The Ultimate Key West Bar Crawl Guide (15+ Bars!)

There are no shortage of bar crawl guides when it comes to Key West. One of the islands favorite pastimes is to settle in at a bar, have a few cocktails and make some new friends. There are over 40 bars on Duval Street alone and yet some of the most unique and special places are off the beaten path and unexpectedly hiding on a quiet side street. Follow our Ultimate Key West Bar Crawl Guide and you will get to sample all of the bigger “must do” staple bars as well as be introduced to some of the lesser known spots visited mostly by the locals. If you check all 15 of our carefully chosen bars off of this list, you will be well versed and accomplished on your Key West bar experience. The bars are listed by geographical order, starting at the quieter south side of the island (towards the Southernmost Buoy) and the list works it’s way north towards the bustling Mallory Square side of the island. Other than south to north, they are in no particular order. They are all worth seeing and each bar offers something unique, sometimes historical and sometimes outright weird..

1. The Green Parrot

The Green Parrot Bar Key West, The Ultimate Key West Bar Crawl Guide

The Green Parrot, Key West

The Green Parrot is one of the most traditional “Old Key West” styled bars. At this unassuming and no pretense watering hole, you will find a healthy mix of locals sharing the bar with tourists in the know. Starting out as a grocery store with late night jam sessions in the back room in the 1890’s, the building itself has seemed to attract musicians since the day it was built. During World War 2, the grocery store was transformed into the Brown Derby Bar and served the Navy sailors stationed on the Key West Navy base. In the 1970’s it was transformed again into The Green Parrot and stayed pretty much the same as it is today. With a full open parachute hanging from the ceiling over the bar and a wild mix of eclectic art on the walls (make sure to look for “Smirk” a Key West famous painting done by artist Saul Paul in 1975), this bar truly creates a laid back atmosphere during the day.. The nights on the other hand are all about music. The Green Parrot has always been known to bring in some truly talented musicians – not your run of the mill cover artists. One of the best times to visit is during sound check, its not rare for people to be spilling out into the streets.

Locals tip – order a “Root Beer Barrel”, their signature but rarely advertised drink. Composed of a shot of root beer schnapps dropped into a rocks glass and topped off with tap beer, it is extremely easy to drink and tastes just like the soda. In our opinion, one of the best drinks on the island.

Green Parrot Bar, 601 Whitehead St, Key West, FL 33040. (305) 294-6133

2. Bearded Lady

Key West Ultimate Bar Crawl Key West

The Bearded Lady, Key West

One of the newer bars in comparison to the 1800’s Hemingway touting establishments, The Bearded Lady truly sets itself apart by being an oasis from the cacophony of down town Duval Street. Their slogan is “Good Beer, Decent Wine and Questionable Staff” and they live up to most of it (the wine is much better than just “decent”).  This dog friendly bar is a quieter place, you won’t find live music or thousands of dollar bills stapled to the walls. What you will find is an award winning selection of 16 ever changing, hand picked ice cold taps and over 25 different beers and seltzers to choose from. The wine selection is carefully chosen as well – in addition to a great selection of sake and a few malt shots to round off the menu. Don’t get the wrong idea by the sign that loudly announces “Sorry, We Are Open” – The Bearded Lady is a friendly (and very sarcastic) place. Visited mostly by locals (who are always happily willing to share their knowledge of Key West), tourists and other visitors are quickly learning that if you want to escape the heat for a while and enjoy some ice cold air conditioning and beer, maybe grab a handful from the candy bowl and get a selfie with a Betty White cut out – the The Bearded Lady is the place to go. It also doesn’t hurt that they have the cleanest bathroom on the island. As for the “Questionable Staff” – well, you are just going to have to find out about that on your own.

Locals tip – Order the “Angry Larry” – a pint of Narragansett, a shot of sake and a pretzel stick.

