.”
Top Drink(s) to Try: Mojitos, mojitos, mojitos! Willie T’s is famous for them – muddled fresh with lots of mint and a hit of rum. Try their classic Mint Mojito or mix it up with a Mango Mojito. They even do a Champagne Mojito for something extra festive. Also popular are their Rum Runners, which are almost as renowned as the mojitos. During happy hour (daily 4–7pm), they often have 2-for-1 drink specials, so you can sample a couple different cocktails. If you’re hungry, their menu of bar bites (conch fritters, fish tacos, etc.) will keep you fueled for more drinks. And here’s a fun tip: if you order a shot, ask for the “bell” – they’ll ring a ship’s bell behind the bar and get everyone’s attention as you throw it back!
Address: 525 Duval St, Key West, FL 33040
Sunset Tiki Bar & Grill (at The Galleon Resort)
Atmosphere/Vibe: A hidden gem tiki bar with front-row seats to the sunset. Tucked behind the Galleon Resort, Sunset Tiki is perched on the harbor’s edge – literally “where the boardwalk ends and the sunset begins”. The vibe is chill and friendly, with a thatched-roof tiki hut bar, palm trees, and the sound of waves lapping nearby. By day, it’s a quiet hideaway to sip a cocktail by the pool; by evening, it transforms into a magical sunset spot with live tropical music nightly and a mix of locals and savvy tourists clinking glasses as the sky explodes in color. It’s off the typical Duval Street path, which makes it feel like you discovered a secret island oasis.
What Makes It Special: Two words: Sunset views. Sunset Tiki Bar boasts one of the absolute best views of Key West’s famous sunset, without the crowds of Mallory Square. As you relax on the deck, you can watch the sun melt into the Gulf right between the marina’s boats – pure bliss. The bar is often called the “ultimate hidden gem” of Key West. It’s popular among locals (especially boaters and the resort’s guests), and many don’t even know it’s open to the public – but it is! They even have two happy hours daily (one early, one late), so you can enjoy discounted drinks as you soak in the scenery. The atmosphere is super laid-back: think hammocks, tiki torches, maybe a gentle steel drum or acoustic guitar playing. If you need a break from the Duval madness, this is your sanctuary.
Top Drink(s) to Try: Embrace the tiki vibe with a Mai Tai or the house Rum Runner – both fruity, boozy classics that taste like vacation in a glass. They also serve a popular layered frozen drink called the “Pain in the A” (half piña colada, half rum runner – a frozen striped delight that’s a Florida Keys staple). At sunset, I love to order a Golden Margarita or their Key Lime Martini – something about watching the sunset with a limey cocktail feels so Key West. Also worth trying is the Havana Banana (a creamy banana rum drink) if they have it. Keep an eye out for daily specials; the bartenders here are known to whip up creative concoctions. And if you’re hungry, their grill serves up tasty fish sandwiches and conch fritters – perfect to nibble on as the sun goes down.
Address: 617 Front St (The Galleon Resort docks), Key West, FL 33040
The Rum Bar at the Speakeasy Inn
Atmosphere/Vibe: An intimate front porch bar that’s all about the rum and the relaxed vintage vibe. The Rum Bar is located on the porch of the Speakeasy Inn (a historic old Key West house on upper Duval), and it feels like sipping drinks at a friend’s cozy verandah. With just a few bar stools and some porch seating, it’s a quiet retreat from the hustle – you’ll hear soft reggae or jazz playing, and you can watch the world stroll by on Duval Street under the shade of palm fronds. It’s usually manned by a single expert bartender who’s ready to talk rum and mix you something fabulous.
What Makes It Special: This hidden local favorite is renowned for its incredible rum collection – the largest on the island, in fact. Rum enthusiasts consider it a must-visit. The bar is actually inside a former cigar factory owner’s home from the 1920s, adding to the speakeasy vibe. It’s got an old-school charm with its wooden bar and tropical decor. What I love most is the personal touch: with just a handful of patrons at any time, you end up chatting with the bartender (who might tell you some Key West stories) or striking up conversation with fellow travelers. It feels exclusive yet completely unpretentious. You get the sense you’ve discovered a secret Key West happy hour spot that most on Duval Street walk right past. And indeed, many people do – which is fine, more rum for us!
Top Drink(s) to Try: Rum, of course! The Painkiller here is legendary – rich, creamy, and topped with fresh nutmeg, it transports you straight to the British Virgin Islands. The Dark ’n Stormy (Gosling’s dark rum with ginger beer and lime) is another classic they nail, perfectly balanced and refreshing. But honestly, ask the bartender for a recommendation – they might pour you a taste of a rare single-barrel rum or craft you a bespoke cocktail based on your preferences. If you’re a rum aficionado, you can also order a rum flight to sample a few neat pours from their extensive collection. Non-rum drinkers, fear not: they’ll whip up a great Key Lime Mojito or even a classic Martini if you ask. Sipping a top-notch cocktail on this little porch while watching the lazy Duval Street foot traffic – that’s Key West heaven.
Address: 1117 Duval St, Key West, FL 33040 (at the Speakeasy Inn, upper Duval)
Wrap-Up: From the famous neon lights of Sloppy Joe’s to the quiet porch of the Rum Bar, Key West offers a bar scene as colorful as a tropical sunset. Whether you’re craving the best bars in Key West for live music and dancing, or seeking out Key West’s happy hour spots to sip a cocktail by the water, this island delivers in spades. The common thread? An attitude of “no worries, no hurry” and a genuine camaraderie – you’ll leave each of these bars with a story to tell and maybe a few new friends.
As your local guide, my best advice is: embrace the spirit of the island. Mix and mingle. Try the weird house shot. Dance like nobody’s watching. Drop a dollar on the wall. And definitely catch at least one sunset with a drink in hand. This is what Key West nightlife is all about – fun, free-spirited, and a little wild.
Finally, enjoy responsibly. The drinks here can be strong (and the nights long), so know your limits and stay safe. Most of these bars are walking distance or a short taxi ride from each other – no need to drive. When you’re done bar-hopping, you might even find a late-night slice of Key lime pie calling your name as a nightcap.
Got a favorite Key West bar or a fun Duval Street memory? Leave a comment! I’d love to hear your own tips on where to drink in Key West. Until then, cheers – or as we say down here, cheers y’all! Enjoy your Key West nights, one fabulous bar at a time. 🌴🍹
