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Live The Nightlife: 18 Best Bars In Key West

best bars in key west

After basking in the gorgeous sunsets and enjoying the laid-back island atmosphere, it’s time to live the nightlife and explore the best bars in Key West. When the sun sets, the streets come alive with laughing, clinking drinks and the irresistible rhythms of live music. 

This article will guide you through the 18 best bars in Key West, from quiet speakeasies to boisterous beachside clubs, offering an amazing evening experience for visitors and locals alike. So put on your dancing shoes and dresses, and join us as we explore the lively nightlife of Key West.

The Nightlife in Key West: Introducing The Best Bars

The nightlife in Key West is unlike any other. It’s a thriving and diversified environment that caters to various tastes and preferences. The island is relaxed and welcoming, with a distinct blend of charm and excitement. The streets come alive with activity as the sun sets over the blue ocean.

Key West is also known for its vibrant bar culture, which offers a diverse selection of options. There’s a pub for every mood, from vibrant seaside bars with breathtaking views to small and quaint speakeasies tucked away in the ancient Old Town. Many pubs have outdoor seating, so patrons may enjoy the balmy tropical nights while sipping their favorite cocktail.

Sunset Pier

 

Sunset Pier on Duval Street offers a mesmerizing environment where stunning sunsets and exciting nightlife perfectly mix. As the name implies, this popular area is well-known for providing a front-row seat to the breathtaking sunset views over the Gulf of Mexico. The pier reaches out into the blue waters, providing a panoramic picture that is nothing short of breathtaking.

Sunset Pier’s cocktails are as refreshing as the coastal wind. You can enjoy a range of tropical libations while relaxing in one of the nice outdoor dining spaces. Drink a Key Lime Hard Cider or try frozen cocktails with a shot of dark rum. The cocktails wonderfully suit the laid-back island ambiance and perfectly complement the stunning sunset views.

Favorite menu item: Peel & Eat Key West Pink Shrimp – poached in crazy lady beer and spices, cocktail sauce, lemon

Sloppy Joe’s

Sloppy Joe’s by Key TV

  • Location: 201 Duval St, Key West, FL 33040
  • Price: $$ – $$$
  • Website: sloppyjoes.com

 

Sloppy Joe’s is one of Key West’s most well-known bars. It is best recognized as Ernest Hemingway’s favorite drinking establishment. Hemingway even came up with the name Sloppy Joe’s. Joe Russel, the owner, was a boat skipper and Hemingway’s acquaintance. Hemingway proposed that Joe rename the establishment Sloppy Joe’s after a Havana tavern.

This Key West pub opened on December 5, 1933, but was relocated to its current position on the corner of Greene and Duval in 1937. Sloppy Joe’s also hosts the annual Hemingway Look-Alike contest, in which thousands of hopefuls fight for the title of “Papa.” White-bearded Hemingway aspirants form a line and participate in challenges to acquire the coveted prize. This competition has been ongoing since 1981 and is a big hit.

Even on a random Monday night, it is always busy. Sloppy Joe’s has a dance floor set up from 9:30 PM with live music until 2:00 AM, so those still standing can practice their dance moves. 

Sloppy Joe’s is on everyone’s list of things to do in Key West, whether for a drink or a sandwich. Come in the late afternoon to avoid the crowds, or stop by Joe’s Tap Room for a selection of draft beers on tap. If you want to party late, you’ll likely end up here.

Favorite menu item: Sloppy Joe Sandwich – Delicious ground beef in a sweet rich tomato sauce, with onions, peppers and spices

Green Parrot Bar

green bar parrot
  • Location: 601 Whitehead St, Key West, FL 33040
  • Price: $$
  • Website: greenparrot.com

 

Despite its proximity to Duval, Green Parrot has a more local vibe and is ideal for a chilled beer in a relaxed ambiance. For almost 125 years, it has graced the landscape of Key West. 

The Green Parrot is also known as the “Last Bar on US Highway 1.” It is housed in one of the island’s oldest venues. The bar started as a grocery store, but when the war brought in sailors, the grocery store began slinging drinks… and the rest is history. 

