Five Commandments for a Fall Getaway to the Gay Paradise of Key West

fall key west

If you’ve already had your fill of pumpkin spice and casual cardigans, consider a blissful return to Speedos and sandals on a Key West getaway. While northern gay outposts like P-Town and Fire Island start to clear out for the colder months, the party is still hot in Key West.


From world-class cuisine to cultural attractions, there’s plenty to keep all kinds of visitors entertained. However, Key West’s vibrant queer history makes it a special destination for LGBTQ travelers. The queer community is the lifeblood of Key West, helping maintain the island’s “One Human Family” ethos. It’s not just the gay bars, guesthouses and Pride celebrations. Key West celebrates its queer community year-round and last year elected an openly-lesbian mayor.

Key West bills itself as “Close to perfect, far from normal,” so don’t expect a typical tropical trip when you visit the Conch Republic. To help get you in a Key West state of mind, we’ve put together our list of Five Commandments for the Key West Traveler:

Pack Light:
Don’t let hefty baggage fees deter your travel plans. With a trip to Key West, it’s easy to leave the luggage behind. All of the LGBTQ guesthouses have at least a clothing-optional section, if not a full nudity-friendly facility. You’d be surprised how much space you save in your suitcase when you don’t need to worry about swim trunks, tank tops and shorts. If the idea of dropping public trou doesn’t vibe with your vacation chill, don’t sweat it. The overwhelmingly welcoming Key West crowd encourages you to “Come as you are” — even if that’s someone that’s sticking to their swimsuit.

The relaxed attitude extends to evening attire as well. Even Key West’s white linen, fine-dining establishments don’t enforce any sort of fancy dress code. No, you can’t necessarily belly up to the bar in your birthday suit, but you can keep it comfy and casual without any shade or side-eye from the host.

Key Lime Pie at Blue Heaven.

Eat Up:
Speaking of fine dining, there is no shortage of options in the Key West culinary scene. Seafood is, of course, a major component on most menus, but there are palate pleasers aplenty. Many will tell you a meal at Santiago’s Bodega is worth the airfare alone, with the Saganaki served a la flambé providing a picture-perfect Instagram moment. Don’t miss local delicacies, like the hog snapper at Café Solé, spiny lobster or pink shrimp.

Even the greasy spoons, holes in the wall and mom and pop shops have lots of creative cuisine to offer. Pepe’s Café, the city’s oldest restaurant (established 1909), has reliably delicious omelette specials that should be approved by the FDA to medically treat hangovers. Blue Heaven offers an eclectic al fresco experience and, according to some, the best Key lime pie on the island.

Photo courtesy FURY.

Get Wet:
You may be sloshing through snow soon enough, so it’s time for one last splash. If your definition of water activities stops at lounging poolside au naturel with drink in hand, you won’t leave Key West disappointed. However, those with a sense of adventure and a taste for thrills can set sail with Blu Q for a men-only, clothing-optional sail, snorkel and more. You can up the intensity with FURY, signing up for jet-skiing, parasailing and other activities.

There are several beaches around Key West, each offering a little something different, whether that’s soft sand, natural splendor or nearby amenities. Fort Zachary Taylor boasts a popular beach (plus an interesting historic fort that’s a quick tour if you’ve got some time to spare).

Get Wild:
One thing locals and visitors alike share is a love for having a good time. Key West’s nightlife stays mostly concentrated on Duval Street with several gay bars attracting LGBTQ and straight patrons. It’s easy to find a place to rage into the early hours of morning or relax with a generous glass of wine. The proximity of the bars makes it easy so you won’t have to choose between mild or wild on any given night.

The drag shows go down at Aqua and 801 Bourbon Bar, while the go-go boys and nude backyard are over at Bourbon Street Pub video bar.

A glimpse of Island House’s Sunday pool party. Photo courtesy Island House.

Make Friends:
Maybe it’s the gorgeous weather or maybe it’s the pretense that’s dropped along with your swimsuit, but there’s something about Key West that makes people open up. At pool parties, happy hours, late-nights and tea dances, locals and visitors of all shapes, sizes, colors and ages mix and mingle. It’s disarmingly genial, even if your heart has already starting freezing over a bit.

Premier gay guesthouse Island House is a social pillar. Even if you’re not staying there, we recommend a day pass to enjoy the facilities. Weekly pool parties and happy hours bring gay travelers and residents together in a party atmosphere. Even traveling solo, it’s easy to find friends sunbathing or chatting at the exceptional on-site café and bar 24/7.

But don’t take our word for it. Check out this video of Island House visitors reflecting on the memories they made.

Put away the parka and book your next trip to Key West today. Find out more about the fabulous destination of gay and lesbian Key West here.

Published at Thu, 17 Oct 2019 17:25:29 +0000