Six Stops, Zero Regrets: Our Key West Bar Crawl Adventure

Our first bar stop in Key West was Captain Tony’s, which proudly claims to be the oldest bar in Florida—and honestly, I’m not arguing with them. The second you walk in, you know you’re somewhere with stories. The walls are covered in dollar bills, random memorabilia, and yep… plenty of bras. It’s a whole vibe.

There was a live band playing when we walked in, and they were good. The crowd felt like a perfect mix of locals hanging out and cruise passengers doing the same thing we were—trying to soak in as much Key West as possible.

Shoutout to Keith, the one bartender holding the place down. He was the only one working, but you’d never know it. He kept everyone happy and the drinks flowing.

If you go, definitely try the Pirate’s Punch. It’s delicious, a little dangerous, and it comes with a souvenir cup, which is always a win. Great first stop… and honestly, hard to beat. 

Our next stop was just a quick walk down the street at Sloppy Joe’s, whose slogan brags they’re “still the best party in town”—and honestly, the second you walk in, you get it. The place was packed, with almost no empty seats and a super lively vibe. A solo guitarist was on stage playing everything from Jimmy Buffett to Tom Petty, and everyone seemed to be singing along. 

Their menu features four exclusive cocktails, so of course I had to try one. I went with the Party Starter—not sure if it was the name or the ingredients that hooked me, but the mint in it was perfect on a hot day. Definitely worth going for if you pop in.

Sloppy Joe’s is loud, fun, a little chaotic, and exactly the kind of place you expect when a bar claims to be the best party in town.

Our third stop was basically right across the street at Pickles Pub, and they’re known for one thing you have to try: pickle shots. Yep… pickle shots. When in Key West, right? 

The place was pretty packed thanks to a college football game playing on all the TVs, and the crowd was definitely into it. A DJ squeezed in music during the commercial breaks, which somehow made the whole place feel like a sports bar and a party at the same time.

I actually loved the pickle shot—salty, tangy, and surprisingly refreshing. My husband… well, let’s just say he tolerated it and left the rest of the excitement to me.

Next up was Tiki House, and I’ve gotta say—this place was really cool. The whole bar is decorated top to bottom in full tiki vibes, with jellyfish lights hanging from the ceiling and dance music bumping in the background. It’s on the smaller side, but it still delivers a ton of energy without feeling overly crowded.

And listen… anytime I see a little fire symbol next to a drink, the moth in me has to try it. So of course I ordered the Zombie, which comes with a fiery flare at the end. Highly recommend giving it a go if you stop in—fun, strong, and totally on theme.

By this point we were definitely starting to feel the effects of our choices, so we wandered into Irish Kevin’s—you could hear the live music before we even made it through the door. This was probably one of the biggest bars we visited, and we figured grabbing some food might help us power through the rest of the crawl.

I ordered a Green Gator on a friend’s recommendation and added some Irish Spud Balls because… balance, right? We ended up staying here the longest because the performer was so good. He was incredibly versatile—singing everything from Eminem to The Cranberries with nothing but a guitar. I’m a total sucker for good live music, and he absolutely delivered.

There were TVs everywhere with the football game on, but he played right over it, which I personally appreciated as a non-football fan. Honestly, he was one of the best singers I’ve heard in a bar in a long time.

We even got a special visit from the owner himself—Irish Kevin—which just made the whole stop feel even more iconic.

And I have to mention this: their drink cups proudly say “I came… I drank… I don’t remember!”—and after a Green Gator or two, I fully understand why.

As for the drinks and food, maybe it was the drinking mood I was in, but everything had been a solid 10/10 so far, and the Green Gator definitely kept that streak going.

Our last and final stop (and I’ll let you guess why it was the last 😂) was Durty Harry’s, home of the world-famous Bloody Mary. They make them to order from scratch, and let me tell you—it did not disappoint. Both of us agreed it was hands-down the best Bloody Mary we’ve ever had.

The price was surprisingly great too. My drink and a bottle of water came to only $11, which felt like a small miracle in Key West.

You’ll know you’ve found the place when you spot the little house up in the tree—it’s their quirky, can’t-miss landmark and the perfect final stop before calling it a day and boarding back onto our ship.