Drinks and a jukebox keep the mood lively during the day, but live bands and the once-a-month ukulele club add a more cheerful island flavor at night. 

Green Parrot is constructed of wood, as are the stools, and the décor is classic Americana, with flags and tons of musical memorabilia. It is undoubtedly Key West’s best dive bar, where locals frequently hang out, and one of the top bars in the Florida Keys.

Favorite menu item: Free popcorn – technically, this is not on the menu but patrons are raving about it! 

Captain Tony’s Saloon

Capt. Tony’s Saloon in Key West, Florida by Bars, Beers, and Breweries

 

Captain Tony’s Saloon is a historic institution where you can sip a beer. It is the oldest tavern in Key West and the oldest pub in Florida. 

Captain Tony was a former mayor of Key West and a fishing boat captain. This historic pub was built in 1851 as an icehouse. This is the original location of Sloppy Joe’s, the favorite pub of Tennesse Williams, and Ernest Hemingway was frequently spotted at a barstool here until the late 1930s when he left Key West.

The ceiling is one of the first things you’ll notice when you walk in. Hundreds of business cards, registration plates, and bras cover everything! Enjoy beers at the bar and a wide range of high-quality live music every night. Ask the bartender about the “hanging tree” that’s growing right through the center of the bar for some pirate mythology. (Hint: It’s where 19 pirates were executed.) Jimmy Buffet got his start in the dismal bar as well. If you need help deciding what to order, the Pirate Punch, the bar’s signature drink, is a good place to start.

Throw a quarter into the fish’s mouth over the door as you enter or exit; the rumor is that good luck will follow you while you are in Key West.

Favorite menu item: Captain Tony’s Amber Ale – custom-brewed on tap and patrons say it’s flavorful 

Bull & Whistle Bar

The Bull & Whistle Bar by Key TV

  • Location: 224 Duval St, Key West, FL 33040
  • Price: $$
  • Website: bullkeywest.com

 

Bull & Whistle boasts two drinking levels: stay below for easy access to Duval Street, or walk upstairs for a sports bar vibe complete with darts and a pool table.

The Bull and Whistle is Key West’s oldest open-air tavern. It is ideal for groups of friends because it has so many elements. The second-floor balcony is one of the outstanding features of this establishment.

Once inside, take a seat and observe the artwork depicting Duval Street’s daily occurrences. The Bull on the ground floor is dominated by a large central bar with a tiny performance stage in the corner, whilst the Whistle on the second floor is more of a sports bar with a pool table, darts, and other bar games. The Whistle’s short second-floor balcony, lined with stools so customers can enjoy a cool drink and the street panorama below, is definitely the greatest element of either.

Smallest Bar

A quick video on the Smallest Bar in Key West by Chasing Beaches

 

The Smallest Bar In Key West, with only a few barstools, is a delightful location for a quick drink as you go down Duval Street. If there are ten of you, the venue will be packed, and only three of you can sit. It’s right on Duval and worth a stop but move on after a drink to give others a chance. 

This is one of the Duval Street bars you’ll most likely pass by. This is due to the fact that this establishment is only 72 square feet in size, earning it the moniker “Key West’s Smallest Bar.” This is a great place to hang out with pals because you’ll have the entire bar.  

This little bar is located across the street from the Smallest Bar Inn, a normal-sized hotel. There are lots of interactions with curious Duval Street passers-by. Over the years, many renowned people have come by for a drink. Look at the names on the barstools that dangle above the bar!

Rick's Bar

ricks key west

 

Rick’s eight-in-one concept is more of an entertainment complex than a pub. The flagship, Rick’s, is a traditional tavern with late-night karaoke. Rick’s Loft is a posh cocktail club, whereas Rick’s Tree Club, a rooftop location, serves fruity cocktails with views of Duval Street below. 