Bearded Lady Key West, 417 Southard Street, Key West, FL 33040 (305) 741-7167

3. Mary Ellen’s

Mary Ellens Bar Key West Ultimate Bar Crawl

Mary Ellen’s Bar, Key West

Tucked away on a side street where you are very capable of missing it, is another one of Key West’s newer bars. Walking into Mary Ellen’s you may not know what to expect. It’s dark, the temperature is very cold (most likely the coldest bar on this list), there are Christmas lights all over the ceiling, and there is a collection of quirky items all over the decor. Most noticeable is a legendary massive collection of vintage, modern and antique beer cans framed and adorning an entire wall. There is a small stage and a huge wrap around bar. Most likely after taking in all the visuals, you will notice the vibe. Mary Ellen’s almost always has something fun going on. Who knows what you are going to walk in to – a current sports game, a drunk spelling bee, trivia night, name that tune, a DJ spinning or a live band, Mary’s always keeps it interesting. Make sure to check out their website or Instagram for their current schedule – but if you can make a point of getting there for a Thursday night, be sure to book a seat for their Charity Vibrator Races – reservations are important for this event. The vibrator races are a high energy (and tons of laughs) night filled with great music and people donating to a good cause. It is one of the most unique things to do in Key West and you will be helping out someone in need. Mary Ellen’s also has an amazing menu with some very unique takes on bar style food. Order a grilled cheese sandwich and a bowl of grandma’s tomato soup, it’s amazing. Bonus –  the kitchen stays open pretty late.

Locals tip – Order a frozen Irish coffee and you get to pick your toppings (think childhood cereals).

Mary Ellen’s Bar & Restaurant, 420 Appelrouth Lane, Key West, FL 33040 (305) 294-7750

4. Willie T’s

Willie T's Key West Ultimate Bar Crawl

Willie T’s, Key West

When you think of a bar in Key West, what comes to most peoples minds are an open air atmosphere, a musician playing Tom Petty or some Buffettesque song on an acoustic guitar and dollar bills stapled to the walls. Well, this is the place in your minds eye. Willie T’s has an extremely laid back vibe with all an all outdoor seating and bar. They have live, crowd interacting music every day from 11am – 1:30am, and they bring in some solid acts. Their slogan is “You can’t drink all day if you don’t start in the morning” – and they live up to it. With 30 varieties of mojitos alone, they exist to serve. If you get hungry, Willie T’s also has a full menu of island style food – the conch chowder and and semolina gnocchi cakes really stand out. So grab a mojito or margarita, a dollar bill and a stapler and enjoy this quintessential Key West bar. T-Shirts are sold on location as well – never online – so you have to have been there to get one (kind of a badge of honor).

Local’s tip – Willie’s has daily 2/$12 specials.. the drinks change daily but the price stays the same.

Willie T’s, 525 Duval St, Key West, FL 33040 (305) 294-7674

5. Halo Rooftop Lounge

Halo Rooftop Lounge Key West Ultimate Bar Crawl

Halo Rooftop Lounge, Key West

Get off of street level for a bit and have a swanky cocktail at the Halo Rooftop Lounge. Lively, spirited and perched directly above Duval Street, this is the perfect place to ditch the crowds and do some people watching. Halo is part of and located within the Saint Hotel, you will have to enter hotel grounds and go up the large staircase. Take a seat on one of the railing stools and take in the sights. Although it is a smaller venue, there is still plenty of room for dancing to the live music that they offer. Halo is open 7 day from 6pm-11pm and has live music every night that starts at 8pm.

Local’s tip – Get there after sundown and experience dramatic electric blue accent lighting (also the best time to people watch).

Halo Rooftop Lounge, 322 Duval Street, Key West, FL 33040 (305) 294-3200

6. The Bull and Whistle Bar

The Bull And Whistle Bar Key West Ultimate Bar Crawl

The Bull And Whistle Bar, Key West

The Bull and Whistle Bar is actually 3 bars in one large complex. The 3 floors consist of The Bull on the 1st floor, The Whistle Bar on the 2nd floor and the Garden Of Eden on the 3rd floor. Each bar is fairly unique to each other and they are all well worth stopping in for a drink. The Bull is one of the last few open air bars in Key West. Featuring a stage for live music, a huge bar and plenty of seating. The large window and adjacent tables make for a great spot to sit and watch the people go by on street level. It is a low key, no pretense atmosphere and a must do on every Key West visit. Make sure to check out the art on the back walls depicting some of the history of Key West.

