Rediscovering Key West’s queer appeal in three easy steps


IT’S JUST A FANTASY | Key West’s Fantasy Fest in October is among the area’s biggest attractions. (Photos courtesy Florida Keys New Bureau)


Key West’s Fantasy Fest

After all of these years and after so many destinations have “come out” as gay-friendly, Key West retains the title of the quintessential LGBT travel experience.

Key West is simply fabulous — an island utopia that welcomes everyone and a destination where a bicycle and a sarong are all that you could need for a week of relaxation. To understand why Key West is the destination of the year, all that you really need to do is to go back to its roots: guesthouses, water and sunsets.

Navigating your trip to rediscover Key West could be a challenge. Key West has indeed changed over the years. There are more cruise ships, larger airplanes, fewer gay bars and the drag scene is missing the “World’s Oldest Living Drag Queen”— Margo, or David Feldstein —who passed in 2006. The Key West Business Guild is a terrific resource helping LGBT travelers plan their trip.

In October, Key West has one of its biggest events of the year: Fantasy Fest (Oct. 23–Nov. 1), a kind of Mardi Gras-meet-Halloween freak show that raises hell shore to shore. But even if you can’t make those dates, here are three ways to rediscover Key West:

Stay at a guesthouse. To experience the true spirit of Key West hospitality, stay at a Key West guesthouse. The island offers super-exclusive accommodations and upscale international hotel chains. This destination prides itself on good service to the guest, and there are exceptional guesthouses in Key West. Alexander’s Guesthouse and Big Ruby’s are terrific choices for gays and lesbians, especially when traveling together. New Orleans House, Equator Resort and Eden House are just a few of the great choices for the gay, LGBT and the all-welcoming guests.

The big daddy though is the Island House. Consistently offering top-notch service with a consistent and well-trained staff, Island House retains the allure of gay-male travel. It is a destination within a destination. Offering an all-male environment and luxury rooms, fine dining, entertainment and great conversations, Island House delivers superior service. The resort offers great deals for free stays off-season when you buy a winter escape.


Mallory Square is awesome at sunset.

Explore the water and sea life. Dolphin Safari Charters is the perfect small-ship excursion. Super-friendly and handsome Captain Gary (originally from South Africa) leads this voyage into Key West’s pristine waters. Offering a very private and a VIP trip experience, Captain Gary is part teacher and part fun-seeker. Dolphin sightings are almost guaranteed on every trip and a sighting is where the fun begins. A three-hour-plus trip for adults costs $89 plus gratuity. The dock is located at the Banana Bay Resort and Marina and includes free parking. Trips are offered each morning and afternoon.

For more gay-specific water frolicking, Captain Steve runs men-only Blu Q outings that offer snorkeling, swimming and fellowship … and completely clothing-optional once you get away from prying eyes.

Celebrate the sunset. Of course, Mallory Square is the place to toast another perfect day and sunset in Key West. Danger Charters Wind & Wine Sunset Sail is a perfect way to celebrate Key West’s legendary sunsets. Danger Charter boats are custom-built replicas of a type of American sailing craft called a Skipjack. Simply catch the boat at Westin Hotel on Mallory Square for a two-hour sail for a romantic sunset (or an all-day adventure). The ship’s exceptional and friendly crew share with guests an impressive wine and beer selection from around the world for $85–$100.

— Jeff Guaracino (courtesy Philadelphia Gay News) and Arnold Wayne Jones

This article appeared in the Dallas Voice print edition September 18, 2015.