Brendan Eyre
Brendan Eyre is one of the country's top club and corporate event comedians. His laid back, relatable style has proven a hit with audiences all over the world. He has appeared on Late Night with Seth Meyers on NBC, Comedy Central, Gotham Comedy Live, and his comedy has been viewed over 50 million times on TikTok. He was also a New Face of Comedy at the prestigious Just For Laughs comedy festival and he is heard regularly on Sirius XM radio.
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.
Saturday Wine Tastings at Unity Table: Sta. Rita Hills: Daniel’s Journey in California
Join local sommelier, Daniel McCurdy, for an educational wine experience and food pairing upstairs at Williams Hall’s Unity Table from 2pm to 4pm. Explore the wines of California’s Sta. Rita Hills through a special selection curated from Daniel’s recent travels to the region, accompanied by thoughtfully paired bites from Chef Martha Hubbard.
Unity Table Chef's Dinner: Some Oldies but Goodies
Join Chef Martha Hubbard of Unity Table at Williams Hall for a three-course dinner celebrating the classics that never go out of style. Familiar favorites get Chef Martha’s signature touch for an evening that feels both nostalgic and fresh.
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, Skipper Kripitz, and Tony Elitcher—keeping the dance floor alive with classic swing rhythms.
Nat Baimel
Nat Baimel is a comedian, upbeat problem solver, awkward philosopher, and optimistic nihilist with a knack for always looking on the bright side. His dark, smart, well-crafted material often tackles the most serious of subjects in a silly manner that will make you laugh as much as it will make you think.
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.
Fundraiser for MAC/ Military Affairs Committee
Mac’s Place will host a community Veterans fundraiser for the Military Affairs Committee (MAC) on Friday, November 13, 2026, bringing together local residents, businesses and military supporters for an evening of fundraising, recognition and community connection. The event is designed not only to raise funds for the MAC, but also to introduce more of the Key West community to the organization, the programs it supports and the important role it plays in connecting the local community with military members and families.
Saturday Wine Tastings at Unity Table: Wines for Fall Flavors
Join local sommelier, Daniel McCurdy, for an educational wine experience and food pairing upstairs at Williams Hall’s Unity Table from 2pm to 4pm. Explore a selection of red, white, and rosé wines perfect for the flavors of fall, accompanied by thoughtfully paired bites from Chef Martha Hubbard.
Sunday Wine Tastings at Unity Table: Wines for Fall Flavors
Join local sommelier, Daniel McCurdy, for an educational wine experience and food pairing upstairs at Williams Hall’s Unity Table from 2pm to 4pm. Explore a selection of red, white, and rosé wines perfect for the flavors of fall, accompanied by thoughtfully paired bites from Chef Martha Hubbard.
14th Annual FRLA Wine on the Water
Wine on the Water is a signature fundraising events hosted by the Florida Restaurant & Lodging Association Monroe Chapter. The experience is designed as an elegant sunset cruise with live music featuring A five-course pairing menu with five wine varietals prepared by a local celebrity chef showcasing the creativity and talent of the Florida Keys culinary community.
Film Screening of Mile Zeros: UnAnchored
Get Ready for Local Laughs!
Comedy Screening & Filmmaker Q&A!
Mile Zeros: UnAnchored is a local comedy series filmed entirely in the Florida Keys! Full of fun, inside jokes for locals, Episode 1 takes aim at lobster mini season! In this pilot episode, two eccentric FWC officers (played by Chad Newman and Samantha Jindra) are trying to rack up some lobster season arrests for their scoreboard, when two unsuspecting honeymooners (Darby Sheehan and Luke Wright) go on a snorkeling trip and find themselves in the crosshairs of the two officers. Add in a shady bail bondsman (portrayed by Pedro Lara), and you have the zany world of the Florida Keys captured on film by the people who live it.
Unity Table Chef's Dinner: The Veggie Edit with Chef Abigail: Island Feels
Chef Abigail Houff returns to Unity Table with a monthly vegetarian evening highlighting a specific region or cuisine. Specializing in plant-based cuisine with an emphasis on bright, clean flavors, she has prepared many memorable meals at Unity Table. For her first dinner of the season, she’s keeping us island-adjacent with some Caribbean-inspired flavors!
