Free Willy movie, whale jumping to freedom
Free Willy

I would soon be naked.  I was visiting Key West for the first time, and staying at an all male, clothing-optional gay resort.  I had given myself an assignment.  I would free my inhibitions, free my insecurities, free my… Willy.  Now, I am not shy.  I don’t specifically have issues with nudity.  Yet I must admit I was a bit nervous about the nude resort experience.  Why? Was I concerned people would look?  Was I afraid people wouldn’t?

As I approached my soon-to-be, nudity-inspiring home, I was instantly charmed by the white wooden siding, covered porches and lush vegetation of the Island House exterior. As I roamed the resort, met the staff and chatted with guests, I was quickly seduced by the ease and friendliness that comprise its core.  I can totally do this.

On our introductory tour I learned that the Island House is the oldest gay resort in the world, established in 1976 at a time when Key West was a sweet, teeny bait of a town, dangling off the Florida fishing rod.  Much has changed since those days:  Key West, today, is more accessible, commercial and culturally diverse.  The Island House has expanded and remodeled to include a heated outdoor pool, two hot tubs, gym and sauna area, 24-hour café, and full service bar.  Yet both the island and the House are ruled by Key West’s official slogan of “One Human Family,” an inclusive, live-and-let-live philosophy that celebrates us all.  I was happily hooked.

The first day was about acclimating, decompressing and taking it all in. On day two I’d let it all hang out.  I emerged into the 82˚ morning wrapped in only a towel.  I took one step out of my hotel room, pivoted and returned for a pair of shorts.  Breakfast first, then… I told myself.  The poolside café’s ham, egg and cheese sandwich on an English muffin (they were out of croissants that day) was delicious.  And I’ll take a breakfast Rum Runner over OJ any day of the week.  Soon. I laid on the sun deck an ordered a drink, then another.  It was very hot; I was very thirsty.   By the time my sweat had drenched the waistband of my shorts, Willy pleaded for fresh air.  Now or never.  I downed my fourth drink, sucked in my belly and threw shorts to the wind.

Properly SPF’d to avoid a potentially uncomfortable trip home, Willy greeted the Florida sun. Together, we met new friends from San Francisco, Amsterdam, New Haven, Ann Arbor and Sharon Springs, and sipped a few more of those Run Rummers… Rum Rummers… Rum Runners.  It turns out many of our new pals had met each other during previous stays at the Island House, continued their friendships and had actually coordinated reconnecting at the House for subsequent vacations.  Our group effortlessly integrated the curiosity of new acquaintances with the comfort of old friendships.

The most remarkable aspect of being naked was how unremarkable it was.  At times I was naked; at times I was not.  Some of the guests were naked; some were not.  I never felt pressure to… I never felt pressure.  Period.

Perhaps it was the blazing sun, the beautiful location, the new best friends, or the ever-flowing sweet, fruity cocktail concoctions.  Most likely it was the combination of them all.   I realized that full southern exposure at the southernmost point in the continental United States was not the goal.  Disrobing is simple.  Stripping free of preconceptions and insecurities was the challenge.  Dropping my guard—not my shorts—was the key to unlocking the Island House experience, and being welcomed as a happy, new member of One Human Family.

Pool of Island House Key West
Island House, Key West

For more information on the Island House or for a full (frontal) photo tour of the facilities, visit the Island House website.

To learn more about Key West, visit the websites for The Florida Keys & Key West and Gay Key West.

4 thoughts on “Key West: Free Willy

  1. I love Key West! Free Willy indeed . . . perfect place to let it all hang out. Fun article, Ivan.

  2. I love this blog.. I just so happen to be that I am reading this post from my bedroom, overlooking the pool at Island House. Oh.. Yes, my willy is free too!!!…

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