Smallest Bar is the perfect name for this little establishment. What a great place for a drink while deciding on where to go next!

Ok, small review for small bar that made a small impression on me. I was told to go here and get a drink out of a pineapple. Who can resist that?! So we head there as soon as we start our crawl de Duval, and lo and behold, we find this tiny little awning with a barrel of pineapples and coconuts out in the front. Choose fruit. Give to guy with dreads. Guy with dreads puts a little rum in coconut and garnishes with a tiny piece of lime and umbrella. BF receives pineapple with rum and 2 umbrellas. We pay $29. Not drunk. Not even tipsy. I think he gave us one shot between the two of us. It was cool to check it out and walk down Duval drinking out of a coconut, but not a place I'll hit up again. read more

Should be called the nastiest bar in Key west. After ordering one beer and one mixed drink the bartender who should not be bartending a lemonade stand chargers me 16 dollars and that was the exact amount I had in cash left. Then he tells me I have to put some love in his tip jar. I told him that was my last dollar he replies do you think I'm working for free. And told me I should go somewhere else. Here is your tip a hole you should get a new job even if I had more cash on me I wouldn't give it to you. Save your money and go to local places while in key west this place is a pit with crappy bartenders. Try the Green Perot instead. read more

This place rocks! The bartender...don't remember his name, but he is a riot! We had so much a great time. read more

Smallest Bar - Dive Bars Near Me - Key West, Florida

The key lime pie shots were good. They young male bartender was super funny. He had jokes! Fun little place to pop in.

Had I remembered to write this review a week, month.. even a year ago then I would have given it 5 stars. Not because the drinks are so amazing but because of the wonderful memories that I've acquired here throughout the years. But today, things changed, I walked in with hubby in hand ready to grab a quick drink to cool us off. There was already a couple inside. They walked to the back of the bar (took two steps back) to give us some room to order. The lady behind the bar was really excited and friendly. She was older and very earth-y. She explained that she had invented this really wonderful fruity drink made of natural ingredients and promised that it would cool me down instantly and be 'the best thing I ever tried'. So I took a chance and ordered it. What I received... no, bought ($10)., was the worst concoction I have ever had the utter displeasure of tasting. It was bland, tasteless, mostly ice and water from my taste.. just plain bad. I felt too bad to tell her that to her face because she was an older woman who was so proud of the 'magical drink she made' so I sucked it up and thanked her before leaving. Beware the woman who tells you about a tropical drink she invented herself!!!! Other then that its cool to check out the bar because its so tiny. read more

The title says it all. It is a little larger than an elevator in the Hilton. The drinks are fine, the prices are touristy, and the bartenders are bartendery in the best way possible. Stop in for quick drink to say you did. No need to order anything fancy-just get the basic and check it off the list. read more

Fun little place to grab a quick drink while on Duval street. The concept is cool and it is fun to take a few pics of check-in on Yelp, but this is not a place to hang around as it is so small. However, it is a great tourist stop for anyone in Key West looking for an interesting picture and a decent drink. read more

The Smalllest Bar is small in stature and BIG on fun. I've been here several times, and each time I've been here I've had a blast. It really is tiny...only enough room for about six people to hang out at one time, but the atmosphere lends itself to a truly great time. You might walk in as a stranger, but when you leave you will have made friends with the folks that are there with you. In Key West, there are so many places to drink....but make sure to stop here while you are there. Nothing fancy... but you will be sure to have a good time when you are there. Cheers! read more

Let's call Smallest Bar what it is - essentially a roadside stand for drinks. And that's Kool & The Gang in and of itself, but if that road you're on the side of is the heart of Duval Street, Key West, you've chosen a particularly fine spot to set up shop. Sure, you can hang out inside, but lingering at the entryway feels almost like you're on your own front porch observing the humanity that's ebbing and flowing past you. Better yet, it isn't expensive. Smallest Bar is a key enabler of fun in Key West, and for its square footage, it packs a mighty whallop. read more

Bartender was really great and customers were even funnier. Perfect for grabbing a beer or two while doing the bar crawl down Duval. Prices are decent. read more

Soooo charming! Stop in for sure! Great drink, great bartender. Take pics!! You'll just pass by while taking a stroll down Duval. read more

