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Tipsy Rooster Liquor Store & Bar
#1 of 61 Nightlife in Key West
I love this little bar! Situated right next to the Southwinds Motel (which is also fabulous), this was the perfect spot to stop for a quick drink on our way out, and is also just steps away from the main pool deck...
We bellied up to the cozy and clean bar and there we met Robbie!! Robbie served us beautifully made drinks with a big smile and sparkling personality.
The Green Room
#2 of 61 Nightlife in Key West
Bonus points for the owner also being the owner of one of our favorite nightlife spots at home! Casual atmosphere in the heart of everything.
We stopped by the Green Room when we heard amazing live music from Duval Street- "Pops" made our anniversary with great conversation, awesome drinks and good laughs- our new favorite bar on Key West and we have lo...
Greene Street Cigar Company
#3 of 61 Nightlife in Key West
Well yes I love cigars and wine and beer and yes this comfortable little pub is first rate !! Cozy leather sofas, spacious bar seating, great a/c, amazing air filtration, and the Best happy hour on the island.
Katie, the bar tender, was knowledgable and super friendly!!
Key West Pub Crawl Tour
#4 of 61 Nightlife in Key West
We definitely would recommend doing this if you like nightlife and enjoying cocktails!
We were all so happy we did this the value was great and we really got to learn some cool things see bars all with great service and had wonderful cocktails (feeling very good by the end) Beau was our guide and he...
2 Ways to experience it
The Rum Bar
#5 of 61 Nightlife in Key West
There are many nightlife and drinking options in Key West, but we liked this one in particular.
A rum bar as you would picture it in your dreams: - Great selection of rums - A good choice of your favorite rum cocktails - Barmen who know their business and can tell you all kind of stories about the rum - Very...
Sunset Pier
#6 of 61 Nightlife in Key West
great mojitos from street vendors or shoreline bars, plus art, musicians, jugglers and of course the legendary CatMan show! capped off by a spectacular sunset and view, you haven't experienced key west unless you'...
This bar is at the southernmost point of the continental United States, from here you can watch the most beautiful sunset over the bay, to a live band and a cocktail, fantastic!
3 Ways to experience it
Little Room Jazz Club
#7 of 61 Nightlife in Key West
Little Room Jazz Club was exactly what we were hoping to find - intimate, dark and romantic - it's an embracing escape from the craziness of Duval Street.
Jenn gave us excellent, personable service from wine bar.
Flying Monkeys
#8 of 61 Nightlife in Key West
Flying Monkeys has a great relaxed atmosphere with friendly bar staff and a great range of frozen cocktails including some well selected blends of 2 other cocktails.
The BEST bar with the BEST drinks and the BEST service.
Green Parrot Bar
#9 of 61 Nightlife in Key West
I guarantee it will be original, awe inspiring, mesmerizing, and soon you too will be a devotee of this Green Parrot, the best bar in the world.
Great Old Bar, Great Music, Great Times
Aqua Nightclub
#10 of 61 Nightlife in Key West
Faith was spot-on perfect with her Celine Dion and Cher segments, Jessica was amazing as Stevie Nicks and Inga was so outrageous and had the entire club roaring with laughter!  
In addition to the main show bar, Back Bar and Side Bar are also great, the former providing a little peace and quiet in a lovely outdoor setting, and the latter offering up an upscale, modern dance space.
801 Bourbon Bar
#11 of 61 Nightlife in Key West
Excellent place to hang out love the bartender Jessie is awesome Great bar and entertainment and fun fun fun
I had a great time at the 801 Bourbon Bar, Rachel the MC was awesome, funny and fun!
Capt. Tony's Saloon
#12 of 61 Nightlife in Key West
We were at this bar everyday on vacation, we could always get a seat, there is live music and the bartenders were super cool!! Oh the pirates punch, delicious and deadly lol can’t wait to go back!!!!
This is a MUST DO for anybody wanting to have a drink and a unique bar experience in one of the most historic bars in the U.S. Cheers Hem!
