Landry
Landry is best recognized for his likable hair, sprouting from charismatic follicles. He is a Canadian born interracial love child whose hybrid existence when mixed with a little dysfunction, makes for a fantastic recipe of comedy goulash. He is the winner of both the Boston Comedy Festival and the World Series of Comedy but none of that matters so long as his mom thinks he's funny. With a smile that lights up a room and a personality to match, there is no telling what great things this young performer will achieve.
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.
Aqua Idol at the Legion
Starting Tuesday, September 8th join us for the Royal AQUA IDOL season! Every Tuesday, September 8th - October 13th, our group of singers will battle it out through song to become the winner of Aqua Idol for their King or Queen candidate to benefit the animals of the FKSPCA!
You can help your singer of choice and their King or Queen candidate win by donating dollars to their buckets and all proceeds will directly benefit animals! If you're looking for a fun event for a fantastic cause look no further! We look forward to seeing you there!
FREE!
Transformational Breathwork
Transformational breathwork is a practice that uses conscious breathing to move stagnant energy, integrate emotional and physical experiences, and facilitate healing and personal growth. This guided session helps you release tension, reset your nervous system, and reconnect with yourself.
FREE!
Grilled Cheese & Beer Pairing
Paired with brews from FL Keys Brewing, enjoy 4 different gourmet grilled cheese sandwiches, sure to please the palate - all while testing your team's knowledge with Pub Style Trivia!
Limited Space, Reservations Required!
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.
Key of Bones: Curse of the Ghost Pirate
Join the cast, filmmakers, and special guests for the official Key West premiere of Key of Bones: Curse of the Ghost Pirate, filmed entirely on location throughout Key West.
Key West oktoBREWfest
The main tasting event takes place on Saturday, October 3rd from 3-8pm. Expect over 60 beer vendors, more than 225 types of beers, live entertainment, and a guaranteed great time! Plus the Southernmost Beach Café will be open with beer hall food specials and cocktails for those who want to change it up!
VIP tickets: early 3pmadmission to beat the crowd, comes with a commemorative poster, special stainless steel VIP mug, and a Bavarian themed buffet - $125
GA tickets: $50 (5-8pm)
Designated Driver: includes admission, soft drinks and a coupon good for 1 food item - $20
Aqua Idol at the Legion
Starting Tuesday, September 8th join us for the Royal AQUA IDOL season! Every Tuesday, September 8th - October 13th, our group of singers will battle it out through song to become the winner of Aqua Idol for their King or Queen candidate to benefit the animals of the FKSPCA!
You can help your singer of choice and their King or Queen candidate win by donating dollars to their buckets and all proceeds will directly benefit animals! If you're looking for a fun event for a fantastic cause look no further! We look forward to seeing you there!
FREE!
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.
Italian Night at the Movie: Road to the Lemon Grove
The “Italian Night at the Movies” series kicks off on Wednesday, Oct. 7, with “Road to the Lemon Grove” starring Burt Young, Rossella Brescia and Nick Mancuso. Released in 2018, the comedy/romance film is in English and takes place in America and Sicily. A deceased Sicilian father has one last outrageous mission in store for his son, to spread his ashes in the lemon groves of Sicily, reunite two feuding families, while discovering the heart and soul of who he really is.
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.
Ghost Stories from the Gardens
Just in time for Halloween, join Island Tales for a creepy garden ghost tour.
This will be an enthralling evening filled with ghost tales and spooky legends led by 5-star rated tour guide Amy Andrade. Learn about haunted lighthouses, murder, betrayal, diseases, natural disasters, and ghosts that haunt the Florida Keys.
All proceeds will benefit the CFK Academy students.
Ghost Stories from the Gardens
Just in time for Halloween, join Island Tales for a creepy garden ghost tour.
This will be an enthralling evening filled with ghost tales and spooky legends led by 5-star rated tour guide Amy Andrade. Learn about haunted lighthouses, murder, betrayal, diseases, natural disasters, and ghosts that haunt the Florida Keys.
All proceeds will benefit the CFK Academy students.
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.
Dock & Dine Peruvian Sunset Dinner
🌅 Dock & Dine aboard the Free Spirit Yacht! 🛥️🍷
Experience an unforgettable Key West evening with Salty Chef Catering & Chef Juan Cuadra aboard the Free Spirit Yacht at Perry Marina.
Aqua Idol at the Legion
Starting Tuesday, September 8th join us for the Royal AQUA IDOL season! Every Tuesday, September 8th - October 13th, our group of singers will battle it out through song to become the winner of Aqua Idol for their King or Queen candidate to benefit the animals of the FKSPCA!
You can help your singer of choice and their King or Queen candidate win by donating dollars to their buckets and all proceeds will directly benefit animals! If you're looking for a fun event for a fantastic cause look no further! We look forward to seeing you there!
FREE!
A Taste of Peru with a Twist of Key West at Sazon Chapin
Join Salty Chef LLC and Sazón Chapín Guatemalan Restaurant on Wednesday, October 14 at 6:00 PM for "A Taste of Peru," a four-course drink pairing dinner. Chef Juan Cuadra—"the people chef"—presents a culinary journey honoring Peru’s history, vibrant traditions, and coastal flavors.
