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A Keys classic since 1938, Caribbean Club is a laid‑back bayside dive with big Florida Bay views and a bit of Hollywood lore—the exterior featured in the Humphrey Bogart film Key Largo and it later popped up in Bloodline. It’s unpretentious, loud when it wants to be, and exactly the kind of salty stop that makes the Overseas Highway fun.
Come for the sunsets and stay for the scene. The waterfront deck is the prime perch as the sky goes pink, and the crowd skews local and friendly. Live music runs most of the week (typically Thursday–Sunday), with karaoke on Wednesdays; if weather turns, the show moves indoors. Drinks are reasonably priced, and the vibe is festive rather than fussy.
You’re here for cold drinks and Keys atmosphere, not white tablecloths. Expect solid cocktails (Key Lime Pie–style rum punch gets shout‑outs) and beer. Hungry? Food trucks set up right out front most days, operating as separate businesses, so you can grab tacos or a sandwich and wander back to the bayside seating.
Sunset is the headliner here. On Fridays and Saturdays the place surges from early evening through late night; arrive 30–45 minutes before sunset if you want a waterfront table and an easy parking spot. Weeknights are more relaxed but still lively when bands are playing. Daytime visits are mellow and scenic if you’re road‑tripping and just want a quick bayside pause.
