Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Robert Albury “Key West’s King of Soul”
A homegrown Key West talent, Robert Albury, grew up on the corner of Amelia and Whitehead Streets in Bahama Village. Robert had nine brothers and they all sang. Young Robert Albury was most inspired by Louis Armstrong's performance in Key West. To Robert, the vocals of Soul music come from deep down within a special place in your heart. He says, “That’s what makes soul music so great.”
1st Annual Christmas Tiki Olympics
Get ready to "Get Freaky at the Tiki" as Looe Key Tiki presents its 1st Annual Christmas Tiki Olympics on Saturday, December 13th, starting at Noon. This festive and quirky competition requires teams of 4 to 6 players to compete in 5 rounds of funny Christmas games, plus one player from each team will participate in a separate chicken wing eating contest.
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Die Hard
Part of the “Saints, Sinners & Scream Queens” Film Series
Sponsored by the Key West Film Festival
December 18 | 7:00 PM | $15 | Williams Hall
The most chaotic “Christmas movie” ever made. Terrorists, duct vents, Hans Gruber, and one barefoot cop who refuses to quit. A holiday classic by accident. Come celebrate the holidays the loud way.
Holiday Lights Trolley Tour
Join the Key West Parrot Head Club on a Holiday Lights Trolley Tour!
We will meet at Salute restaurant at 4:30pm to check in and get your wrist band. One drink (beer or wine) is included. Additional beverages can be purchased at happy hour prices. At 6:00 will walk over to the White St pier parking lot to board the trolley/train.
See all the best decorations on our holiday tour as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition!
The trolley leaves at 6:30pm sharp!
Christmas on the Keys! Piano Concert with James T. Slater!
Join us for Christmas on the Keys, a joyful, high-spirited piano concert featuring the incredible James T. Slater—two-time Grammy-nominated, piano-playing, bilingual singer-songwriter of Bolivian American descent. Signed to BMG Music Publishing/Nashville, James will be performing hits recorded by legends from Carrie Underwood, and Kenny Chesney, to Tim McGraw and Willie Nelson, to Keith Urban and Enrique Iglesias...as well as songs off his latest album, Shrimp Boat Sessions, recorded LIVE on the piano at Jimmy Buffett's Shrimp Boat Studio here in Key West.
Ian Maksin: New Album Release Tour
Get immersed in the deep sounds of Ian Maksin's soulful one-man-cello orchestra, paired and blended with his vibrant voice, as he explores a collection of traditional songs from different corners of the world: Japan, Finland, Bosnia, Iran, Ukraine, Armenia, India, Kyrgyzstan, and Medieval France and Spain, woven together with original instrumental works.
His latest release Lullaby for the World is an amazing multilingual journey in search of peace, healing and empowerment through music. It reflects the path of a true musical globetrotter, shaped by countless journeys across continents as a touring artist, along with mountaineering, flying airplanes, practicing meditation, and collaborating with local musicians in search of the mystical thread that connects all cultures. This album invites listeners into a space of presence, clarity, and emotional restoration.
Bougie Afternoon Tea Party
Mark your calendars for the second annual Key West Woman's Club Bougie Afternoon Tea Party on January 17th! This delightful event will benefit Take Stock In Children, with a $25,000 Monroe County scholarship to be awarded.
In addition to enjoying a lovely afternoon, there will be prizes for the most elegant attire, so bring your best bougie outfits, hats, shoes, and coats! Camille Russo Toler will provide charming musical entertainment while we sip tea and specialty cocktails. Don’t miss out—GET YOUR TICKETS NOW!!
Darcy Cooke Celebrates Great Women of Song: Timeless Voices, Unforgettable Music
Called a “swinging jazz singer…displaying versatility and a beautiful voice” by jazz journalist, Scott Yanow, Darcy’s “warm and inviting voice” exudes a depth of emotion that draws in and thrills her audiences. With a love of jazz and a background in theater, Darcy is a master of song interpretation and an engaging storyteller who effortlessly guides and charms audiences through an evening of pure entertainment.
