Let us take you back to a groovy time full of Tom Collins, Pink Squirrels and Greyhounds; when the bikini became every woman’s new purchase, mini-skirts crept into closets and good ol’ Rock and Roll was heard from every radio station and record player in the United States. Dress in your favorite vintage swimsuit, psychedelic […]

Come celebrate the incomparable queen of basically everything, CHER, from 5-8pm! Come dressed as your favorite Cher from any of her famous decades. We'll have Cheraoke (Yes...Cher Karaoke hosted by Randy Roberts!). Themed cocktails, Cher trivia and a Cher look-alike contest (with PRIZES). Don't miss it! Rum Row at The Gates Hotel, 3824 N. Roosevelt […]

You will see a magic carousel of frisky pets and playful owners, all delightfully disguised, stroll, dance and even skateboard across a stage in a fun frolic for fame and fortune! Think you and your furry, feathered or slithery friend have the perfect outfit? 4 categories to enter-$25 each entry; benefits the Lower Keys Friends […]

The History of Sex – as presented by Psychologist, Sexologist and Sex Therapist Dr. Pamela Stephenson Connolly – is an illuminating journey through centuries of human eroticism. Key West is not the only society that openly and ritually celebrates sexual fun and fantasy – as exuberantly expressed in parades and parties during its annual Fantasy […]

Fall under the spell of Peace and Love Woodstock style. It’s tie-dye, flower power, and psychedelic colors hoo-doo style this year at the Schooner Wharf Bar. The Party starts at 7 PM. Cast your votes for the sexiest Hippie Chick & Grooviest Dude at 8:30 PM. For the adventurous, the Body Painting Contest will mesmerize […]

The Smokin’ Tuna Saloon is proud to present the 25th Anniversary of the Original Key West Homemade Bikini Contest. Over $5,000 in cash & prizes. Creativity and attention to detail are the key elements to winning the 1st prize of $2000, Additional cash prizes for 2nd & 3rd place along with prizes totaling over $5,000. […]

Come and dance under the sea at Lucy’s Retired Surfers Bar’s BLUE PARTY! Key West’s newest bar and restaurant is going all out for a night of marine-themed fun featuring live music from Patrick and the Swayzees and then a late night DJ and a body painter! Sip on signature cocktails like Da Killer Whale […]

A first time event for Cowboy Bill's. 10 teams of 2 women will do their best to show you a very sexy pillow fight while 3 lucky judges score their performance. $1000.00 in cash prizes - 1st - $700.00; 2nd - $200.00; 3rd - $100.00 618 Duval Street 305-440-2605

Prepare to see RED! RED decorations, RED lights and RED beach balls. As long as it's RED any costume will do! The DJ will keep you dancing, so you won't want to miss this often imitated but never duplicated party with the zany, off-beat COSTUME CONTEST. Why wait in line?! Pre-purchase tickets at Fogarty's. 227 […]

LUV 2 GLOW! Fantasy Fests Best and Longest Running Glow In The Dark Dance Party. 6 Years Running! House/Tech House & Techno feat. DJS JEVNE, ATNARKO, TOP JIMMY & HERB JAVIER • 21+ • $5 • 9PM - 4AM • New GlowinG VENUE - MARY ELLEN’S BAR • 420 APPLEROUTH LN