Step into Aqua Nightclub on Duval Street, and you're not just entering a bar; you're stepping into a spectacle. This isn't merely a place for a drink; it's an immersive experience. The downstairs bar pulses with energy, setting the stage for the real magic found upstairs. Here, Key West’s largest and most dynamic drag house takes center stage nightly, serving up unforgettable cabaret performances that are as hilarious as they are dazzling. Expect soaring vocals, incredible costumes, and quick-witted banter that will keep you captivated. And while you're there, be sure to sample their famous frozen concoctions – the perfect complement to a night of fabulous entertainment.
For decades, Bourbon Bar has stood as an iconic cornerstone of Key West's gay nightlife, embodying the island's free-spirited essence. More than just a bar, it's a multi-faceted entertainment complex. Imagine five distinct bars under one roof, each offering a slightly different vibe, ensuring there’s a perfect spot for every mood. Bourbon Bar is synonymous with electric live VJs spinning tunes, captivating live shows featuring the legendary "Men of Bourbon" nightly, and a raucous atmosphere ripe for celebration. Whether you're in the mood for a friendly game of pool, joining the island's largest karaoke book for a sing-along, or simply soaking in the vibrant atmosphere, Bourbon Bar delivers.
One of Bourbon Bar's most talked-about features is its unique Garden of Eden rooftop bar. This "clothing optional" oasis offers a truly liberating experience, providing a bird's eye view of the island and a refreshing sense of freedom under the stars. It's a testament to Key West's embrace of personal expression and uninhibited joy.
No visit to Key West is complete without stepping into the legendary Sloppy Joe's Bar. For generations, this iconic saloon has been a beacon of live music, generous drinks, and an endlessly engaging crowd. Famously associated with Ernest Hemingway (though its location shifted from its original spot), Sloppy Joe's perfectly encapsulates the island's laid-back yet lively spirit. Its spacious interior buzzes with activity, offering a quintessential Key West experience.
One of the most engaging ways to experience the perpetual party at Sloppy Joe's, even before you arrive, is through its renowned live bar cam. Situated strategically at the front, the "Crowd Cam" offers a tantalizing glimpse into the bustling life of Duval Street and the perpetual motion inside. It’s a virtual window into the heart of Key West’s revelry, letting you literally people-watch from anywhere in the world.
For fans of Jimmy Buffett and anyone seeking a dose of quintessential island escapism, Margaritaville on Duval Street is an absolute must. This isn’t just a bar; it’s an ode to the "Key West National Anthem" and the carefree lifestyle it embodies. Bartenders are often happy to share tales and anecdotes that deepen your appreciation for Buffett's connection to the island. Here, you can chill with a perfectly crafted margarita, listen to your favorite tunes, and truly immerse yourself in the relaxed rhythms of the Keys. The combination of fantastic food, enchantingly tropical drinks, and an ongoing dance party means you might just find yourself wanting to spend your entire trip here. It’s the ultimate embodiment of island time.
Stepping into Blue Heaven is like entering a whimsical, living art installation. This al fresco dining gem on Petronia Street is pure Key West style, sheltered by canopies of tropical foliage and adorned with improvised art – think leopard-spotted mannequins, a "rooster graveyard," and jolly-colored coconuts. The atmosphere is as famous as the food, with chickens and resident cats casually roaming the premises, adding to its quirky charm.
But Blue Heaven is more than just a feast for the eyes; it's a place steeped in history. The property has hosted cock fighting, gambling, and even Friday night boxing matches refereed by none other than Ernest Hemingway himself. The outdoor courtyard is literally paved with slate pool table tops from its days as a billiard hall, and the second floor once housed a dance hall, a bordello, and a playhouse. Today, the "Bordello Gallery" above the restaurant still offers a peek into tiny rooms through sliding peep holes, hinting at its colorful past.
The culinary journey at Blue Heaven matches its unique ambiance. Their specialties include exquisite Caribbean cuisine, fresh seafood, and thoughtful vegetarian dishes. Chef Dan, with a deep understanding of the island's flavors, crafts dishes that have earned legendary praise – one journalist even quipped that his scallop sauce "would make cardboard taste good." From the savory Black Grouper with key lime honey glaze to a warm cucumber and red onion salad, every plate is a testament to the island's rich culinary heritage. Just remember the house rules: enjoy the food and ambiance, keep an eye out for falling almonds or coconuts, and definitely "no swinging from the water tower on the rope swing!"
Nestled in the heart of historic Old Town Key West, Island Dogs Bar offers a breezy, authentic experience where locals and visitors effortlessly mingle. This is the place for genuinely friendly bartenders, consistently delicious food, and a relaxed atmosphere that encourages lingering. Beyond the cheap drinks, you’ll find an impressive menu of tropical cocktails and one-of-a-kind martinis that elevate the experience. With live music often filling the air, Island Dogs Bar provides the perfect backdrop for a casual afternoon unwind or a lively evening among new friends. Their "Pirate Punch" is a local favorite, perfectly embodying the spirit of the Keys.