Tropical Luncheon & Garden Party
Step into an afternoon of island elegance as the Key West Woman’s Club revives its charming 1950s Tropical Luncheon tradition. Enjoy conversations with bestselling author Lucy Burdette, a preview of KWAHS’s Smithsonian-affiliated exhibit FOOD: Celebrating Conch Cuisine, and insights from curator Dr. Cori Convertito. Chef Martha Hubbard adds culinary flair to this celebration of the flavors and stories that define the Keys.
A delightful blend of history, culture, and island charm — all in the heart of Old Town.
The Wearable Art Fashion Show
Looking for an afternoon of breathtaking art and bold fashion?
Don't miss the Key West Woman's Club's Wearable Art Fashion Show 2026.
Experience the thrill of the runway, where high fashion meets high stakes. Witness the debut of one-of-a-kind, handcrafted creations from our city's most innovative local designers. As each unique piece is revealed on the catwalk, it becomes available for live auction. This is your chance to acquire a signature work of wearable art directly from the designer and take home an unforgettable piece of fashion history.
Your attendance also supports "Creativity in Design" scholarships for Key West High School students.
The College of the Florida Keys 60th Anniversary Celebration
Toast to six decades of educational excellence at The College of the Florida Keys’ milestone 60th Anniversary Celebration, featuring fine dining, cocktails, historical exhibit, live music, and dancing in honor of the College's rich legacy and continued commitment to student success.
4th Annual FRLA Monroe R.O.S.E Awards
The ROSE (Recognition of Service Excellence) Awards recognizes Monroe County front line hospitality employees who demonstrate excellent customer service. These industry champions showcase the region’s commitment to creating an extraordinary visitor experience.
Sponsorship opportunities available.
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
An Enchanted Evening in the Key West Gardens at Fort West Martello – Past, Present & Future
Join us for a very special evening amid a magical display of lights and tropical beauty as we honor 70 years of our beloved Key West Garden. Hear from some of our “keepers of the fort” as we celebrate the past, present and future in a visual display of lights, and garden history and as we share our exciting vision to continue to build on Key West Garden’s legacy.
Best of Key West Jazz Concert
Come feel the magic of the best jazz musicians in Key West! The Key West Jazz Allstars will wow you. Enjoy music and dancing. Full Menu is available from Olive's Mediterranean Cafe.
Parking Lot is at 201 Truman, enter lot off of Emma St, about a block away.
An Evening of Cinema and Celebration: A Fundraising Birthday Fête for Sir Billy Connolly
Join us for a sophisticated evening celebrating the birthday of the legendary actor and comedian, Sir Billy Connolly, with his wife, Lady Pamela Stephenson Connolly.
This exclusive gala is a fundraiser for the Key West International Dance Company (KWIDC). By securing your place, you are providing vital support for the artistic endeavors, community outreach, and educational programs that enrich the cultural fabric of Key West.
Your attendance helps ensure the future of professional dance in our vibrant community. Secure your tickets now for this memorable celebration of cinema, artistry, and philanthropy!
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Strange Journey: The Story of Rocky Horror
Join host Landon Bradbary as we celebrate the 50th anniversary of Rocky Horror. Strange Journey: The Story of Rocky Horror is a joyful and wild ride through the tale of the cultural juggernaut that is The Rocky Horror Picture Show. From its humble origins as a London fringe theater play, the documentary tracks its meteoric rise, fall and resurrection to become the biggest cult film of all time. With intimate access to its creator Richard O’Brien and other major players such as Tim Curry, Susan Sarandon and Lou Adler, the documentary explores what makes the play and film so singular: Its groundbreaking and transgressive themes, iconic performances and epic songs that took over popular culture.