Every night of the week, you may have a completely different experience. Of course, there are calmer and more intimate locations (not to mention wilder ones) across Key West, but that’s not why you’re here. It’s ideal for a larger group, such as a guys’ weekend or a bachelorette party.

Favorite menu item: Pizza – aside from being a great bar, it’s also a great pizza place!

Durty Harry

durty harry key west

 

Durty Harry’s, which is part of the famed Rick’s Bar (which is actually numerous bars all in one), is a significant draw because of its regular rock bands performing each night. This is a wonderful option if you have a boisterous bunch that wants to be rowdy. 

During peak season, Durty Harry’s is one of the greatest bars on Duval Street.  The bar serves simple cocktails and beer, but the dancing and singing crowd keeps you entertained for hours.

The DurtBags cover a wide range of tunes, except for “Freebird,” which requires a $400 tip. Many consider The DurtBags to be Florida’s best rock cover band. You may enjoy the sports bar ambiance and frenetic atmosphere in addition to the live music.

El Meson de Pepe

el meson de pepe key west
  • Location: 410 Wall St, Key West, FL 33040
  • Price: $$ – $$$
  • Website: elmesondepepe.com

 

El Meson De Pepe’s Restaurant & Bar is a Mallory Square staple for sunset drinks and Cuban cuisine. If you prefer Cuban food and cocktails, this is the best bar in Key West. Views of Mallory Square and the Gulf of Mexico make this a fun place to visit.

What’s even better is that as you wander about Mallory Plaza, watching the performers and admiring the sunset, El Meson De Pepe has a sidebar offering delicious mojitos that you can consume while strolling around the plaza. 

El Mason De Pepe is a flamboyant celebration of all things Cuban and the best destination in Key West for Cuban food. It’s ideal for couples or small parties. Make sure you come hungry because the cuisine is delicious!

Favorite menu item: Plantain Chips – almost everything on the menu can be served with these fried ripe, sweet plantains as a side. 

The Waterfront Brewery

the waterfront brewery key west

 

Choose a table with a view of the water at the Waterfront Brewery and purchase one of their craft beer sample flights. For beer enthusiasts, this place is a must-visit in Key West. The bar offers a happy hour every day between 4:00 and 6:00 PM.

Key West residents adore Key Lime Pie, but a beer? This beer, made with Key Lime juice, is mildly tangy with a long vanilla finish. You must give it a shot!

Favorite menu item: Shrimp & Scallop Risotto – jumbo shrimp and seared sea scallops over creamy risotto with fresh basil, parmesan cheese, and white wine butter sauce

Little Room Jazz Club

best bars in key west jazz club

 

The Little Room Jazz Club is great for a sophisticated night out in Key West. This club is the ideal bar if you want to get away from the hustle and bustle of Duval Street. Five nights a week, live jazz is performed.

The blue-lit stairs leading to the Little Room Jazz Club will let you know you’ve arrived. This intimate space has everything you want in a music club: talented performers, an above-average cocktail menu, sleek seating, and a sexy, candlelit look that fits the sultry sounds onstage. If you prefer your music to be heard in the background, there are a handful of small nooks farther away from the stage and some outdoor seating. 

The wine and beer selections are vast, but most customers choose cocktails: a house specialty is Hemingway’s Death By Champagne, a Champagne cocktail with absinthe bitters, lemon, and Lillet Blanc. All of this is best soaked up by the bar’s small snacks, such as the well-executed charcuterie boards or the Jazzy fried chicken bits with spicy apricot jam dipping sauce.

Enjoy a bourbon and an unparalleled setting for dancing the night away. People frequently come across this tavern by chance, but it quickly becomes their favorite hangout.

Tipsy Rooster Liquor Store & Bar

rooster bar key west

 

The Tipsy Rooster Liquor Store & Bar is a 2022 Traveler’s Choice Award winner. It is a lovely little booze store and pub. Grab a drink at the bar, then, on your way out, swing by the liquor shop to pick up some reserves to enjoy later.

