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.
Reverend Raven and the Chain Smokin' Altar Boys
This Fringe Theater fundraiser is back by popular demand! These guys lit up the Armory last time they were in town (and sold out fast). Reverend Raven is as authentic as blues gets: original music in a classic blues style. You’ll want to get on that dance floor — we guarantee! This fundraiser includes open bar, buffet style food, incredible music, and all your Fringe friends!
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.
Fighting for Laughs, Too
Join us for Fighting For Laughs, Too — a night of powerhouse comedy featuring Sam Norton, Preston Gitlin, and headliner “The Reverend” Bob Levy, hosted by local veteran and comedian Petey Rancel. Building on last year’s sold-out success, this event delivers big laughs for an important cause.
All proceeds benefit AHERO, a 501(c)(3) organization dedicated to preventing Veteran and First Responder suicide through fellowship, outdoor adventures, and community support.
Your $50 general admission ticket directly helps fund AHERO trips here in Key West — creating healing connections and life-changing experiences for our nation’s heroes. Come laugh, support, and make a difference!
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.
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.
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 Love Party: a new play by Chantal Pavageaux
This Valentine’s day, you are invited to THE LOVE PARTY.
Step inside of a weird wonderful world full of storytelling, surprises, games and good times. Your hostess Meme “spills the tea” and shares a UNIQLY* Key West Love Story: a journey through personal hell in paradise, only to find love and self-acceptance at the end of the road — Mile Zero! Local audiences will recognize familiar locations and characters in this witty experimental play by local writer/director Chantal Pavageaux.
*UNIQLY stands for:
Untitled Neurodivergent Illustrated Queer Love storY
SOMO Roots
Southernmost Beach Resort and Reggae Lou invite you to SoMo Roots, an afternoon of live music and island vibes taking place on Sunday, February 15, 2026. The festivities kick off at 1:00 PM.
The event features a dynamic lineup of live performances by Reggae Lou & The Kind Budz and Channel 3. While guests enjoy the beach party atmosphere, the event also serves as a fundraiser for the S.O.S. Foundation.
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.
Diamonds are a Girls Best Friend
On Saturday, March 7, the Key West Woman’s Club will host its annual fundraiser Diamonds are a Girls Best Friend!
Enjoy an open bar, fully catered dinner, lively music by Skipper Kripitz & friends, and dancing while you shine in your diamonds!
The Italian American Dream with Analisa and John
Experience a truly authentic and unforgettable performance by Nashville’s own Analisa and John Gallo. This evening supports the local charities of the Sons and Daughters of Italy Key West Lodge.
Schedule: Dinner at 5:30 PM | Show starts at 6:45 PM
Admission: $50 (Includes dinner & one glass of wine)
"The Italian American Dream" show honors the story of the Italian immigrants of the early 1900s. It is a show for everyone, and highlights the themes of culture, family, sacrifice, and faith!
Mocktails & Manuscripts
The doors of the Hemingway Home will swing open for an unforgettable event Thursday, March 19th, 2026. Top mocktail creators will gather to mix, mingle, and compete for the coveted title of “Master Mixologist 2026”. The food pairing highlights the key skills of pairing food to enhance the mocktail experience.
Vintners Dinner
The iconic Vintners Dinner returns in 2026! “The ART of Tasting” is a chef-curated food and wine experience—an elegant evening of fine wines, delicious cuisine, and heartfelt community connection in beautiful, historic Williams Hall. Guests will enjoy a thoughtfully crafted multi-course tasting menu by Chefs John Corea and David Fuhrman, perfectly paired with exceptional wines presented by Pacific Southern Wine Company and Republic National Distributing Company. Erin McKenna hosts the evening of live music, Fine Wine & Cuisine, as we raise a glass to AH Monroe's four decades of compassion, innovation, and impact in the Keys.
Join us for an artful evening of wine, cuisine, and community connection!
Taste of Key West
Join us for one of Key West’s most anticipated foodie traditions! 🌴🍷
Taste of Key West returns for its 31st Annual Celebration, bringing together the island’s top restaurants, vintners, and beverage partners for an unforgettable open-air evening at Truman Waterfront.
"Endless Summer" Fundraiser with Howard Livingston & friends
Get ready to escape to the islands for a great cause at the "Endless Summer" Fundraiser with Howard Livingston & friends! This special event is more than just a concert; it's an unforgettable evening of high-energy "Trop Rock" music featuring Key West's own Howard Livingston & The Mile Marker 24 Band.
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.
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!!
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.
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.
Musical Benefit for Jamaica
MC Bill Hoebee.
Presentation by The United Cajun Navy.
Musical Director Larry Baeder,
Musicians:
Mike Dennis, Rolando Rojas, David Feder, Toko Irie, Larry Smith, Joe Dallas, Skipper Kripitz, Claire Sawyer Caplan, Peter Diamond Ilacqua, Christine Cordone Smith, Camille Russo Toler, Maj Johnson, Larry Baeder, Bubba Lownotes, Ben Harrison, Terri White, Massai, Tim Marshall Curtis, CW Colt.
Food provided by Yahman Jamaican Restaurant.
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.
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.
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.
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!
Time to Talk Turkey!
Join us at The Key West Cooking Show for two special Thanksgiving-themed classes that bring holiday traditions to life—island style!
✨ Learn hands-on recipes and techniques to elevate your holiday table.
🍽️ From the perfect turkey to creative sides and desserts, we’ll show you how to add both classic and modern twists to your feast.
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.
Thanksgiving Trivia
Do you have what it takes to be the smartest trivia team on stock island? Looking for a fun new holiday tradition? Bring your team to this one-of-a-kind holiday trivia & storytelling event! Family friendly! Everyone is welcome.
Details:
Teams of 6 or less. (2-6 players) Cost per team/table is $120. (100% of all money raised is used for the CFK HIGH SCHOOL students!)
$120 includes:
5 Rounds of Trivia plus a bonus round. Approx time should be about 1.5 hours.
A prize valuing at least $50 will be awarded after each round.
The 1st place winning team will receive a prize valued at over $300.
All tables will have light bites and non-alcoholic beverages served by our students.
Any other questions about our trivia fundraiser please contact Amy Andrade @ aandrade2010@live.com.
Time to Talk Turkey!
Join us at The Key West Cooking Show for two special Thanksgiving-themed classes that bring holiday traditions to life—island style!
✨ Learn hands-on recipes and techniques to elevate your holiday table.
🍽️ From the perfect turkey to creative sides and desserts, we’ll show you how to add both classic and modern twists to your feast.
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.
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.
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.
Nightcaps & Nightgowns
A Moonlight Pajama Party Parade Viewing Experience
One night. One view. One unforgettable pajama party.
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
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 and Empress Gin, along with a fun pool party that will also make you feel good! Along with great music by DJ Top Jimmy, we’ll have a Barbie or Ken costume contest, Barbie pink pools, Photo booth, Barbie pink drink specials, pink food specials, and more – all to benefit Womankind Key West… $20 donation – 4-7PM
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.
Cooking with Salt and Pepa
A flavorful fundraiser for Floyd “Pepa” Jenkins, candidate for Fantasy Fest King 2025, benefiting the Florida Keys SPCA 🐾
👨🍳 Featuring:
Chef Joey Bove (“Salt”)
Floyd Jenkins (“Pepa”)
Resident Chef Karl from the Key West Cooking School
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.
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.
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.