2 Ways to experience it
Vinos on Duval
#13 of 61 Nightlife in Key West
Lovely wine bar with great choice of wine and fizz by the glass
Hubby and I walked up the steps to this little wine bar and totally loved it!
Eat Drink Discover Key West
#14 of 61 Nightlife in Key West
Awesome tour of Key West bars and how rum is made.
From there, we crossed the street to Pacific Jewelry (not to be confused with the Diamonds International chain next store, which is ubiquitous in every cruise port), where we were shown a silver bar and coins reco...
2 Ways to experience it
Durty Harry's
#15 of 61 Nightlife in Key West
Awesome Bar, Awesome Band
Second visit to Key West and Durty Harry's has become one of our favorite bars.
Shots And Giggles
#16 of 61 Nightlife in Key West
We have been enjoying this bar for the last couple of years from our first visit they made us feel welcome it's a locals hangout but everyone from bartenders to the locals are great easy to talk to.
Short Walk but Big Difference From Duval St. Bars
Viv Wine Bistro
#17 of 61 Nightlife in Key West
This little wine bar on a side street couple blocks from the busy Duval, it will take you to the perfect mellow easy going vibe that you must need while you enjoying a glass of wine, location and staff make this p...
Everything from our wonderful bar tender Amanda, to the beautiful meat, cheese, and wine paring we did.
The Bull And Whistle Bar
#18 of 61 Nightlife in Key West
There are many places that you can stop in for a beverage and live music along Duval Street, and the Bull and Whiskey Bar needs to be on you list!
This is a fun bar that almost anyone who walks in can enjoy!
Smallest Bar
#19 of 61 Nightlife in Key West
Tommy is a phenomenal bar tender, funny conversationalist, and makes the BEST Rum Runner in and around Key West!
Fun bar to stop and get a shot of your favorite beverage while on Duval Street.
Garden of Eden
#20 of 61 Nightlife in Key West
Great fun at a clothing optional bar... Loved it!
We are in our fortys and found this rooftop clothing optional bar to be a blast .
Cork and Stogie
#21 of 61 Nightlife in Key West
Great little cigar lounge and bar with all types of beers.
Great craft beer, wine, and cigar bar with local feel.
BottleCap & Blue Room Key West
#22 of 61 Nightlife in Key West
great bar on the south side of town that rocks late in the night..ca couple different bars and you can purchase food too!
The bar tender and wait staff were very attentive and friendly.
Hard Rock Cafe
#23 of 61 Nightlife in Key West
2 Ways to experience it
Bourbon Street Pub
#24 of 61 Nightlife in Key West
We recently visited Key West and nightly visited Bourbon Street Pub and met an outstanding bartender Brad (mainly bartended the back bar) he made the experience fun and memorable with exemplary service!
Bourbon Street Pub was definitely a great stop on our tour of Key West Bars.
Tiki House
#25 of 61 Nightlife in Key West
What makes a good Tiki bar? Tiki-tacky decor, great bar tender, great prices (happy hour!) and of course a GREAT Tiki drink.
Fun atmosphere, good drinks and it's something a little different from the traditional Key West bars.
1 Way to experience it
Agave 308 Tequila Bar
#26 of 61 Nightlife in Key West
This is a pretty cool tequila bar, with a lot of margarita variations - jalapeño, strawberry, basil, ginger and more!
Nice tacos, very fresh, attentive young lady behind the bar, and well informed about the tequila offerings.
Tattoos & Scars Saloon
#27 of 61 Nightlife in Key West
Great Bar!! Fantastic service!
Clean bar, good beer and great service.
Kelly's Caribbean Bar, Grill and Brewery
#28 of 61 Nightlife in Key West
General Horseplay
#29 of 61 Nightlife in Key West
Debbie at the back bar is awesome!!! Super fun place, great drinks and awesome peeps so fun!!!
Whenever we go to Key West, it's always fun to go to the traditional Key West bars during the day and we save this little gem for the night.
Turtle Kraals
#30 of 61 Nightlife in Key West
Hopefully you get Nick and The view from bar is amazing!
The views of the marina are fantastic and they have a tower bar as well but it was so hot they were closing the upstairs for the day.