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 ...