If you’re looking for a laid-back open-air tavern, check out the Tipsy Rooster. They serve delectable artisan drinks, like a zesty Key Lime Pie Pina Colada. The house-infused liquors in the bar are fantastic! 

Choose a beer or rum and order one of their wonderful pizzas. If you happen to be walking by the Tipsy Rooster, stop in for a drink—there’s even live music.

Favorite menu item: Pina coladas – their pina coladas are always a special mention by most patrons!

Smokin’ Tuna Saloon

smokin tuna key west
  • Location: 4 Charles Street, Duval St 200 Block, Key West, FL 33040
  • Price: $$ – $$$
  • Website: smokintunasaloon.com

 

The Smokin’ Tuna Saloon is located just off Duval Street and is a fantastic place to start or end the night with a cocktail. This establishment offers the feel of a beach bar but is still on Duval Street. For an open-air setting, this is one of the nicest bars in Key West. 

If you like fish, you’ll enjoy Smoking Tuna. Tuna Nachos, Tuna Melts, and the famous Florida Keys conch fritters are available. There are a couple of non-fish options for individuals who don’t like tuna. 

Smokin’ Tuna may not be exactly on the ocean, but its beach bar vibes are strong, thanks to an unpretentious atmosphere—the local-to-tourist ratio is a perfect 50/50—open-air environment, and a menu of over a dozen frozen cocktails, all delivered in a goofy souvenir cup. Head to the outdoor terrace for the ultimate experience; you’ll breathe in that fresh semi-tropical air and have the best seat in the house when the live music starts.

Favorite menu item: White Bean Chili – spicy white cannellini bean chili loaded with tuna and topped with sour cream

Garden of Eden

garden of eden key west

 

A nudist beach is well-known, but what about a nudist bar? The Garden of Eden is the most intriguing of Key West’s top bars! This “clothing optional” bar is on top of the Bull & Whistle. 

Tall jungle-link plants border the walls, making it impossible for passers-by on Duval Street to see inside. There is also a strong no-photography regulation in place. There will be no cameras or phones. A topless bartender (selling beverages that are slightly more expensive than elsewhere in town or even below) and a few dirty dancers are likely, but come on a bright afternoon, and you’ll discover nude sunbathers resting on lounge chairs. 

It is not really required to be naked here, and body paint is a fantastic way to be brave without revealing too much.

Hank’s Hair of the Dog Saloon

Sheldon Benton at Hank’s Hair of the Dog Saloon featured in TV Tim’s Key West TV

  • Location: 409 Caroline St, Naval Air Station Key West, FL 33040
  • Price: $$
  • Website: hankskeywest.com

 

Hank’s Hair of the Dog Saloon has great happy hours all day and live music. It is an excellent open-air bar that is almost embarrassing to be inside during Key West’s unending summer. 

They serve delicious meals in addition to wonderful drinks. Garbo’s Food Truck delivers some of the tastiest food in town to Hank’s clients. If you’re famished, try the umami burger.

Garbo’s has even appeared on Diners, Drive-Ins, and Dives. They have everything you need to nurse a hangover. Their burgers, hot dogs, tacos, and burritos are amazing.

Favorite menu item: Fish Tacos – fish of the day, red cabbage, mango, jalapeño, cilantro, onion, and housemade Caribbean sauce

Flying Monkeys

flying monkeys key west

 

Another well-known bar in Key West is Flying Monkey. Most Key West attractions on Duval Street are within walking distance of Flying Monkey. 

They’re famous for their frozen cocktails, which carry a serious punch. Their frozen cocktails are delicious since they are produced with just natural ingredients. 

Visit the Flying Monkey for a light lunch, supper, or cocktail. It’s a great place to unwind and one of the greatest patio bars in Key West.

Favorite menu item: Frozen drinks – The Banana Breeze and the Pain in the Ass are two of the most popular frozen drinks on Flying Monkey’s extensive menu.

