Gay Travel in Key West: Sun-Drenched Days, Tropical Nights

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

    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.

    You will 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, you’ll arrive in Key West with still plenty to explore and uncover.

    Getting Settled & Exploring Old Town Key West

    Alexander’s Guesthouse, a gay-owned and operated retreat that primarily serves the gay and lesbian community, is the perfect place to settle for your gay travel trip to Key West. Michael, one of Alexander’s attentive and helpful personnel, helps with your bags and gives a tour of the grounds. Your balcony overlooks the pool and hot tub, which are nestled among blooming plants, banana trees and other shade trees – the perfect garden sanctuary. 

    After getting settled in, set off on foot to find a late lunch – you can walk everywhere in Old Town Key West. The crew at Alexander’s recommends when asked by guests to 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, you will get 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

    Sunset Celebration & Out on Duval Street

    There is no better place to watch the sunset than at Mallory Square. It’s a romantic sight. Gay and lesbian couples stroll hand in hand alongside straight couples. Walking around, you’ll meet lots of friendly and open people. In the Keys, no one really cares if you’re gay or straight, making gay travel to Key West an enjoyable experience.

    Mallory Square hosts a Sunset Celebration every eveningThe 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.

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

    If you’re in the mood for a fun night outing, 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 is astounding. The performers do 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. Both are popular spots on the gay Key West circuit. 

    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

    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.

    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 – you’ll come to know and love the locals and other visitors.  It’s easy to feel so “at home” and accepted in Key West where "One Human Family" is their official philosophy. There are plenty of opportunities to return for one of the many festivals like Pride Fest, WomenFest and Fantasy Fest.