Some may remember “Awful Arthur’s” on Angela Street, just off of Duval. Well, after several tries over the past several years, the now defunct “Arthurs” has become just a faint memory. We’ve heard said, “all things happen for a reason”. So I have to assume Cowboy Bill’s was the reason here; a different, but refreshing, new saloon for the ever diverse Key West drinking crowd.

Cowboy Bill’s originally opened in a small narrow sliver of real estate on Duval Street next to Willie-T’s, but with only a beer and wine license, had a hard time drawing a western saloon crowd. Remember the movies, John Wayne swaggers up to the bar and snaps, “whiskey, and leave the bottle”. Well that couldn’t happen at Cowboy Bill’s until he moved into his new saloon, that included a full liquor license.

The “new” Cowboy Bill’s Saloon is actually a food, drink & entertainment complex. At the Angela Street entrance is an open air restaurant/bar. The menu is rather good for a bar with a variety of appetizers, sandwiches and entrees, including my favorites the “Cowboy Rib Eye Steak” and an excellent, falling off the bone, “BBQ Rack of Ribs”.  There are also several tasty seafood selections and a menu section for the little cowboys & cowgirls.

One might believe that that’s all there is, but move past the restaurant area and you’ll find the “Saloon”, which is actually two separate bars.  You’ll first run into the non-smoking, air conditioned sports bar with pool tables, electronic games and lots of TVs. It’s a great place to watch sports on TV, but last time I checked they didn’t have the “DirecTV NFL Ticket”, which is a bummer for those out-of-town visitors (or relocated locals) looking to root for their home team. But the place should draw a really good “March Madness” crowd during spring break.

If you prefer an outside atmosphere, smoking, cowboys & cowgirls, loud country music and live entertainment, the back bar is for you. It’s hard to find, but there is a small hidden entrance on Duval Street; just keep your ears open for the music. With live entertainment, a covered dance floor and a mechanical bull, you can’t help but enjoy this place. Yes… you read that right! A bull you can ride… no bullshit! I’m going to go out on a limb and say this is the only mechanical bull in the Florida Keys. And if you don’t enjoy anything else at Cowboy Bill’s, I guarantee that you’ll laugh your ass off watching some of the knuckleheads that try to ride that bull!

I must say I’m very impressed with the venue. You’ll find a unique blend of locals and tourists, the staff and bartenders are attentive, friendly, a bit sassy and always smiling, the food is good and the drink prices are quite reasonable. And like most bars in Key West, there are specials and happy hour prices. The back bar stays open until 4AM and serves food late into the night. I recommend it; especially when the bartenders get on top of the bar!

4 Responses to “Cowboy Bill’s Saloon”

  1. We were having a good time until we met the DJ. He was VERY rude! There were 2 men up there when I went to request 2 songs & wasn’t sure who the DJ was so I was basically talking to both men. He asked me “why are you talking to him, I’m the DJ”, So we started off w/ a bang. Then the songs I requested, I was told the owner hates the song & is forbid to play, ok how about “electric slide”, No, it’s not a country song! hmm. First time I’ve ever heard of that. And as I worked at Dallas Bull, one of the biggest country bars in Florida & they play it all the time. I told the DJ I’d like to speak to the owner & he said “whatever”. I told him he needed to treat the customers a little nicer. All of our family & many friends come there several times a year. We were told by A niece & nephew & their husband & wife to check out your place. I’ll have to guess right now until I talk to them that they didn’t have to talk to the DJ. Our bartender was GREAT!

  2. As a local I am now addicted to Cowboy Bill’s! This month they have brought in a new dj that is super high energy and really funny. Just 1 more reason I enjoy spending my hard earned $ there! Many Key West bars have staff that are grumpy or jaded…this place has one of the most energetic and attentive staffs. It is really refreshing. Many of my Conch friends say that this place reminds them of how Key West used to be – a place where everyone is welcome and you can have a great time without hassles. Great live music, cheap drink prices, plus it’s an indoor/outdoor bar! Sorry you had the run in with the (former) dj.

  3. I have to second the motion. Cowboy Bill has done a great job with the place. Had an absolutely fantastic Thanksgiving buffet and live music has been scheduled Wednesdays through Saturdays on a regular weekly basis. I stop by several nights a week!

  4. I recently went to cowboy bills on tuesday night. I love the fact that they have line dancing. the dj was great. high energy, great personality and also teaches dancing. i will be there every tuesday night for now on.