The Whistle Bar is one flight up. Think local dive bar feel. Pool tables, darts and other games. Clearly attracting a local party crowd, this bar is cash only but there is an ATM on site.  Where the Whistle Bar really shines is its wrap around porch. Stretching the length of the property from Caroline street all the way around Duval street, this is where you want to be to late night people watch.

Had a drink on the 1st and 2nd floors and ready to take it up another level? The Garden of Eden on the 3rd floor is clothing optional. During the day you will likely find people stretched out on lounge chairs getting rid of their tan lines. At night there is likely a DJ spinning and a good crowd of people dancing and having fun. If you are shy, don’t worry – wearing clothes is perfectly acceptable and it is a very respectful and mixed crowd of people. Just make sure to remember that cell phones are not allowed here. It is a great spot to sight see as well (the island) as it offers you a birds eye view of Key West.

Locals tip – They have 2 for 1 priced well drinks every day until 9pm.

The Bull & Whistle Bar, 224 Duval St, Key West, FL 33040 (305) 296-4545

7. General Horseplay

General Horseplay Key West Ultimate Bar Crawl

General Horseplay, Key West

Ready for a proper cocktail? Step into General Horseplay and find a seat at the bar. The atmosphere is as diverse with ingredients as their drinks. Dark, cool, mysterious yet quirky and a bit sexy. This speakeasy feel bar is where you will find proper drinks served in the proper glass, mixed by seriously trained bartenders. Absinthe, Smoked Old Fashioned, Mocha Espresso Martini with Cupcake Sushi to name a few. Watching the bartenders craft their drinks here is a show upon itself. When you are ready to be loud again – head to the back bar. With a fair sized stage, open air and stadium seating, General Horseplay basically has their own mini concert venue. Check their social media for the current line up, they rarely let a night go by without an amazing event taking place.

Locals tip – Join them for happy hour and roll a single dice to determine the cost of your drink.

General Horseplay, 423 Caroline St, Key West, FL 33040 (305) 741-7599

8. Hanks Hair Of The Dog Saloon

Hanks Hair Of The Dog Saloon Key West Ultimate Bar Crawl

Hanks Hair Of The Dog Saloon

Hanks Hair Of The Dog Saloon has a drink concession right at the entrance to the open air music venue – because sometimes the music is so good you don’t want to miss a beat going to the inside bar (not bad for roadies on the way out either). The front of “Hanks” is a spacious venue that hosts roughly 93 of the top local and touring musicians every month. It is also one of the few places that will let you reserve a table if your favorite musician is in town. Heading inside to the middle bar, you will find out why they have a reputation for some of the friendliest bartenders on the island. Not to forget some of the friendliest customers on the island – Hanks is a dog themed and dog friendly establishment. Buy some of their merch and they will donate a portion to pups in need. Hanks has a full liquor bar in addition to keeping over 20 local and craft beers on hand. If you wander outside the back, you will find an open air bar and Garbo’s Grill. Garbo’s itself is a hidden gem as an unrivaled gourmet food truck. Serving up items like Umami Sliders, Kogi Hot Dog and Korean BBQ Short Ribs, you can definitely expect far more than your average food truck.

Locals tip – Get your “Hair Of The Dog” 11am-1pm. Bloody Marys and Mimosas are 50% off.

Hanks Hair Of The Dog Saloon, 409 Caroline Street, Key West, FL 33040 (305) 509-7758

9. Smoking Tuna Saloon

Smokin Tuna Saloon Key West Ultimate Bar Crawl

Smokin Tuna Saloon, Key West

The Smokin Tuna Saloon is a funky, off the beaten path bar that tourists find to be a hidden gem and to locals – its a staple. The “Tuna” is a half indoor and half outdoor back alley saloon setting with 2 large bars, a large stage and plenty of seating. They offer a full menu and get rave reviews on items like their tuna tacos and their smokin tuna dip. Where they excel though is the musical atmosphere. With a raised, courtyard stage and plenty of room to dance, the Tuna fills their schedule with 2-3 live music acts per day, every day. Starting at 1pm, 7 days per week, the Tuna will entertain you with some of the best rock and county musicians in Key West. Always a casual atmosphere, sometimes rowdy (in a great way) there are always memories made at the Smokin Tuna. Settle in for a cold one (take home a logo’d plastic cup) and enjoy singing along to one of your favorite songs.

