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Caroline's Other Side
429 Caroline Street, Key West, FL, USA
Set back from the busy Duval Street, Caroline's Other Side offers a quieter and more laid-back space to spend an afternoon. This is a cocktail bar like no other on the island, serving craft beer and an extensive wine list alongside classic cocktails with a twist inspired by the city. The decor is old school but stylish, letting you enter another world the moment you step through the door.
Gay Friendly, Cocktails
Good for:
Popular bars in
Key West
Bourbon Street Pub
Key West's original and only video bar brings a New Orleans inspired space to this small-town gay scene. The venue includes a male only garden bar where clothing is optional, and you'll find guys hanging out by the pool or in the jacuzzi. See what's on in the theatre space or head inside for one of the other bars. There are regular themed nights, drag shows, and cute dancers to entertain a mostly male crowd.
Bobby's Monkey Bar
This is a truly local gay bar that's been a meeting place for community for years. As the name suggests, Bobby's Monkey Bar is a themed bar with monkey memorabilia around the bar and throughout the venue, making this a fun place that all gay visitors will want to experience. It's a place to meet locals and really be immersed in the Key West gay scene, with karaoke, daily happy hours, and a super laid-back crowd.
One Saloon
This unassuming place located in the Bourbon Bar complex is the only male only leather bar in the city, catering to a super masculine and pretty cruisey crowd. There's a dungeon to explore, regular themed nights, drinks specials, and a welcoming atmosphere that lets you party however you like until late. Every Friday at midnight the bar hosts "Cock Shot".
Aqua Bar and Nightclub
Located on the historic Duval Street, Aqua is the life of the Key West gay scene. It hosts drag shows, karaoke, and other live entertainment throughout the week, and you can dance late into the night thanks to the in-house DJs. Great value happy hours and all your favourite bar food keeps the party going, while out back there's a quiet garden bar that's the city's best hidden watering hole.
801 Bourbon Bar
Located on historic Duval Street and just a few minutes from Ernest Hemingway's House, 801 Bourbon has been central to Key West culture for years. This multi-story complex hosts cabaret featuring The World Famous Drag shows every night, and there's also live music, karaoke, and bingo nights. The bar serves speciality drinks that change daily, and the space is a well established staple for the local gay community.
La Te Da
The Cabaret & Piano Bar at La Te Da, located on the iconic Duval Street, isn't specifically a gay bar but it welcomes everyone to join the fun. This is a more upscale venue, featuring a terrace bar as well where you can sit and enjoy the Florida sun. The Cabaret & Piano Bar has a packed calendar of performances, the venue's kitchen serves up delicious food, and there's always a lively atmosphere.
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