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.
Greg Fitzsimmons
Greg Fitzsimmons is an accomplished stand-up, a four-time Emmy-winning writer, and a host on TV, radio and his own podcasts. Host of the popular FitzDog Radio podcast, as well as the Sunday Papers and the Childish podcasts, Greg has made more than 20 visits to The Joe Rogan Experience and 50 visits to The Howard Stern Show, and one hundred on The Adam Carolla Show. Howard gave Greg his own show on SiriusXM, which ran for more than ten years. He’s done dozens of appearances on all the late-night talk shows including Letterman, The Tonight Show, Conan O’Brien and Jimmy Kimmel.
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.
Unity Table Chef's Dinner: The Essential Fall Meal
Settle into the flavors of fall with Chef Martha Hubbard of Unity Table at a cozy three-course dinner celebrating the warmth and comfort of the season. Thoughtfully prepared and just indulgent enough, it’s the perfect meal for a November evening.
Saturday Wine Tastings at Unity Table: Aromatic White Wines from Around the Globe
Join local sommelier, Daniel McCurdy, for an educational wine experience and food pairing upstairs at Williams Hall’s Unity Table from 2pm to 4pm. Discover aromatic white wines from around the globe, featuring beautiful floral, citrus, tropical fruit, and herbal notes, accompanied by thoughtfully paired bites from Chef Martha Hubbard.
Pirates and Mermaid Rum Chase
Ahoy, pirates and mermaids! Gather your crew and prepare to Get Shipwrecked at the Garden!
Join us for the Pirates & Mermaids Rum Chase on Saturday, November 21, 2026, from 5:00 to 9:00 p.m. The Key West Tropical Forest & Botanical Garden will be transformed into a tropical adventure filled with delicious drinks, hidden clues, creative costumes, and plenty of pirate mischief.
La Dolce Vita
Kick off the new season with an evening of Italian food, music, dancing, and good friends!
The Key West Woman's Club invites members and one guest to our FREE Members-Only Italian Welcome Back Party.
Joseph Drouhin Wine Tasting Dinner at Unity Table
Join us for an elegant four-course wine tasting dinner celebrating the rich heritage and exceptional wines of Domaine Joseph Drouhin. Founded in Beaune in 1880, Domaine Joseph Drouhin is one of Burgundy, France’s most respected and historic wine houses. Still family-owned today, the estate is renowned for producing elegant, terroir-driven wines that reflect the distinctive character of Burgundy’s vineyards.
Half Baked at HiNote
Get ready for The Feel-Good Evening of the Month with a special screening of Half Baked at HiNote on November 24!
Doors open at 7:00 PM, and the movie starts around 8:00 PM.
Attendees can enjoy complimentary munchies, along with THC drinks and shots for purchase. Full alcoholic cocktails and a complete food menu will also be available throughout the night.
Colum Tyrrell
After beginning his career in his home country of Ireland, Colum Tyrrell moved to New York City and quickly became one of the fastest-rising comics in the scene, performing regularly at the world-famous Comedy Cellar and many other top clubs. In 2023 he made his American national television debut on The Tonight Show with Jimmy Fallon and is now a touring headliner. Performing across the United States almost every weekend, he has earned a reputation as a ferocious standup act not to be missed.
Saturday Wine Tastings at Unity Table: Wines for the Upcoming Holidays
Join local sommelier, Daniel McCurdy, for an educational wine experience and food pairing upstairs at Williams Hall’s Unity Table from 2pm to 4pm. Explore a selection of wines perfect for holiday dinners, festive gatherings, and celebrations with family and friends, accompanied by thoughtfully paired bites from Chef Martha Hubbard.
Sunday Wine Tastings at Unity Table: Wines for the Upcoming Holidays
Join local sommelier, Daniel McCurdy, for an educational wine experience and food pairing upstairs at Williams Hall’s Unity Table from 2pm to 4pm. Explore a selection of wines perfect for holiday dinners, festive gatherings, and celebrations with family and friends, accompanied by thoughtfully paired bites from Chef Martha Hubbard.
