I recently returned from a "business trip" in Key West - I found myself walking into Cowboy Bill's many times during the week in between work functions. Â
The place had a great party vibe every night I was there. Â There was good music playing and people from all walks of life just having a good time, drinking and carrying on. Â Watching ladies attempt to ride the mechanical bull was hilarious! During the day, it was nice to just chill at the bar with some food and a beer to watch sports on the TVs. Â The bartenders and servers were beautiful and attentive, and the food was awesome - I highly recommend the Gumbo and Alligator Bites. Â
All in all, a cool place with a friendly party atmosphere. Â Next time you're in Key West definitely give Cowboy Bill's a try!
I arrived in Key West in the middle of Fantasy Fest... it was a bit of a shock.
So much nudity... so much body paint... so many people who look like my uncle trying to flirt with me...
This young lady from Aus was way out of her element! I'd just been to Miami and killed all my brain cells... I felt a million miles from home... and all I could think was "please leave me alone with a beer, some food, wifi for my iPad and a screen to watch the baseball..."
Cowboy Bills saved the day! Despite the fact that there were women in the front window having their boobs painted green ("darlin' that colour takes ten years off your chest"?!), this bar was the perfect place to chill out on my own and recalibrate... while watching the Giants, snacking on nachos and drinking cold American beers (is it any wonder I felt bloated after my holiday?).
The drinks were cold, the food was satisfying and the staff were incredibly friendly (I love American hospitality!)... It's not the kind of place I'd usually hang out in but it was perfect at the time.
I just wish I'd seen the mechanical bull in action...
Ok, I'm giving this 4 stars as a Sports Bar and nothing else. Â We were looking for a spot to watch the Seahawks kick some 49ers butt during Sunday Night Football. Â I Yelped Key West Sports Bars, but Cowboy Bill's didn't have many (or any?) reviews that addressed what it was like to watch a game.
We walked past this place several times, saw all of the TVs and decided to skip our initial destination (the Rum Barrel) to watch the game. Â At Cowboy Bill's we got our own TV in our booth and were able to watch the game easily, hear everything, and snack on food and beer for 3 hours. Â If you're not into sports, this place is HUGE and has soooo much other space for you to enjoy and not obstruct the view of sports fans trying to get their game on.
As bars go, this place is HUMONGOUS! Â It really is not my type of bar ordinarily (I'm somewhat of a foodie, and the food here -- Mexican -- is just ok), but to watch a game I'm sticking with Cowboy Bill's every time!
Service was very good, but the food was mediocre. We ordered cheese enchiladas that initially came without the cheese melted, but even after reheating, were rather tasteless, almost like the cheese was some artificial construct. The chalupa was more like a tostada. Good virgin pina colada. Its annoying to have a tv monitor right at the table. Atmosphere was like an upbeat bar restaurant. Vegetarian options are limited. We went here for Mexican food, but would not go back for that.
Review Source:I have always feel Duval St. in Key West feel just like NOLA Bourbon St. After I found and experienced Cowboy Bill this evening, my theory is completely validated. There is a bar in NOLA that is just like this one, down to the same mechanical bull, maybe, or the sibling of the bull.
If the bull isn't enough of entertainment for you already, good thing Cowboy Bill also have live band music pretty much always available. Beers and drinks here is pretty reasonable, but nothing extraordinary.
I think I read someone mentioned "Sexy Bull-Riding Night," well, let me tell you, there is NO SUCH THING as sexy mechanical bull riding. There are speedy dismount (unable to hold on) mechanical bull riding, and then there are ungraceful dismount mechanical bull riding. That's it. They're the universal experience of mechanical bull riding.
We heard live music from a block over and followed the sound to Cowboy Bills. It was a Monday just before the sunset & it was dead! The bartender was super
friendly and the music was awesome. I couldn't believe that there wasn't more people. We came back on Wednesday night and it was packed out!! Mostly dudes  waiting to see the sexy bull riding contest. If you want to see boobs & like hanging around a bunch of idiots then come here on Wednesday! If not, come another night.
Always a great time at Cowboy Billy's! Â Within the last few years Bill's has grown from nothing to a sprawling bar growing between the buildings and into them as space becomes available. It now houses several bars including a sports bar, a dance floor, a mechanical bull riding area, pool tables, and more. Â They used to have a dartboard, but have since removed it.
Bill's always has a crowd, but probably even more so on Wednesday's for the bull riding competition. Â Definitely check this place out, it is Key West's only country bar, but is really great for anyone. The live bands are always quality.
Look for the cowboy sitting at the entrance to a long alley and go right on in. I really enjoyed Cowboy Bill's, didn't have any problems with service and absolutely got up on that mechanical bull. No, not on "Sexy Bull-Riding Night", thankfully. Mr. H tried it out as well and I'm pretty sure we both lasted no longer than 5 seconds on it.
We went on two beautiful Key West nights and sat outside, drank buckets of PBR's and listened to great live music. It was late May, not too hot, and not too crowded.
I'd go back the next time we're in KW.
I gave 4 stars only because when I asked for a Malibu Bay breeze, the bar tender didn't know how to make it.
Other wise great place to sit and have a drink. Sports on the TV's, live entertainment in the front. Pool tables, beer pong towards the back and in the back live band also. Great entertainment, and can ride the bull.
If you want to listen to country music, watch a "sexy" bull-riding contest, and drink cold beer while sweating your ass off on a hot KW summer night, then this is the place for you. Â
For the young boys, (or old) you will see some boobs...not usually very nice ones, but still entertaining to see the girls and ladies try to be sexy while riding a mechanical bull. Â
The live band played decent music, there was some line dancing, the place was pretty packed, and there were a few cool places to get away (lots of rooms indoors as well, pool tables, etc...)
