So you’re headed to Key West and trying to plan your Duval Street bar crawl? You’ve come to the right place!
As part of my recent “Great Florida Road Trip,” my partner and I participated in an ambitious bar crawl to eight of the most popular bars on Duval Street in Key West. I won’t lie, we were a bit overzealous with our plans, and I definitely paid for it the next day. That said, we had a blast visiting all the different bars and assessing the vibes of the various locations. So much so that while I was writing my Key West Itinerary blog post (which you should totally check out if you haven't already), I stumbled into ranking all of the bars we visited.
These rankings are based on our experience during a stormy Sunday night in January over MLK weekend. The most popular bars were crowded, but not packed. The crowd skewed 40+, although we spotted a few groups of college kids in the mix.
When creating these rankings, I mainly focused on the vibe; Was this a place I’d want to spend an hour or two? Was the music engaging? Was the décor interesting? Were the bartenders nice? I didn’t focus as much on the drinks themselves. Except for a few notable cocktails, I primarily stuck to vodka cranberries and my partner enjoyed margaritas and beer. We also simply didn’t have the time or capacity to take on every bar in the area, so I’m sure we missed a few popular gems (a few of which I named honorable mentions).
And with that, I give you…
EmmExplorer’s Best Key West Duval Street Bar Power Rankings (in Order)
Sloppy Joe’s – Perhaps the most famous in Key West, Sloppy Joe’s is a bit of a time capsule. With décor that pays homage to the island’s most famous resident (Ernest Hemingway) and one of the largest locations by square footage, this is an essential stop along any Duval Crawl. I had my favorite drink of the night here (Texas Lemonade), though we found the band a bit lackluster on a Sunday evening. That said, if we weren’t so ambitious with our bar crawl, I think I could’ve settled into a bar stool for a long while here.
Hog’s Breath – We kicked off our night here and it set a great tone for the evening. This indoor/outdoor establishment is secluded and gritty with great music and solid drink specials. I enjoyed my Key Lime Pie cocktail and my partner really dug the song selection from the solo guitarist. While there isn’t a “gimmick” to get you through the door here, this one sets a good tone and might be a good appetizer for your evening.
Garden of Eden – I’m embarrassed to have ranked this so high, but buckle in as I try to find the words to describe this place. This rooftop bar located on top of Bull and Whistle is the only fully nude bar in Key West. Yes, you read that right. And yes, it’s a real thing. Following our evening’s “turning point” at Irish Kevin’s (see below!) we bravely explored the garden (mind you, we stayed fully clothed the whole time). Honestly, it’s something you need to experience for yourself to believe. I’ll leave the details to the imagination but know it’s totally okay to go up there, have a drink, and not participate in the activities. Just brace yourself for some of the most interesting things you’ll ever see (and some things you’ll probably wish you could unsee). Don't worry, no photos are allowed.
Irish Kevin’s – Ah, the aforementioned turning point of the night occurred in the hallowed halls of this fine establishment. The drink to get here is a “Green Alligator,” but be warned, this gator bites! My parents mentioned this drink as a highlight of their Key West adventure but neglected to mention that they shared one gator between the two of them. Do yourself a favor and split this drink with a friend. Also, be warned, the combination of orange juice, blue curacao, and rum 151 is not an EmmExplorer favorite. But pull up a stool and enjoy a gator and some good ‘ole Irish tunes. This place serves as a great midpoint for your Duval crawl.
Captain Tony’s – This is where we ended the night, and it felt like the right place for a nightcap. This was the original location of Sloppy Joe's and remains a favorite of country star Kenny Chesney who is known to make surprise appearances from time to time. This dive gives off the essence of true Key West; dollars on the wall and the cheapest drinks you can find. Consider it a night caper, or maybe the start of your crawl as the intimate vibes are perfect for some good conversation.
A quite end to our night in Key West, Florida at Captain Tony's Durty Harry’s – We found our way here without a recommendation or reason to visit, but I’m so glad we did. The best music of the night was found in this dark corner behind Rick’s. Their band called The Durtbags was playing some rock hits and the crowd was very much into it. While I wouldn’t go out of your way to visit, it might be worth a stop if you’re looking for some solid music or planning your next move.
Enjoying some great rock hits at Durty Harry's in Key West, Florida Rick’s – We visited on an “off” night with rain, so our experience here was only so/so. The indoor bar downstairs was packed for an acoustic guitar performance, so we perused the upper floor which doubles as a dance club bumping the hottest hits of 2009 (and you know what, I’m here for it!). This seems like a place that could really go off during spring break or peak tourist season, so keep it on your radar.
A rainy night at Rick's in Key West, Florida The Bull & Whistle – While one of the oldest locations on Duval and frequently noted on “must see on Duval” lists, I was less than impressed with Bull and Whistle. Maybe it was our crabby bartender, the cigarette smoke getting blown in my face, or just the phase of the evening when we visited, but this bar struck me as being a bit rough and tumble compared to some of the other establishments on this list.
Key West's Best Bars: The Honorable Mentions
The Green Parrot – If the neon green lights don’t allure you enough, maybe the daily happy hour specials will. The Green Parrot makes nearly every “Best Bar in Key West” list, but we missed it as it’s located off of Duval and a little further away from the action.
The Rum Bar – As the name implies, this is a great stop for a vast rum menu and patio drinks outside. Like the Green Parrot, this one is a bit distanced from the hustle and bustle. We missed it last time, but have it on our list for future visits!
The Smallest Bar – This one makes for a good photo more than anything. This literal hole in the wall finds itself nestled into the middle of the Duval action and could be a fun spot to visit just to say you went there.
Wrapping It Up!
Well, my liver needs a vacation from this vacation. Despite the headache the next morning, we had a riot in Key West and have plans to return to more than one of these spots on our next trip. Which bar is most intriguing to you? Or is there a hidden gem that we missed that we should visit next time?
If you’re planning a trip to Florida, check out some of the linked blog posts below. I completed my “Great Florida Road Trip” and have plenty of tips and itineraries to share!
Until next time, keep on exploring!
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