Unity Table Chef's Dinner: Fennel Friendly
Join Chef Martha Hubbard of Unity Table for a creative three-course dinner all about fennel. She’ll explore the ingredient in both savory and sweet dishes, showing just how versatile it can be.
Coast is Clear Music & Arts Festival
The Coast Is Clear Music & Arts Festival is back this December 4-6 with a weekend-long series of cultural events to celebrate the official end of Atlantic Hurricane Season. Held at venues throughout Bahama Village in Key West, the festival includes a mix of ticketed live-music shows as well as plenty of free music & events, including the Petronia Street Block Party which takes place all day (10am-10pm) on Saturday, December 5.
Bougie Afternoon Tea Party
Enjoy delicious finger sandwiches, petite quiches, scones, clotted cream & mini desserts at the beautifully decorated Hellings Curry Museum (home of the Key West Women's Club). Includes specialty cocktails, hot tea and champagne. All proceeds go to funding the KWWC Take Stock in Children Scholarship.
Florida Keys Seafood Festival
Join the Florida Keys Commercial Fishermen’s Association for the 21st Annual Florida Keys Seafood Festival, a two-day celebration of the Keys’ fishing heritage at Truman Waterfront Park in Key West.
Enjoy amazing fresh seafood, browse local vendors, and listen to live music all day long with beer and wine to go with it. Kids’ activities make it a fun outing for the whole family.
Unity Table Chef's Dinner: An Evening in Thailand
Join Chef Martha Hubbard at Williams Hall’s Unity Table for an intimate six-course journey through Thailand, featuring distinctive dishes and flavors rarely found in the United States. This exclusive culinary experience promises a memorable evening, with only a limited number of seats available.
Unity Table Chef's Dinner: Guest Chef Dave Fuhrman of Great Events
Guest Chef Dave Fuhrman returns to Unity Table, bringing decades of culinary experience and a passion for fresh, local flavors. As chef and owner of Great Events Catering, a well-known Key West catering company, Dave is recognized for his creative flavor profiles and unique presentations. Join him for another of his always-popular four-course Chef’s Dinners.
Stack & Lew's Fright Night Party
Get ready for a spooktacular Halloween night with Stack & Lew! Join us at General Horseplay for pumpkin carving, live entertainment, and a costume contest with a cash prize.
Hush Money
This fresh, fabulous new drag show is hosted by winner of Best in Drag at the 2026 Bubba Awards in Key West, Beatrix Dixie. HUSH MONEY dives headfirst into a deliciously naughty world of fame, fortune and temptation.
Expect brand-new material, iconic drag classics, killer looks, comedy, glamour, and unforgettable performances from some of the best drag talent Key West has to offer. One minute you’ll be laughing, the next you’ll be gagging—and you may leave knowing a few things you probably weren’t supposed to hear.
A Pirate Looks Back - Jimmy Buffett Tribute Show
Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume as the man himself in a show blending live music, storytelling, humor, and of course...Cheeseburgers! Enjoy a journey back in time to a place where artists and misfits lived the eclectic Bohemian dream, and our favorite "grandson of a sailor" roamed the land.
Part lunch theater, part tribute concert, and part educational adventure, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the songs, spirit, and the island where the legend began. This show is a MUST-SEE for all Buffett fans, music enthusiasts, or anyone looking for Key West’s most entertaining lunch experience.
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.
Yuck Show
Part of the new Family Fun Series, which is designed to bring engaging and exciting performances for audiences of all ages to the Key West community. This series features a diverse lineup of shows, carefully selected to entertain and inspire families. Featuring colorful large-scale spectacles, quirky comedy, and audience interaction, the Yuck Show is a joyful, visual celebration of science enjoyed by audiences of all ages.
Hocus Pocus at HiNote
Join us for a girly movie night under the spell of Hocus Pocus.
Pajama party. Cozy. Curated menu.
Snacks included.
Come as you are (in your pajamas, that is) for a night of cozy magic, good company, and a little Halloween nostalgia. See you there, witches! 🕯️🍂
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/Mangoes Restaurant-no need to go anywhere else. Bags of beads to toss to the crowd below! MC'd by John "Ma" Evans. Private entrance and restrooms.
