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15 Feb 2024 Blogs
The Upper Keys, stretching from Key Largo to Islamorada, offer a blend of stunning ocean views, warm tropical breezes, and some of the most authentic dive bars you'll ever come across. These watering holes are not your average bars—they are slices of local culture where the vibe is laid-back, the drinks are strong, and the stories are as colorful as the sunsets. Whether you're a local, a road-tripper, or a vacationer looking for the perfect low-key hangout, these dive bars in the Upper Keys are sure to leave an impression.
The Caribbean Club is a legendary spot in Key Largo, famous for its role in the 1948 classic movie Key Largo starring Humphrey Bogart and Lauren Bacall. Today, it’s a magnet for locals and visitors alike. This bayside bar offers cheap drinks, live music, and a no-frills atmosphere with one of the best sunset views in the Keys. Bring cash—they don’t accept cards—and enjoy a beer while soaking in the Old Florida charm.
Sharkey’s combines the vibe of a dive bar with the allure of a waterfront setting. Nestled by the marina, it’s the perfect spot for a cold brew after a day on the water. Their happy hour is a hit, with affordable drinks and a menu featuring surprisingly good eats like fish tacos and conch fritters. Sharkey’s draws a mix of locals and visitors, making it an ideal spot to trade fishing tales.
Technically a little off the beaten path, Alabama Jack’s is a must-visit institution on Card Sound Road, the scenic back route to Key Largo. This open-air shack is the epitome of rustic charm, serving up ice-cold beers and their famed conch fritters. With live country music on weekends and an eclectic crowd that includes bikers, boaters, and families, Alabama Jack’s is a true Florida Keys experience.
While some might argue it’s too polished to be a “dive,” the Pilot House’s bar still captures the laid-back essence that makes dive bars so beloved. The star attraction here is the glass-bottom bar that lets you peer into the marina below while sipping a cocktail or beer. It’s a little quirky, a little nautical, and a whole lot of fun.
The "O.V." as locals call it, is an Islamorada institution. Owned by former NFL player Gary Dunn, this casual bar and restaurant is a favorite for its unpretentious vibe and hearty pub fare. There’s an outdoor tiki area, plenty of TVs for sports enthusiasts, and live music that keeps the party going. It’s the perfect spot to kick back after a long day of fishing or snorkeling.
While Lorelei might lean a little more toward tourist-friendly than true dive, it earns a spot on this list for its iconic status in the Upper Keys. Its relaxed tiki bar ambiance, affordable drinks, and live music make it an easy favorite. Watching the sunset here with a rum punch in hand feels quintessentially “Keys.”
This low-key spot has a true dive-bar feel tucked into a marina setting. Whale Harbor offers a mix of locals, anglers, and those in the know who appreciate its rustic charm. Pair a cold drink with the unbeatable view of fishing boats coming and going, and you’ve got a recipe for a perfect Keys evening.
What makes the dive bars of the Upper Keys so unique is their unpretentious vibe and connection to the surrounding beauty. These are places where the conversation flows as freely as the drinks and where you’ll find yourself striking up a chat with fishermen, locals, or fellow travelers. They’re the antidote to over-polished, high-end establishments, offering a slice of the real Florida Keys—relaxed, welcoming, and wonderfully authentic.
So, next time you’re heading down the Overseas Highway, make time to stop at these iconic spots. You’re not just grabbing a drink—you’re diving into a slice of Florida Keys history and culture.
What’s your favorite dive bar in the Upper Keys? Share it in the comments below! Cheers to good drinks and even better stories. 🥂
