Key West: Carefree, Fun and Flamboyant

Enjoy sun-drenched days and tropical nights in a place where closets are only for your clothes.

Living in Southwest Florida for four years, I’m slightly embarrassed that it has taken me so long to make my way south to Key West. The tropical splendor of Florida’s southernmost point has finally beckoned me to make the trip, and I've convinced my friend to tag along. (Actually, it didn't take much convincing!). As much as I’ve heard about Key West’s laid-back character, I can't wait to get there and experience for myself this place where I could live, laugh and just be me.

Heading South

The drive south through the Keys is breathtaking. The brilliant blue-green ocean is dotted with sailboats, catamarans and wave runners; it's obvious that people are out to have an exhilarating day on (and in) the balmy waters.

We find shells, corals and other nautical items crowding the shelves at many of the local shops that line Highway 1, including The Shell Man in Key Largo where you can purchase big, colorful shells at a really good price.

After meandering through Key Largo, Islamorada, Marathon, Big Pine Key and all the other small keys in-between, we arrive in Key West in the early afternoon.

Getting Settled & Exploring Old Town Key West

We check in at Alexander’s Guesthouse, a gay-owned and operated retreat that primarily serves the gay and lesbian community. Michael, one of Alexander’s attentive and helpful personnel, helps us with our bags and gives us a tour of the grounds. We stop and say hi to some of the other guests along the way. When we get to our room, we see that our balcony overlooks the pool and hot tub, which are nestled among blooming plants, banana trees and other shade trees –  the perfect garden sanctuary. 

Our room is spacious with a king-size bed, flat-screen TV and private bath. I'm impressed by the variety of pillows on the bed – two small firm, two big fluffy and two large feather pillows – no matter what you like to sleep on, Alexander’s has the pillow for you.  I later learn that’s how they do everything at Alexander’s – with careful thought to satisfying each person’s needs and wants.

After getting settled in, we set off on foot to find a late lunch – you can walk everywhere in Old Town Key West. The crew at Alexander’s recommended we go to Pepe’s Cafe, a small bar and grill offering the catch of the day, raw oysters and a chowder that is out-of-this-world. There, we got in on a local favorite – the Oyster Race. It's simple: patrons get a number one through five. A shucker begins to shuck five oysters while another person keeps time. The fastest time wins. Each patron with a number matching the number on the fastest shucked oyster gets to choose a key. If the key opens a locked box, the patron wins the money inside (today a lucky winner walks away with $100).

Sunset Celebration & Out on Duval Street

As the sun starts to set, we hear that there is no better place to watch than Mallory Square. It’s a romantic sight. I see gay and lesbian couples strolling hand in hand alongside straight couples, and no one seems to mind. Walking around, we meet lots of friendly and open people. In the Keys, no one really cares if you’re gay or straight.

Mallory Square hosts a Sunset Celebration every evening. Tonight, the square is buzzing with musicians, acrobats, mimes and unicyclists. We peruse vendors selling their wares – jewelry, artwork and hand-painted t-shirts just to name a few.

The sun may be calling it a day, but the night is just beginning

We walk down Duval Street towards what the locals call the Pink Triangle. Rainbow flags are easy to spot on Duval. Many of the establishments are gay-owned or gay-friendly, and they let you know it.

We decide to check out the nightly drag show at a nightclub called Aqua. The crowd at Aqua is mixed, not just gay men and lesbian women, but straight singles and couples also. Patrons vary in age from young adults to retirement-age folks. The drag show was astounding. The performers did more than sing and dance – they delighted the crowd with outrageous and comedic numbers. 

Some other places to visit for great entertainment are 801 Bourbon Street, which also has nightly drag shows at 9 and 11, and Bourbon Street Pub, which has sexy male dancers (for you boys).

Duval Street is also a shopping haven offering everything from beach gear to small, fashionable boutiques. If you enjoy a good cigar, you can get a hand-rolled stogie at one of the many tobacco shops. And on Duval, you’ll have no problems finding a good place to eat.

But Key West isn’t all about late nights.

Out on the Water

The next morning around 10 a.m., we hop on the boat for an all-day, do-it-all water sports adventure on the Party Cat with Sunset Watersports. The day includes jet skiing, snorkeling, water skiing, banana boat rides, wind surfing, kayaking and more.

I don't even have to worry about taking a camera – professional photographers on board will capture your best moments. You can purchase the photos on CD for a nominal fee. Lunch is available, which is the perfect time to meet the friendly staff. During the last hour of the day, draft beer is free and everyone sits together and shares their fun stories.

Heading Back Home

Leaving Key West is a glum day – we have come to know and love the locals and other visitors, but I am especially sad to say goodbye to my new friends at Alexander’s.  I feel so “at home” and accepted in Key West where "One Human Family" is their official philosophy. I will definitely be going back soon for one of the many upcoming festivals like Pride Fest, WomenFest and Fantasy Fest.

Upcoming Events

Key West Pride Festival, June 6-10, 2012
A nine-day event consisting of an array of fun and cultural events including the Grand Parade, AIDS Help Film Festival, pool parties, concerts and the Dog Diversity Day. Enjoy an incredible week celebrating the diverse community in Key West that supports the GLBT community and their allies.

WomenFest, Sept. 6-11, 2011
Join in the southernmost party for lesbians and their friends. Enjoy a wide range of activities including pool parties, a sizzling dance club scene, bull riding, women-only water excursions, art, poetry, theater, live music and comedy.

Fantasy Fest, Oct. 25-29, 2011
This year’s theme is Aquatic Afrolic. Get ready for a mind-blowing week full of parties – the Coronation Ball, the Headdress Ball, the Pet Masquerade and Parade, Celebrity Look-A-Like Contest, a toga party, a pajama party, the Monster’s Ball and the Duval Street Promenade.

New Year’s Eve Celebration, December 31, 2011
As an alternative to shivering in Times Square, join the jubilant crowd around the 700 block of Duval Street gathered in shorts and other summer attire. Watch Key West’s famous drag queen, Sushi, descend in the giant red, high-heel shoe from the top of Bourbon Street Pub to the street below during the countdown to 2011.

This article is brought to you by the Florida Keys & Key West Tourism Development Council. For more information, visit


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