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 24th, as Key West transforms into a vibrant playground. Enjoy your favorite wine, a local beer, or a delicious mimosa as you watch the parade go by. With its intimate setting and prime location, Vinos on Duval is the ideal spot to soak up the atmosphere and celebrate Fantasy Fest in style.
Space is limited, so arrive early to secure your spot.
Ticket includes a welcome Prosecco or sangria and light snacks.
Mangoes Fantasy Fest Parade Party
Join us a step above Duval Street for one of the most epic parties of the year! Mangoes Private Parade Party puts you right in the heart of the action with an elevated patio for prime parade viewing, incredible drink specials, air-conditioned indoor space, and a special parade-night dinner menu available for purchase.
STUDIO 319 - Party Like a Rockstar
For one night, 319 Duval goes full rockstar!
Dress as your favorite music icon, enter through our private gate, pass the velvet ropes, and step into Studio 319. Grab a cocktail, take your reserved seat in our courtyard, and watch the Fantasy Fest Parade in first-class style from the heart of historic Duval Street.
Your ticket includes reserved courtyard seating, a chef-prepared gourmet buffet, handcrafted signature cocktails, sparkling clean private restrooms, and an exclusive VIP celebration behind the gates of one of Key West’s most iconic historic homes.
New Orleans House Pool Party
Soaking Wet Pool Party / Parade day.
Come splash around in the pool or jacuzzi while listening to music to get you hyped with live DJ and pool games.
Join us 12 Noon until 5pm at New Orleans House! Clothing Optional.
Kinky Couples Party hosted by Rubberdoll!
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. Live DJ will be sure to get everyone in the mood for some serious playtime!
Bourbon St Pub's Afternoon Pool Party
Fantasy Fest 2026, Poolside Dance Party / Street Fair T Dance at the Bourbon St Pub Adult Complex.
Get your groove on while dancing and drinking at the Duval Street T Dance or Poolside at the Bourbon St Pub! Live DJs, Boys, Beads and Booze, Drag Queens, games and MORE! 12 noon until 5-ish.
Exposed
10PM-4AM - Event Open to All! The most risqué party of Fantasy Fest! Voyeur/Exhibition areas throughout! Play in the Poolside Foam Party!
Dance the night away w/DJ Gyvers/outdoor Laser Light show, Splash around in our Pool & Jacuzzi! Black Out & Black Light party inside, TheTazzle.com will be there adding some extra excitement with fun giveaways of OXJOK and more!
43rd Anniversary of the Headdress Ball 2026
This unforgettable evening of creativity, glamour, and entertainment will once again be hosted by legendary Key West entertainer Randy Roberts, with music by WEOW’s RudeGirl. Guests will experience an extraordinary showcase as twelve to fifteen contestants unveil their stunning Headdress creations, judged from the shoulders up, all competing for the coveted $5,000 grand prize. The evening will also feature performances by some of Key West’s most celebrated local talent, making this a true highlight of Fantasy Fest. Guests can enjoy full bar service, specialty wines, and the convenience of preordered food delivered directly to their tables.
6th Annual "Rock the Tatas"
Hank’s hair of the Dog Saloon presents the annual charity event, Rock the Tatas contest. Join us in the fight against Breast Cancer. Our energetic event will be hosted by Mr Happy Hour Key West and DJ EL Grace. Contest starts at 7pm at Hanks Hair of the Dog Saloon located at 409 Caroline St. First place price $500 along with a crown and a stash! With additional cash prices for second and third place. Contestants will be judge on charism, creativity and costume design
Desire Male Fetish Party
Fetish Party 10PM - 4AM.
Private Fetish party - For the Men, Fetish attire encouraged. Live DJ, Exhibition areas, Bring out the Gear!
Free clothes check w/ $30 door cover.
The Rocky Horror Picture Show
Get ready to do the Time Warp again!
The Tropic Cinema is turning up the decadence for a three-night extravaganza featuring The Rocky Horror Picture Show, running October 21 through 23 at 8:00 PM nightly.
Hosted by your favorite local cult leader, Landon, this isn't just a movie—it’s a full-blown, interactive fever dream where sitting quietly in your seat is strictly forbidden.