This place is HUGE, you would never think it from the outside. It has the main dining area, then another room to play pool, another room to eat, another room which a bar area, and then the outside patio, which also has seating. The outside area has a "riding bull" and a little stage for live music. The food, "tex-mex" was pretty good. A fun atmosphere overall.
Review Source:While in Key West, I really wanted to check out this place since I'm a big country music fan. Â So while on our tour there, my wife and I stopped by this place on a Wednesday afternoon. Â The place was dead and wasn't even playing country music. Â They were playing Kid Rock at the time and I'm sorry, but Kid Rock isn't really country music! Â I'm sure this place is a lot more fun at night, but unfortunately we couldn't experience it then. Â So, as far as I'm concerned, the southernmost bar that was playing country music while I was in Key West was Margaritaville, not this place!
Review Source:Well this place was interesting. Â My friend asked if we would be interested in 'sexy bull riding'. Â I thought about it on our way up there, but I was wearing a dress so thought it might be a bit too revealing up on a bull.
Well, turns out, sexy bull riding, you just take your clothes off, so it doesn't really matter what I'm wearing. Â This is just strange. Â But, it was packed and there was entertainment in every room (self-made) and I didn't have a bad time at all. Â There's 3 or 4 different areas inside depending on your night's desires and a huge outdoor area. Â Part of it is a stage, another part the bull pit and lots of surrounding area. Â Don't worry, if you're at the inside bar, you can still see boobs on the bull on their big screen TV's. Â
I probably wouldn't choose to hang out here frequently, but when in Key West...
Oh Bills. Where do I begin? Bills is a great place to start off your night. Its outside, the music is loud, and the cover bands are always good. The bartenders are fun, and nothing beats watching absolutely hammered chicks, trying to look sexy on that damn bull. It never works, they always look like fools, and to me, that is entertainment in its self!
Review Source:A fun place, this bar is very big with a spacious outdoor area. Also a mechanical bull which I rode for the first time in my life ($5). It's got some charming features like a bar stool that is a horse saddle and the saloon doors that are quintessential in any old west hangout. I was very happy to stumble upon this place. It looks like it can get pretty wild in here ( there was a lady wearing only bodypaint dancing) which it makes it all that much fun. There's also live music and beer pong inside, so you may find yourself inside here for a while drinking the night away.
Review Source:Another one of our "must stops" while in KW. If you go on a wed night (sexy bull riding, ladies drink free from 9-11..FREE!) get there super early to get a spot. They have very good prices and our waitress that wed night (Paula) was totally adorable and great at refilling my free beers. We like to go there at other times too for the friendly service, cheap prices and good music.
Review Source:There are certain, undeniable truths. Deep down inside, everyone except the deathly allergic finds kittens cute, no matter what protestations of cynophilia they make or how loudly (and the deathly allergic just end up internally conflicted). More relevant to Cowboy Bill's is the fact that all straight men enjoy breasts. We're not a bunch of slobbering Lotharios, and evolutionary desires towards lechery are typically tempered by everything from advanced education to socio-religious norms, but I am skeptical of anyone claiming transcendence of genetic programming.
That said, one can like the product despite disapproval of the process. Enter the 'Sexy Bull riding' contest, occurring on warmer Wednesdays at CB's. The hook, delivered by a 'Tombstone' lookalike outside the bar, is something along the lines of 'drunk sluts taking their tops off, in here!' and 'Tits, boys.' Crass, perhaps, but undeniably accurate.
Four separate bars ring a padded pit, providing a variety of vantage points over the mechanical bull. There's an indoor sports bar, pool tables and other drinking companion games, a stage, and a dance floor. Decor is debatable country western, but mostly just functional. The lower end of the bar food spectrum is served, paired with buckets of PBR, MGD, and the Anheuser Busch family. Mixed drinks, too.
But no one goes to a sexy bull riding contest for culinary exploration. They go for peer-pressured displays of light to moderate sexual exploitation. Maybe, if they're trying to dupe themselves into some elitist semblance of higher purpose, they say they go to watch the dueling genders engage in skirmishes of mutual manipulation. Who wins, the girl who gets free drinks or the guy who gets free tits?
Judging by the crowds, and despite the $250 prize to the eventual (and generally fully nude) winner, I'd say Cowboy Bill's comes out on top.
Also, though CB's is firmly planted on the rainbow end of Duval Street, I recommend that gentleman do not attempt to ride the bull in pursuit of the Sexy Bull riding prize. You will be thrown.
Fun place to watch wannabe cowboys fall on their butt when their ask for the hardest level when they have never ridden a mechanical bull in their life.
We came here for the bull riding competition that was scheduled to start at 11p but actually started at 1130p. I guess that's a good way to get more people to buy drinks. It seemed to work on my behalf.
If you are a beer drinker there is nothing special here, just the typical Bud, Miller and Corona.
Overall if you are in the Keys this place is still worth a shot to come and make fun of the people on the bull.
Cowboy Bill's, by far, got us the drunkest we've ever been as a collective group. I don't even know how it happened. One minute we're doing shots and taking pictures with the head-cutout-scene-thingy, and the next thing you know, we're blacked out and riding the bull and freaking out to country music  and smoking random cigarettes (according to the 10,000 pictures we took).
I can't tell you much, other than the fact that we had a great time and got totally out of control. Definitely go here.
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