
Photo by Cathy Salustri
Last month, Rick and I did an episode of the Florida Spectacular podcast about the best Florida dive bars. You can pop over to the show notes to see which ones we included — and I’m sure we missed some good ones, although good is maybe not the best term.
But that made me think about the Florida Keys. I know of one or two, but the Keys has a lot more tourist-centric bars than ones that I would call dive bars.
So I asked Brad Bertelli about Florida Keys dive bars, and sure enough, we came up with enough to have a whole separate episode about them on our Florida Keys Spectacular podcast. If you already support the podcast, you have access to that content. If you don’t, well, you’re missing out on a lot of fun facts and inside info on the Florida Keys. Not to worry, though — here’s the list of what Brad and I think are the best dive bars in the Florida Keys.

Photo by Cathy Salustri
Best Florida Keys Dive Bars
Note: Although most of these didn’t make Southern Living’s list of best dive bars in the South, honestly, they feel too fancy to rank dive bars, anyway.
Alabama Jack’s is a must-stop for me every time I head to the Keys. I don’t feel like I’m really in the Florida Keys until I see the sign.
Caribbean Club is a vital part of Key Largo’s cinematic history. You can see its exteriors in the classic hurricane/mobster flick, Key Largo.
Whistle Stop in Islamorada has something called 4-Pig Pizza and, um, yes, please.
Holiday Isles Tiki Bar is the reason anyone has ever had a rumrunner. They invented it.
The O.V. on Windley Key has ties to the NFL.
Brass Monkey in Marathon is open until 4 a.m. every morning.
No Name Pub isn’t really on No Name Key, but it doesn’t matter. Watch out for rogue key deer. I’ve seen them try to get into a minivan with someone. Yes, they’re cute. Yes, it’s illegal to touch them.
Sloppy Joe’s is an institution. Is it really a dive bar, though? Meh. Stop in and decide for yourself.
Captain Tony’s was the icehouse, morgue, bordello, cigar factory, a bar called the Blind Pig… and it was the original Sloppy Joe’s. Sloppy Joe Russell rented it, Brad says, for $3/week.
And here’s the Florida dive bars podcast that started it all:
Earlier this summer, I went on a side quest to find. the best fish dip in the Florida Keys. It was a delicious adventure, and although it requires more research, here’s what I found — so far.
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