Locals tip – If you want to buy some souvenir merch and don’t want to carry it around with you, they will ship it for free ($50 minimum).

Smokin Tuna Saloon, 4 Charles Street, Key West, FL 33040 (305) 517-6350

10. Tree Bar

Tree Bar Key West Ultimate Bar Crawl

Tree Bar, Key West

Part of the Rick’s & Durty Harry’s complex of 8 bars on Duval Street, The Tree Bar is definitely the most intimate. The Tree Bar is very had to miss if you aren’t familiar with it. There is a large Monkey Pistol tree outside of 202 Duval Street – and sitting under the shade of that tree are a mixture of locals and tourists alike. Pull up a stool and watch the people and cars head down Duval, order up a cocktail where the bartenders fresh squeeze the juice for your drink and relax while the tree blocks the sun. One of the most unique aspects of this bar (besides the huge tree) is that it is quiet enough to hold a conversation, yet you are in the middle of all the action of the 200 block of Duval Street. You can make new friends or catch up with old ones and still enjoy the music that just seems to seep out of every corner of Key West. If you are looking for more action, you are right at the entrance to the other 7 bars of the Rick’s & Durty Harry’s complex – something for everyone.

Locals tip – Many people say that the Tree Bar has the best bloody Mary on the island.

The Tree Bar, 202 Duval Street, Key West, FL 33040 (305) 296-4890

11. Sloppy Joe’s

Sloppy Joes Bar Key West Ultimate Bar Crawl

Sloppy Joe’s, Key West

This 1933 prohibition era Key West staple is arguably the most famous bar on the island – but there is no argument that it is absolutely a Key West icon. Pretty much anyone that has been to Key West knows the name Sloppy Joe’s, and for good reason. “Sloppy’s” has live music daily and hosts an array of events for every imaginable reason. From hosting the Hemingway look alike contest, dropping a conch shell on New Years Eve, sponsoring the power boat races or throwing a flapper costume party celebrating the end of prohibition – there is always something happening here. There is also a surprising amount of history just (literally) hanging around the bar. The tip bell at the main bar is from a Coast Guard cutter boat, Hemingway’s skis are hanging on the wall, the propeller hanging from the ceiling is from one of the first Pan AM Flights from Key West to Havana, the framed bat on the wall? It was used to “keep the bar in line” during the 1930’s and 40’s.

Locals tip – Head to the back bar (turn left at the restrooms) Joe’s Tap Room. Try the Joe’s sampler – 5 for $7.75 3oz craft beers of your choice.

Sloppy Joe’s, 201 Duval St, Key West, FL 33040 (305) 294-5717

12. Irish Kevin’s

Irish Kevins Bar Key West

Irish Kevin’s, Key West

Another Key West Institution, this time in the form of an Irish pub. Their motto is – “I came, I drank, I don’t remember” and if you happen to stay a while at “Kevin’s” you will know why. This is the type of bar that has entertainment from open to close 7 days a week, and the entertainers are partly musical, partly comedy and all fun. You may be called into the bar from the street, brought up on stage, or have a shot poured into your mouth on the dance floor. Weather you take place in the pint drinking contest or not, the entire crowd is involved in the fun at Irish Kevin’s. If you are lucky, you may catch Kevin himself take the stage. With a full bar, traditional food menu, live music, air conditioning and a great crowd – it is a hard bar to leave once you have joined the crowd. Don’t forget to check out the Jameson bottle chandelier hanging from the ceiling.

Locals tip – 4:30-5:30 daily -$5 Burgers, well drinks and Kevin’s pints.