The Original Jimmy Buffet’s Margaritaville

Eating at the Original Jimmy Buffett’s Margaritaville Restaurant in Key West, Florida by the altem life

 

Jimmy Buffet landed in Key West from Nashville in 1971. Many feel he discovered his natural voice as a singer in Key West. This was the first of Buffet’s Margaritaville bar restaurants in Key West. It’s one of the greatest bars on Duval Street and has been open since 1985. The bar is, of course, named after Buffet’s famous 1977 song, Margaritaville.

This isn’t the largest or even the greatest of Jimmy Buffett’s Margaritaville bar-restaurant complex, but it was the first, opening in 1985. Margaritaville Key West, located behind a pink facade in the commercial sector at 500 Duval St., offers a stage for musicians and the traditional tiki bar decor, as well as a full menu of eating and specialty drink selections.

For a fast bite, try some regionally inspired delicacies like conch fritters and a slice of tasty Key Lime Pie. Their unique beverages are available in either a regular 22 oz. glass or a souvenir blender cup. It’s worth a visit if you’re visiting Parrothead or want to soak up some wonderful vibes.

Favorite menu item: Cheeseburger in Paradise – loaded with mild cheddar cheese, applewood-smoked bacon, lettuce, and a tangy BBQ aioli

Hog’s Breath

hogs breath key west

 

Look for familiar faces at the Hog’s Breath Saloon. Kenney Chesney has been known to stop by with his guitar for a performance.

The Hog’s Breath offers a lively biker bar vibe. Live bands provide nice music, there are bikini contests, and there are plenty of good drinks. This is one of the nicest bars in town, with something going on all the time.

Despite its evident appeal to the Key West tourist trade, the low-slung and partly hidden Hog’s Breath Saloon is like a motorcycle bar; guests can dismount their Hogs and stroll up to a stool at the open-sided bar. It’s practically mandatory that guests leave wearing a Hog’s Breath T-shirt printed with the saloon’s renowned motto: “Hog’s Breath is Better Than No Breath at All.”

Favorite menu item: Whole Hog BBQ Nachos – tender slow braised pulled pork over house made tortilla chips, melted Cheddar and Monterrey Jack cheeses, chopped tomato, pickled jalapenos and a drizzle of tangy BBQ sauce. House salsa and sour cream on the side.

The Vibrant Nightlife At The Best Key West Bars

As the sun sets over the picturesque Key West skyline, the bars come alive with a diverse blend of music, laughter, and the clinking of glasses. Embrace the allure of the island’s nightlife, where every establishment tells a unique story and offers a different flavor of entertainment.

The vibrant nightlife at the best Key West bars beckons with promises of unforgettable evenings and an atmosphere pulsating with energy. So, for those seeking to infuse their vacation with a touch of excitement and the magic of the night, a visit to the best Key West bars is not just an option—it’s a must!

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Best Bars in Key West FAQs

Duval Street is the major thoroughfare of downtown Key West, extending north and south from the Gulf of Mexico to the Atlantic Ocean. It is one of the most popular locations on the island.

The street is the main bar strip in Key West, as it’s lined with multiple bars that offer a lively night out and signature drinks.

Because Key West is known for its wild nightlife, bar hopping on Duval Street after dusk is a natural hobby. Lower Duval is rowdier, with pubs and nightclubs like Sloppy Joe’s and Rick’s, but Upper Duval is more refined, with wine bars and cocktail lounges like Grand Vin and Point Five. The best Key West bars are a must-visit!

Rick’s Entertainment Complex is the 8-bars-in-one place in Key West. Every night of the week, you may have a completely different experience. Of course, there are calmer and more intimate locations (not to mention wilder ones) across Key West, but that’s not why you’re here. It’s ideal for a larger group, such as a guys’ weekend or a bachelorette party.

The nightlife in Key West is unlike any other. It’s a thriving and diversified environment that caters to various tastes and preferences. 

Key West is also known for its vibrant bar culture, which offers a diverse selection of options. The island is relaxed and welcoming, with a distinct blend of charm and excitement. The streets come alive with activity as the sun sets over the blue ocean.

Janelle
Author: Janelle

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