One of the most interesting bars in Key West. Place is literally the size of a closet. About two stools but it's not a spot that draws a huge crowd for obvious reasons. Definitely worth checking out for a quick beer and shot. read more

Groovy little gem in the historic seaport district in Key West !! Had a drunk with my boyfriend on my birthday and had a nice experience. The bartender was very friendly and offered many lovely suggestions for the island ! read more

Worst experience i ever had in a bar. They had some guy in the side walk telling people to come in for fun n cheap drinks. So we went in and order two shots. 1.They where not cheap (20$) 2.The bartender dindt say it was a Cash Bar only. They didn't have signs saying this anywhere.... WE DID NOT DRINK SHOTS. We simply apologize n said that we dindt have cash. (n honestly not a lot of people carry cash anymore)...He went ballistic screaming at us saying how dare we don't have cash, that we weren't allowed to leave without paying (paying for something that we dindt drink) Swearing at us etc. Im opinion he was drunk. We just ran outta there scared..... read more

It is the smallest bar! Not a ton to say, the bartender was friendly and the service was quick. Good spot for a in and out shot. read more

Beer to go on the street is pretty damn cool, you can't resist going here on a saturday night Duval Crawl. totally a gimmick but it works, service was quick and friendly and we enjoyed it, read more

The rudest most unprofessional bartender ever. It is a walk up bar and as I walk up the bar tender told me I have to exit that I cannot have a dog. I said I appreciate that but he is my service dog and I just want a drink and we will walk away. He said the dog must stay outside. I made it clear about the service animal laws and also had an information card as well. He said no and that he was told by mngt under no circumstance does any animals at all aloud. I left two messages for the mngt wnd no call back I will report the business to the city of key west. It is a shame as businesses like this misrepresent key west and the beautiful and friendly place it is read more

It is what it is friends! The name says it all. Its like a guy with a cooler and a liquor license. P.S. the guy is like everyone else in KW... he's got a tip jar, use it or keep walking. P.S.S. again with the stupid parking question. THERE IS NO PARKING except for your drunk ass at the bar, or in a pink cab. DONT DRINK AND DRIVE! read more

The WORST most obnoxious bartender I have ever encountered!! My husband and I and our friends were walking by. My girl friend wanted to take my picture in front of the place while we waited for our husbands to catch up. We planned on having a drink. The bartender started yelling profanities at us about the picture and that we needed to buy a drink. Frankly, we were frightened by him. We never told our husbands how rude he was. We told our husbands he was closing up. JERK!!!!!! When we looked at the picture later, we see the bartender clearly flipping us off! read more

Smallest Bar - Dive Bars Near Me - Key West, Florida

Had a blast at this little place...for some reason I think this idea of a shoe box sized bar is awesome. I would think this place is definitely not for everyone, but my wife and I had a blast joking around with the bartender and random people. read more

It's a "Dip Bar"... Too small to be called a Dive Bar. Great use of space, really it's the skinny alley between two businesses. That's thinking outside the box. Love it. Fun way to make the business stand out. You have to get a drink just to say you did but make it after your 4th or 5th drink of the day.... otherwise you my not be so impressed with the taste or the price! read more

yes! the smallest bar, walk up do a shot or have a beer, shoot the shit with the bartender with something he has never heard before like how many people fit in here?! and leave. I think I asked if they had a mojito to go and he was like no.... read more

The smallest bar rules! Such a novelty that you must try and "so darn cute" according to my wife. I arrived and got a beer and stayed around to enjoy the atmosphere of being in the smallest bar. Great people to talk to as the 8 people that were inside rolled out into the street. A great time for sure! I find it funny that they have a restroom that is big. LOL read more

Extremely bad drinks and one very past and rude bartender. Tried to take a $7 tip for himself ( for $13) then tried to embarrass me in front of my wife. Poor bloke must be going through a messy divorce, haven't seen someone that confrontational ever. Oh and he started throwing ice cubes at us after we bought his crap drinks and we're taking a picture. Poor guy has zero life skills. read more