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.
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.
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.
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.
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.
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.
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
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.
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!
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.
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.
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
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.
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!
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.
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!
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.
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.
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.
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.
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.
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.
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! 🕯️🍂
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.
Appreciation Reception
The Key West Woman's Club invites you and your guest to the Museum Community Appreciation Reception, a special evening celebrating Key West’s vibrant museum community.
All museum staff, docents, tour guides, volunteers, and concierges are welcomed to attend and enjoy appetizers, an open bar, and time to mix and mingle. Attendees are encouraged to wear their organization's name badge, bring rack cards, and take the opportunity to meet colleagues while sharing details about upcoming events.
Free!
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.
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.
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.
Aqua Idol at the Legion
Starting Tuesday, September 8th join us for the Royal AQUA IDOL season! Every Tuesday, September 8th - October 13th, our group of singers will battle it out through song to become the winner of Aqua Idol for their King or Queen candidate to benefit the animals of the FKSPCA!
You can help your singer of choice and their King or Queen candidate win by donating dollars to their buckets and all proceeds will directly benefit animals! If you're looking for a fun event for a fantastic cause look no further! We look forward to seeing you there!
FREE!
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.
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.
Aaron Berg
Aaron Berg is a fixture on the NYC comedy scene, he is undeniably hilarious and packs the maximum amount of laughs per minute possible. No two sets are ever the same. Aaron was just cast in Uwe Boll’s new feature film The First Shift, which bolsters his acting resume to well over 50 projects including cult classic feature films like The Boondock Saints 2, Detroit Rock City, The Kitchen opposite Melissa McCarthy and Saturday Night Live’s The Ladies Man.
Aqua Idol at the Legion
Starting Tuesday, September 8th join us for the Royal AQUA IDOL season! Every Tuesday, September 8th - October 13th, our group of singers will battle it out through song to become the winner of Aqua Idol for their King or Queen candidate to benefit the animals of the FKSPCA!
You can help your singer of choice and their King or Queen candidate win by donating dollars to their buckets and all proceeds will directly benefit animals! If you're looking for a fun event for a fantastic cause look no further! We look forward to seeing you there!
FREE!
Tom Dustin
Edgy, original, and hilarious is the consensus of his comedy. Bostonian Tom Dustin is the only American to ever win the $25,000 Yuk Yuk's Great Canadian Laugh-off. He was so hilarious that the contest was closed to all future American contestants (USA! USA! USA!) He was also the winner of the Sam Adams Comedy Festival (Beer! Beer! Beer!) He's done Comedy Central, The Comedy Channel (Canada), local & national radio, podcasts, festivals, and roasts.
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.
Aqua Idol at the Legion
Starting Tuesday, September 8th join us for the Royal AQUA IDOL season! Every Tuesday, September 8th - October 13th, our group of singers will battle it out through song to become the winner of Aqua Idol for their King or Queen candidate to benefit the animals of the FKSPCA!
You can help your singer of choice and their King or Queen candidate win by donating dollars to their buckets and all proceeds will directly benefit animals! If you're looking for a fun event for a fantastic cause look no further! We look forward to seeing you there!
FREE!
Roger Bartlett & Emily Randle
Often referred to as "Coral Reefer #1," Roger Bartlett was Jimmy Buffett's first guitar player and was the foundation of the Coral Reefer Band. Roger joined Jimmy on the hit "Come Monday," and returned to help in the production of the album Volcano.
"You CAN Sit With Us" Drag Brunch, Benefiting Womenfest 2026
Wrap up an unforgettable Womenfest at our fabulous all-welcome Closing Drag Brunch, hosted by Hugh Janus! Enjoy spectacular drag performances, a special performance by our Queen Mother, Claire Brummell, delicious food, and nonstop laughter as some of Key West's most talented entertainers take the stage throughout the afternoon. Indulge in an abundant brunch buffet including flan and Key lime pie.
Annual Womenfest 80’s Prom and Afterparty
Dust off your shoulder pads, tease up your hair, and get ready to dance the night away at the Annual Womenfest ’80s Prom! This year’s celebration shines a spotlight on the Lost Women in Music, honoring the groundbreaking female artists whose voices, style, and influence helped define one of the most unforgettable decades in music. Come dressed in your favorite ’80s-inspired attire; whether you’re channeling an iconic music legend, rocking classic prom fashion, or creating your own totally rad look. Dance to the biggest hits of the decade, strike a pose for prom-worthy photos, and celebrate the women who made the ’80s soundtrack unforgettable. Costumes are NOT required, so grab your date, your friends, or come solo and make new ones as we relive the magic of prom, Womenfest style.