Shorts & Sips
Presented in partnership with the Key West Film Festival
Join us for a cinematic evening that pairs global storytelling with great wine. The night kicks off with a selection of international documentary short films - including the latest film from from Emmy Winner Ondi Timoner - followed by a curated wine tasting featuring bold reds, crisp whites, and light bites. Stick around as we shift gears for a second block of shorts guaranteed to deliver big laughs—our comedy selections, hosted by Tom Dustin of Key West Comedy.
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
PAUL MENTA BUTTERS YOU UP!
Prior to the Spotlight screening of Billy Corben's CANCELLED: THE PAULA DEEN STORY, let Paula's good friend, legendary chef and rum distiller Paul Menta, butter you up with dishes inspired by the cuisine of Paula Deen. Paul will be joined by Billy as they force you to unbuckle some of the notches on your belt buckle while you wash down the delicacies with a selection of Longoria Wines from the Santa Barbara Wine Country.
Your meal includes a ticket to the premiere of the film, playing immediately afterwards at Williams Hall and featuring a Q&A with Miami-based director Billy Corben (Cocaine Cowboys, Screwball, The U)
72 Hour Film Challenge!
Join us for the premiere screening of the 72 Hour Film Challenge—where creativity, caffeine, and chaos collide. Local filmmakers had just three days to write, shoot, and edit an original short film. Now it’s time to see their finished work on the big screen. Expect big laughs, wild twists, and plenty of Key West flair as we celebrate local talent and storytelling at its most daring.
Laugh Your Tails Off Comedy Night
Get ready to Laugh Your Tails Off with the Florida Keys SPCA at the Marathon Community Theatre on November 8th!
Join us for a fun evening of laughter featuring talented local comedians, all in support of the Florida Keys SPCA Marathon campus clinic fund! This fund helps us to provide affordable spay/neuter and preventative services to pet owners in our community.
Fall Showcase
Join us for the Drama Club’s 2025 Fall Showcase Fundraiser!
This year’s theme, Coming of Age, explores the moments that shape us — stories of growth, change, and finding our place in the world — all told through the voices and talents of high school students from our Key West community.
Fall Showcase
Join us for the Drama Club’s 2025 Fall Showcase Fundraiser!
This year’s theme, Coming of Age, explores the moments that shape us — stories of growth, change, and finding our place in the world — all told through the voices and talents of high school students from our Key West community.
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Swing Dance Night with the Paradise Swing Band
Step back in time for an unforgettable evening of music and dance! Williams Hall proudly presents Swing Dance Night featuring the high-energy sounds of The Paradise Swing Band, directed by Joe Dallas.
Joining him on stage will be Donna DeForrest, Mark Rose, Hal Howland, and Tony Elitcher—keeping the dance floor alive with classic swing rhythms.
Shoreline Sessions
Get ready for Shoreline Sessions presented by the Southernmost Beach Resort & Guesthouses in Key West! This epic two-day music event features Fortunate Youth and a fantastic lineup of artists.
The Exorcist - One Night Only!
What better place to watch The Exorcist than inside a church? Join us for a devilishly fun night of horror, history, and head spins as Williams Hall hosts a special Halloween Eve screening of the classic that shocked the world. Drinks, snacks, and exorcisms available at the bar.
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
HANGOVER POOL PARTY AT SOMO'S PINEAPPLE POOL
We'll have plenty of food and drink specials, and a live DJ spinning all your favorites, Deep Eddy’s Bloody Mary specials
CHANNEL 3 AND REGGAE LOU & THE KIND BUDZ REHAB POOL PARTY, LIVE AT THE MARKER
Sponsored by Dirty Monkey Banana Peanut Butter Whiskey, this will be a rehab party for the books, as well as to cure your Fantasy Fest hangover! Channel 3 and Reggae Lou & The Kind Budz will have your vibes flowing with their hit, “Key West It Is The Best”, and more! Dirty Monkey drink specials, two pools, and plenty of hungover people watching! FREE! Noon to 5pm. Reserve your spot
Bourbon St Pub's VIP Balcony Bash
Join us for one of the best views of the Fantasy Fest parade on Duval St. from the Grand Balcony of the New Orleans House, 724 Duval St. Don't deal with the crowds! VIP high-end open bar and catered buffet-no need to go anywhere else. Private entrance and restrooms. Free bag of beads to toss to the crowd below! MC'd by John "Ma" Evans. Don't miss this opportunity for a great vantage point to see the parade and a fantastic party.