Unless you like to be disrespected and sleep in a dump I would not go here. I paid for a room in full online for one night with a zero balance. I was taking my son fishing and It was the only room available........ The night before I emailed asking questions about checkin. I got a response back so that was just one more confirmation they knew we were coming. The next day (day of arrival) our flight was delayed. I tried calling and...... no response. We got there at 9:00 that evening and the bartender said we did not have a room. I tried showing him the confirmation and email from management. He was beyond rude and said he didn't care and didn't have time to figure it out. (Working a 4' x 4' bar was too much for him). I told him I paid close to $300 for one night and to please figure it out. His response..... "Your in Key West, things cost." After 30 minutes of me not giving up, he finally gave us the "code" to the room. They ran another $65 cleaning fee on my card. That's TWO $65 cleaning fees I paid for one night and I highly doubt they even have anyone cleaning those rooms. I called a few days later after our trip and finally got a man Jarrett on the phone. He said he was refunding one of the $65 cleaning fees back. It has been two weeks and a refund has still not been issued. They will not answer emails or phone. To the bartender..... and management. Keep the money. You need it more than I do. There's no way in hell you'd survive working in a real bar or running a real establishment. Good Luck! read more

This should really be called "the smallest pours bar." Nice guy behind the bar but $10 for a one ounce pour of whiskey seems steep to me. I guess since only 2 or 3 people can be in the bar at the same time that the profit margin must be huge. read more

It's the worlds smallest bar all right! We stopped in here before our glass bottom boat ride and got a "panty peeler" as recommended by our friends who have vacationed in key west. It definitely boozed us up and we wish that we had stopped in AFTER our boat ride instead! Nevertheless, it was a fun experience and we'll definitely do it again when we go back!!! read more

Got drinks here a couple times and enjoyed both times. Tasty and you can get drinks inside a pineapple. Cash only, so make sure you have that. Also, the pineapple will cost you, $18 to be exact, which is a little bit on the ridiculous side, thus I cannot give it five stars. read more

I take one step in and all it takes is one step out to depart. This must be the smallest bar I have ever seen but its by far one of the loudest bars I have ever walked by and in. I did not have a drink here because the bar was packed (doesn't take much for that to happen). I can guarantee I will be having a drink there next time I visit Key West. read more

Awesome, in a very small way. Possibly the most fun bar I visited in Key West. read more

Smallest Bar - Dive Bars Near Me - Key West, Florida

I love it. I can always commend a place that uses all fruit in their drinks. Was damn god too. Kept my buzz going. lol read more

Smallest Bar - Dive Bars Near Me - Key West, Florida

Good Place to get hammered and people watch! it is so small there is nothing to review Make sure to take a photo of your pit stop. read more

I always go to this bar when in Key West, but I won't be going back after this trip. I stopped to ask when they would be opening and the bartender threw a beer at me (not joking). He told me to come back when it was open, but didn't elaborate on when that would be. He looked strung out so I'm assuming there is a substance abuse issue there. I chose not to stuff him in a trash can based on his haggard appearance. Save your money read more

I thought it was such a cute bar, so I was so excited to grab a drink inside but my excitements fell very short when our Bartender could care less that I didn't like my drink and wouldn't even engage with us in conversation. I normally don't mind that but when it's just the bartender and only two seats it's awkward. I'd say go check it out for a photo op but maybe skip the drinks unless your getting a beer. read more

This place is pretty great, can the bartender make the best rum runners in Key West. Make sure you stop by have a drink. Duval Street at its best! Ken is a great bartender make sure he's around mixing up the rum runners! Everybody read more

Smallest Bar - Dive Bars Near Me - Key West, Florida

While vacationing in Key West we stumbled upon this absolute GEM of a bar. The second we walked in we were greeted by John the bartender . John is one of the funniest people I have ever met in my entire life. My girlfriend and I sat for three hours making new friends left and right, laughing hysterically as John made fun of the people passing by. Imagine Dicks Last resort but 1000x smaller and 1000x more offensive . I LOVE IT. We actually sat and read the one star reviews TO JOHN and we all were in tears. If you're on vacation, loosen up a little and take a joke people!!! read more

Friendly bartender quick service if you can get to the bar! Because it is so small... Definitely a "I went to the smallest bar in Key West stop" I suggest staying away from the mixed drinks they seem incredibly weak, but the beer is beer and it is cold. read more

Small bar with a big heart. The owners son was an incredible bartender. Go in for good times and great conversation.

I can't emphasize enough how much this bar is a PIT STOP. I recommend going and doing a shot, they heavy pour. Great service.