Fantasy Fest: Event Picks


KEY WEST, FL - OCTOBER 30: In this handout pho...
Image by Getty Images via @daylife

Fantasy Fest always brings a bunch of fun events to choose from. Generally, my favorite is the Masquerade March, a parade on Friday night where locals and visitors alike dress up, drink heavily and frolic in the streets, stopping for drinks along the way. In 2009, my shoe broke on the way to parade forcing me to stop at the dollar store and buy size 11 pool shoes (I wear a 7 1/2). Last year, my wig had been put on badly (by me – I need some drag queen lessons, stat) and I had a perfect stranger fix it, after I stopped at her house to use the bathroom. But, there are many good events over the course of the week.

Tonight at the Westin is Pinking of You, a live auction of bras-turned-artwork,

One of last year's entries, courtesy of Mile Zero Mag.

including a fashion show. Proceeds benefit WomanKind for breast cancer education and clinical exams.

Tomorrow night is the famous Headdress Ball at the Southernmost Hotel on the beach. Months are spent preparing the elaborate headdresses. This is one of the events that usually sells out, so get your tickets ahead of time.

Wednesday is the Pet Masquerade at the Casa Marina to benefit the Lower Keys Friends of Animals. I have to say, being a new dog owner I am pretty bummed that I will be out of town for this one. Next year, watch out, Babka will be in full costume.

Thursday night try the Pretenders in Paradise costume contest at the Pier House, and see what creative outfits are part of this year’s festivities.

Friday night, as I mentioned above is the Masquerade March. It is always a good time, so grab your drinks in a to-go cup and start marching.


Fantasy Fest, Key West
Image via Wikipedia

Saturday night is the Captain Morgan parade. Personally, I think this is the weakest part of Fantasy Fest. By Saturday night, most of us have seen enough naked people, and I certainly don’t want to be standing 6-deep on Duval street waiting for floats to go by. If you can snag an invitation on a float, go for it. Otherwise, be sure to find yourself someplace with seating, and preferably a restroom.

What is your favorite event?

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