Saturday Parade Viewing Party
Get ready for the most spectacular event of the year! Vinos on Duval invites you to a special viewing party for the legendary Fantasy Fest Parade.
Located directly on Duval Street, Vinos offers a perfect vantage point to take in all the elaborate floats, wild costumes, and electrifying energy of the parade. Join us on Saturday, October 25th, as Key West transforms into a vibrant playground of "Bedtime Stories & Magical Monsters."
Nightcaps & Nightgowns
A Moonlight Pajama Party Parade Viewing Experience
One night. One view. One unforgettable pajama party.
Kinky Couples Party
The ONLY event exclusively for couples. Join like-minded couples in the Cabaret Bar overlooking Duval Street. A special performance by the world-renowned latex entertainer RubberDoll, including Live Dark'n Dancing. New York DJ Lucas will be sure to get everyone in the mood for some serious playtime!
Exposed Party
10PM-4AM - Event Open to All! The most risqué party of Fantasy Fest! Play in the Poolside Foam Party! Dance the night away on 2 Dance Floors or Splash around in our Pool & Jacuzzi! Black Out & Black Light party inside, and exotic dancers! Rain or Shine.
42nd Anniversary Headdress Ball 2025
Popular Key West entertainer, Randy Roberts will emcee and arrange the show this year. WEOW’s Rudegirl oversees the music. Twelve to Fifteen contestants will hit the stage to show their Headdress creations, judged from the shoulders up, and vie for the first prize of $5,000. Performances by some of Key West’s best local talent from over the years will again be featured. There is bar service and specialty wine; food may be preordered and delivered to your table. Tickets are $320 for a premium table of 4, $270 for a VIP table of 4, with Chair seating at $35 and General Admission (grass seating) at $30.
5th Annual "Rock the Tatas"
Hanks’ Hair of the Dog Saloon presents the annual charity event, Rock the Tatas Contest. Join us in the fight against Breast Cancer October 23rd. Our energetic event will be hosted by the lovely Kirby Myers and DJ Sanaris. Live music afterwards from 9pm to close. Contest starts at 7 PM at Hanks Hair of the Dog Saloon located at 409 Caroline St. First place prize $500 along with a Crown and Sash! With additional cash prizes for second place. Contestants will be judged on Charism, Creativity, and Costume design
Kinky Kandyland
Join us for an electrifying candy-themed party with fantasy drinks, glowing lights, two stages, three bars, and a live DJ. Indulge in candy martinis, ice cream, cotton candy, and more. Sweet, wild, and totally unforgettable. Guests are encouraged to go all out with bright colors, glitter, latex, feathers, LED accents, and over-the-top accessories that fit the candyland fantasy vibe.
LES GREEENE & THE SWAYZEES PAJAMA POOL PARTY TAKE 2 AT THE MARKER!
Get your swimsuit or your PJs (or both!) and come out to party with Les Greene and the Swayzees! Sponsored by Dulce Vida Organic Tequila. 2-5pm.
PAST YOUR BEDTIME: A Surreal Extravaganza
Transforming 801 Bourbon Bar + Upstairs Cabaret + Saloon 1
LIVE MUSIC ORIGINAL ART LOCAL TALENT CIRQUE BURLESQUE DRAG COMMEDIA DELL'ARTE * LIVE ENTERTAINMENT ALL NIGHT LONG
The Hush Hush Theatre is a pop-up theatre exploring new realms of storytelling through live music, dance, burlesque, drag, comedy and cirque. We encourage new talent, original work and the unconventional.