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OUTinKeyWest

Where To Play In Key West

Where To Play In Key West

The island is serving up killer drag performances, strong drinks, and cultural adventures. 

jessesteinbach

Hemingway

1. Hemingway House

Who wouldn't want to get lost in the home of a literary legend? Wander the Hemingway House after taking a quick guided tour (just 30 minutes). Make sure you check out the writer's studio as well as pet one of the six-toed cats who meander around the grounds.

Sail

2. Sunset Cruise

You're on vacation, so a booze cruise is always in order. Enjoy a selection of international and domestic wines, a variety of cheeses, and friendly, knowledgable service aboard this boat. A few glasses in and you'll get to see one of the most stunning sunets in Key West.

Aqua

3. Aqua

Head over to Aqua for affordable drinks, a cheerful staff, and vibrant drag performances. The queens here perform on the stage, but aren't affraid to wander the bar floor either. Hey, you might even be asked to join in!

Bourbon

4. Bourbon Street Pub

Arguably the most popular (and largest) gay bar on Duval Street, Bourbon Street Pub has multiple rooms catering to every nightlife taste: go-go boy dance area, pool-side bar, even a discreet mancave hidden in the way back. You'll meet locals and visitors alike at this Key West haven.

Island House

Part hotel, part restaraunt and party complex, Island House offers 24/7 clothing-optional pools, steam rooms, and hot tubs. It's the perfect end to a night of bar-hopping on Duval. Grab yourself one last drink and take a dip before calling it a night.

30 Years of Out100Out / Advocate Magazine - Jonathan Groff and Wayne Brady

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Jesse Steinbach