Irish Kevin’s Bar, 211 Duval Street, Key West, FL 33040 (305) 292-1262

13. Capt Tonys

Capt. Tony's Saloon Key West Ultimate Bar Crawl

Capt. Tony’s Saloon, Key West

Having a drink at Captain Tony’s is basically a rite of passage in Key West. The patrons are as diverse as the building’s history. Capt. Tony’s may just be the Holy Grail of dive bars. Frequented in the past by artists and celebrities such as Hemingway, Capote, Tennessee Williams and Jimmy Buffet, “Tony’s” still brings in A-List patrons on a regular basis. The bar stools are named after the famous who have paid a visit and it is a sight to see exactly how may people have visited this Key West landmark. It is rumored that Buffet got his start here and he also immortalized Captain Tony’s Saloon in the first line of his song Mango In Paris. In addition to Parrot Heads, this bar is also a favorite among fans of the paranormal. In 1852, the building was an ice house and doubled as the city morgue. There is also a tree growing through the middle of the bar and the roof of the building. This tree was the “hanging tree” and it is rumored that 17 people were put to death from it’s branches. In the 1930’s, “Tony’s” was also the original location of Sloppy Joe’s before a rent dispute forced them to move into their current location. Captain Tony’s has live music daily and be sure to bring a few quarters. There is a large Jewfish mounted above the sign outside. It is tradition to stand backwards and throw a quarter into the Jewfish’s mouth. If you get it in, local lore says you win a streak of good luck for your entire time on the island.

Locals tip – 22oz Capt. Tony’s Amber comes served in a free souvenir cup to take home with you.

Capt. Tony’s Saloon, 428 Greene Street, Key West, FL 33040 (305) 294-1838

14. Tiki House

Tiki House Key West Ultimate Bar Crawl

Tiki House, Key West

Right next door to Capt. Tony’s is one of the most fun and whimsical bars in Key West. The Tiki House sports a retro Polynesian decor, unique and interesting (and potent) drinks served in an array of funky glasses, tropical movie and TV clips playing in the background and live music in the evening. The bartenders are friendly and always offering to educate their patrons on the captivation drinks they are serving. In fact, you can even sign up for a Tiki class and learn how to make them yourself (Wednesday and Saturday, 1-3pm). Their signature drink is the Key Lime Colada with a graham cracker rim – a cocktail not to be missed. . but if coladas are not your thing, try one of their Mules mixed with homemade ginger beer.

Locals tip – Zombies are 2 for 1 during happy hour. They are fire, most literally.

Tiki House, 430 Greene Street, Key West, FL 33040

15. Shots & Giggles

Shots and Giggles Key West Ultimate Bar Crawl

Shots & Giggles, Key West

Many travelers to Key West ask “Where do the locals go?”. If you asked that question, Shots & Giggles is the answer. Shots & Giggles is the kind of place that you immediately feel like a regular, even on your first visit. Very slightly off the beaten path of Duval Street, “Shots” is a bar inside a classic Key West conch house, and it feels like home. Air conditioned, dog friendly (even encouraged), major sporting events on TV, owners on site to greet patrons, a front porch to sit out on and reflect on your day, and complete with a courtyard with picnic tables – it is very easy and enjoyable to lose track of time here. The drinks are well crafted, cold and cheap. The wine selection is amazing and they have over 60 craft beers and seltzers in house. There is even a walk up window for drinks in the courtyard or to go. Although mostly filled with friendly locals, tourists are very much encouraged to stop in for a drink and stay a while.

Locals tip – There is an ever changing drink deal at Shots & Giggles daily, such as Mermaid Mondays $5 margaritas, Tuesday & Thursday 2 for 1 Deep Eddy’s, Whiskey Wednesday $5 select whiskeys, Tequila Fridays, Bombora Saturdays PLUS a daily 20% off happy hour!

Shots & Giggles – 201 Ann Street, Key West, FL 33040 (305) 304-8562

 

 

If a self guided tour is not your thing, there are also two companies that offer professionally guided tours:

Key West Food Tours offers a 3 hour Cocktail Crawl, $79 per person. The Cocktail Crawl includes 5 local cocktails and 2 generous food tastings from some of the best bars in Key West. 21+, Rain or Shine. You Can Book Your Tickets HERE.

Or, of the more macabre, check out the Bone Island Haunted Pub Crawl. For $24.95 the Haunted Pub Crawl runs every night at 8:30pm and is a 2 hour long guided tour and spooky account of Key West’s most haunted bars. Includes a souvenir T-shirt. You Can Book Your Tickets HERE.

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