With a group of thirty guys anxiously awaiting to enter the route for the Key West Pride Parade, we make our way towards Duval Street on the Island House pride float.

The sun shining down, and Lady Gaga blaring, I pull my blond locks out of my face and adjust my dress. Wait a second! Last I remembered, I didn’t dress in drag and look like Christina Applegate in a tiny red dress.

Oh well! Another Key West first for me, the sun is either going to my head or the “live and let loose” attitude of Key West is rubbing off on me. 

Either way, I’m having the time of my life and don’t really care!


With 7,000 visitors in town for Key West Pride, the gay hotels are full and the city is bustling with excitement.

With a few dozen of the hotel guests dancing on the Island House float from Germany, the UK, Switzerland, New York City, and San Francisco, Key West clearly continues to be a gay hotspot with their accepting culture, outdoor excursions, fresh food, sun and beaches.

With Key West’s community being as inviting and talented as it is, this pride weekend proves to be one of the most entertaining and engaging I’ve ever experienced!

Turning to Shawn, a local who is also dressed in drag and one of the bartenders I met at the Island House, we can’t help but laugh at the situation we’ve found ourselves in. “This is typical!” Shawn says. “With such a accepting and safe environment for people to walk and bike around, you never know where you’re going to end up!”

He couldn’t be more correct! From the Fury Pride Adventure Cruise, clothing optional Moonlight Tea Dance at Sea, and the LGBT bike ride along the coast, I found myself on plenty of fun LGBT excursions while visiting Key West.

Winding our way through Old Town, I’m amazed at the diversity of the crowd and how supportive this city is of the LGBT community. For a city with 25,000 full time residents, the route went on for miles and it felt like everyone was out cheering us on - gay, straight, families with kids, and local business owners.

With the parade coming to an end, we make our way back to the Island House Hotel. With a pool, bar, and restaurant on the grounds, the official Sunday Funday has begun!

After a quick shower to remove the remnants of my Key West drag experience, a celebratory drink, and a round of food, we continue the Key West tradition of a Sunday celebration at Pearl’s Key West, Bourbon Street Pub, and 801 Bourbon Bar where they host the 2nd Sunday Pre-Tea, Hot Tea, and Drag Tea.

While half of the group from the float stopped by Pearl’s, the other half heads on over to the Garden of Eden for a drink and to enjoy some of their last rays of Key West sun.

With gay, and gay-friendly, events like Key West Pride, Fantasy Fest, and Womenfest, Key West lures in 245,000 LGBT visitors a year and has over 259 days of sunshine a year.

Key West continues to be one of those cities that offers a different experience with every visit. While the end of the trip is looming, I ignore the fact and just enjoy the moment!


All I know is Key West is doing something right because I’m already thinking about my next trip down to this welcoming and tropical island!

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