A Perfect Night OUT in Key West

5 Out Travelers. 1 Gorgeous Destination. This is OUT in Key West.

Last year, OUT sent newlyweds Kit Williamson and John Halbach on a romantic getaway to our favorite gay mecca. This year, the pair are back in Key West, and they brought some friends. Join Kit and John with their pals, Adrian Anchondo, Stephanie Frosch, and Anna Campbell for some glorious Florida sunshine, island adventure, and endless Key Lime Pie. Follow along as Kit, John, Adrian, Stephanie, and Anna take you OUT in Key West. 

Key West may be a small island, but it has packed in a lot of nightlife. There’s dancing to be done, drinks to be had, shows to be seen, and new friends to be made. This is our perfect night in Key West.

START (OR END) YOUR NIGHT WITH DRINKS AT BOURBON ST. PUB & NEW ORLEANS HOUSE

New Orleans House

In the heart of Duval St., the Bourbon St. Pub at New Olreans House is a staple of LGBT nightlife in Key West. From day to night, the front bar is packed with energy, and guys can head towards the back of the bar, where there's an all-male area with a swimming pool, hot tub, and spearate bar area to hang out. 

Kit’s Tip: When I was 16, I had my first kiss at a gay bar in New Orleans, and New Orleans House reminds me so much of that amazing city. There are a bunch of different areas, including a clothing-optional patio with a swimming pool in back and a balcony upstairs in the front where the iconic local drag queen Sushi stores the oversized high-heeled shoe she uses to ring in every new year. Definitely swing by here for a little taste of the big easy.

John’s Tip: If you’re looking for daytime fun on the weekend, stop by on Saturday between noon and 5 p.m. for their pool party, or on Sunday for $20 bottomless mimosas and bloody marys from noon to 4 p.m.

CHECK OUT THE DRAG SHOW AT AQUA

Aqua Resized

This bar and nightclub located on Duval Street is known for their nightly drag shows featuring the Aquanettes.

John’s Tip: I love a drag show, and Aqua has amazing shows with incredible queens seven nights a week. You can call ahead to make reservations to make sure you get seats up close and personal with the girls. Don’t forget to tip!

Kit’s Tip: I love making a fool of myself at karaoke, (“Alone” by Heart is my signature tune) and Aqua has amazing karaoke Monday through Thursday night at 11 p.m. They also have a 2-for-1 happy hour every day from 5 to 7 p.m. that I’d recommend checking out. You know… If you’re feeling nervous about singing.

DANCE THE NIGHT AWAY AT SIDE BAR

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Key West’s newest gay bar, Side Bar comes to us from the owners of Aqua.

Kit’s Tip: They are leaving the drag shows to Aqua and focusing on bringing the dancing to Side Bar. It’s a chill place to hang with friends just off the main drag.

John’s Tip: There’s also a pool table and they stay open late if you’re looking for an after-hours club.

Find all this and more waiting for you out in Key West. Plan your adventure here, and streamline your travel by flying directly to Key West International Airport from a variety of connecting cities, including Newark, NJ, Charlotte, NC, Atlanta, GA, Miami, FL, and more.

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