Fantasy Fest Spooky Trivia
Bring all you favorite guys and ghouls for a one-of-a-kind TRIVIA experience. This spooky Fantasy Fest trivia features all the fun decorations of a proper Halloween Party, 6 great rounds of Trivia, Creepy drink specials, and the BEST part of all... all players in costume receive 5 bonus points! Reservations are a must; tables will fill fast! 6pm Sharp! $25, including your first spooky drink!
Tops or Bottoms Underwear Party
Underwear party 10PM - 4AM.
Private Underwear party - For the Men, You must lose one or the other or both!
Free clothes check w/ $20 door cover.
Masquerade Monday Wine Dinner Presented by Bogle Wines
Step into an evening of mystery and elegance at our High-Society, Great Gatsby Roaring Twenties Era.
Masquerade Ball + Wine Tasting Dinner featuring Bogle Wines. Dress the part in your favorite mask and costumes and enjoy a night where fine wine, exquisite food and live music and entertainment comes together. Savor a multi-course dinner paired with wine, while the music sets the mood for a magical night of intrigue and celebration.
$185 includes dinner, wine, and gratuity. Cocktails will be charged on consumption.
A&B Lobster House - 700 Front St | Doors @ 6PM | Welcome drink @ 6:30PM | Dinner @ 7PM
Masks are REQUIRED, seats are limited
A Pirate Looks Back - Jimmy Buffett Tribute Show
Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume as the man himself in a show blending live music, storytelling, humor, and of course...Cheeseburgers! Enjoy a journey back in time to a place where artists and misfits lived the eclectic Bohemian dream, and our favorite "grandson of a sailor" roamed the land.
Part lunch theater, part tribute concert, and part educational adventure, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the songs, spirit, and the island where the legend began. This show is a MUST-SEE for all Buffett fans, music enthusiasts, or anyone looking for Key West’s most entertaining lunch experience.
Afterlife: the Awakening
Step into the forbidden garden of desire at Bourbon Street Pub. This one-night experience transforms the Garden into a realm of aerial burlesque performed over the pool, voyeur shower stations, and sensual performances that ignite every sense.
Guests will wander through seductive zones designed to tempt and tease, leading up to electrifying stage shows and free-flowing encounters that set the tone for the week ahead. This isn’t just a party — it’s the erotic heartbeat of Fantasy Fest.
Sip n Slay - Pop Art Zombie Edition w/ Beatrix Dixie
Ever wanted to learn to paint your face like a professional? Nows your chance! Voted Best In Drag in the 2026 Bubba Awards, Join Beatrix Dixie in her step by step, make up master class where she will demonstrate how to turn yourself into a pop art zombie just in time for the festivities! It's required to bring your own makeup and tools for the event! We will list recommendations for supplies to create a long lasting look and to fully execute this process! Let's have some fun!!!
Hush Money
This fresh, fabulous new drag show is hosted by winner of Best in Drag at the 2026 Bubba Awards in Key West, Beatrix Dixie. HUSH MONEY dives headfirst into a deliciously naughty world of fame, fortune and temptation.
Expect brand-new material, iconic drag classics, killer looks, comedy, glamour, and unforgettable performances from some of the best drag talent Key West has to offer. One minute you’ll be laughing, the next you’ll be gagging—and you may leave knowing a few things you probably weren’t supposed to hear.
2026 What I Did Fur Love Royal Coronation
Join the Florida Keys SPCA at the 2026 What I Did Fur Love Royal Coronation where we will celebrate all 4 candidates at the culmination of their 6 week fundraising campaign.
Kick off Fantasy Fest to see who becomes the King & Queen of Fantasy Fest 2026! This fabulous 2-hour stage show includes entertainment by local celebrities and the candidates themselves!
Tickets include reserved seatingand a 3-course plated dinner by Catered Affairs (vegan meal available upon request - please email Jennifer@fkspca.org to order in advance). Cash bar for all.
Barbie's Pink Pool Party for Breast Cancer Awareness
Wear your Best Barbie or Ken pink costumes and join The Marker Key West Harbor Resort along with a fun pool party that will also make you feel good! Along with great music by DJ Top Jimmy and DJ Maya, we'll have a Barbie or Ken costume contest, Barbie pink pools, Barbie pink drink specials by Empress Gin, pink food specials, and more – all to benefit Womankind Key West.
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.