Stay & Play: Key West, Fla.

Don’t miss our latest news! Sign up today for our free newsletter.

Enter Your Email *

Out Traveler Newsletter

Subscribe To
OUT MAGAZINE

Print >Digital>

Give a gift • Renew

watchlive

Search form

Scroll To Top

By continuing to use our site, you agree to our Private Policy and Terms of Use.

Florida Keys

Stay & Play: Key West, Fla.

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

Jesse Steinbach

March 18 2016 2:40 AM EST

March 07 2023 11:18 AM EST

1. Hemingway Hous
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 the grounds.

2. Sunset Cruise
If you are partial to a drink or two, why not embark on a booze cruise? (You are on vacation after all.) The friendly, knowledgable staff will keep you sated by plying you with a selection of international and domestic wines paired with a variety of cheeses. A few glasses in and you'll get to see one of the most stunning sunsets in Key West.

3. Aqua
This watering hole is well-known for its affordable drinks, cheerful staff, and vibrant drag performances. And, although, the divas here perform mostly on-stage, they aren't afraid to wander the bar floor and rope some patrons into the act too.

4. Bourbon Street Pub

Arguably the most popular (and largest) gay bar on Duval Street, Bourbon Street Pub has multiple rooms catering to a variety of interests: from the go-go boy dance area and pool-side bar to the discreet mancave hidden in the back. There should be plenty of opportunity to meet locals and visitors alike at this Key West haven.

5. Island House
Part hotel, part restaraunt/party complex, Island House also offers 24/7 clothing-optional pools, steam rooms, and hot tubs. After a night out on Duval, this is the perfect place to end your night with one last drink and a quick dip before turning in.

Florida Keys

Be sure to follow Out Traveler on your favorite social platform