Lost Women, Found Art Gallery Trolley Tour
Celebrate the creativity and impact of women in the arts on this inspiring trolley tour of Key West’s women-owned and women-managed galleries. In honor of this year’s Lost Women in the Arts theme, you’ll visit a curated selection of local galleries, meet the artists and gallery owners behind them, and discover the stories, talent, and vision that continue to shape Key West’s vibrant arts community. Each gallery stop includes a complimentary beverage, giving you the chance to sip, socialize, and enjoy each unique space while learning about the featured artists and their work. Whether you’re an avid art collector or simply looking for a fun afternoon exploring Key West’s creative scene, this tour offers an engaging and memorable Womenfest experience.
Maddie Rean in Concert
Raised in the rural heart of South Carolina, Maddie Rean brings a little bit of rock, a whole lot of country grit, and a voice you won’t soon forget. Rooted in classic and Southern rock, country, blues, and a touch of rap, Maddie has created a sound all her own—bold, soulful, rebellious, and unmistakably Southern.
Maddie first caught national attention when her original song “Whiskey and Women” exploded on social media, earning more than 700,000 views and helping grow her following to more than 90,000 fans. Since then, she has taken her infectious live energy to stages across the East Coast and Midwest, sharing bills with artists including Morgan Wade, Riley Green, Parmalee, Lauren Alaina, Lonestar, Edwin McCain, David Nail, Ashland Craft, and more.
Dave Landau
Getting his start in Detroit at the Second City’s Conservatory, Dave Landau has become one of the most in-demand headliners working today. Dave’s laid-back demeanor and dark style of comedy landed him on Comedy Central’s “This is Not Happening,” and he is a regular panelist on Fox shows such as “Fox Across America,” “Who Can Forget?,” and “Kennedy.” He was also a finalist on season 8 of “Last Comic Standing” on NBC.
6th Annual Cornhole Competition
Get ready for a little friendly competition at the Annual Corn Hole Tournament & Indoor Games! Whether you’re a seasoned cornhole champion or just looking to have some fun, this event is the perfect opportunity to enjoy some spirited competition with fellow Womenfest attendees. In addition to the cornhole tournament, a variety of indoor games will keep the fun going for everyone. Grab a partner, make some new friends, and join us for an afternoon of games, camaraderie, and plenty of Womenfest fun!
How Money Works
Take control of your financial future—without the complicated jargon. Join financial consultant Teo Masters for How Money Works, an engaging, easy-to-understand conversation about saving, investing, getting out of debt, planning for retirement, protecting your income, and discovering your Financial Independence Number (FIN). Whether you’re just getting started or want to make smarter moves with the money you already have, you’ll leave with practical knowledge you can put to work right away. Come curious, leave empowered—and take the first step toward making your money work for you.
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.
The Key West Game Show
Key West Game Show!
Interactive game show just like your on TV with FABULOUS PRIZES hosted weekly at Comedy Club Key West!
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.
Best of Key West Jazz Concert Series
Best of Key West Jazz Concert Series
Featuring Key West Jazz All Stars & More: Larry Baeder, Joe Dallas, Terri White, Jeff Dalton & Mark Rose
Doors Always Open at 6:00
Dinner Always Available from Olive's Mediterranean Cafe
FREE Parking Available at 201 Truman Avenue
Suggested Donation: Fundraiser Proceeds Benefit William Weech American Legion Post 168 and the Key West Cultural Center & Veterans Museum (501.c.3)
FREE!
Summer Studio Series: Performance & Dance Social #7
Experience a night where the performance is only the beginning. The Key West International Dance Company invites you to an evening that blurs the line between the stage and the audience, starting with a professional showcase in Act I. You’ll witness a stunning display of world-class choreography before the lights come up for Act II, transforming the floor into a dance social where everyone is welcome to join the company and move to the beat.
General admission is free, and VIP table seating can be reserved in advance.
The Big Lebowski
The Dude abides. And tonight, he abides at Mary Ellen’s.
The Big Lebowski gets better every time you see it, and even better with a cold drink and a room full of people who already know every line. White Russians will be served.
Jenny Zigrino
With the sweetness of the midwest and the sharp edge of the east coast, Jenny Zigrino brings a powerful comedic performance to any stage. She combines hilarious anecdotes and sharp, witty observations with a cheeky style that challenges social norms and what it means to be human. Her brutal honesty and undeniable charm create a compelling comedic experience you won’t forget.
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.
Summer Studio Series: Performance & Dance Social #6
Experience a night where the performance is only the beginning. The Key West International Dance Company invites you to an evening that blurs the line between the stage and the audience, starting with a professional showcase in Act I. You’ll witness a stunning display of world-class choreography before the lights come up for Act II, transforming the floor into a dance social where everyone is welcome to join the company and move to the beat.
General admission is free, and VIP table seating can be reserved in advance.
Jeff Shaw
Jeff Shaw is an accomplished stand-up comedian and published writer whose two Dry Bar Comedy specials have garnered over 10 million online views and have streamed on both Peacock and Roku. Jeff has also competed on “America’s Got Talent,” is a regular on SiriusXM Radio, has been a guest on the nationally syndicated “The Bob & Tom Show” radio program, and has appeared on “Comics Unleashed with Byron Allen” on CBS.
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.
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.