Friday Night Cash Bingo
Get your daubers ready and join the fun every Friday night for an exciting evening of Cash Bingo! Whether you're a seasoned pro or a first-timer, there are cash payouts for every single game, so everyone has a chance to take home the prize.
Summer Studio Series: Performance & Dance Social #2
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.
Celebrate Juneteeth!
Join the community for a Free Community Event that is completely open to the public! Come together to honor freedom, culture, and community with an evening packed with live performances, music, and refreshments.
Acupuncture
Community Acupuncture is an accessible way to experience the healing benefits of acupuncture in a shared space. In this group setting, individuals receive personalized treatment while relaxing alongside others. Whether you’re seeking relief from stress, pain, or other health concerns, community acupuncture offers a peaceful, supportive environment to promote healing and well-being for everyone. Vitamin injections and ear tacks may also be available during these times.
FREE!
Monday Night Jazz Jam
Kick off your week with the vibrant sounds of live music at the Monday Night Jazz Jam! Happening every single Monday evening, this community event invites musicians, singers, and music enthusiasts alike to come together for a night of incredible improvisation and rhythm.
FREE!
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.
Larry Baeder's Jazz Trio
Get ready for an unforgettable evening of incredible music! Join us for a special performance by Larry Baeder’s Jazz Trio, featuring the legendary Terri White. Whether you're a lifelong jazz aficionado or just looking for a fantastic night out, this is a performance you won't want to miss. Spread the word, bring a friend, and come enjoy the smooth sounds and vibrant atmosphere!
FREE!
Friday Night Cash Bingo
Get your daubers ready and join the fun every Friday night for an exciting evening of Cash Bingo! Whether you're a seasoned pro or a first-timer, there are cash payouts for every single game, so everyone has a chance to take home the prize.
Live Music: The Shanty Hounds!
Get ready for a fantastic evening of live music with The Shanty Hounds! Mark your calendars and bring your friends out for a great night of tunes, community, and fun.
FREE!
Summer with the Symphony Chamber Music Featuring Piano Trios by Farrenc & Pejačević
South Florida Symphony’s popular chamber music series comes to Key West, bringing cool sounds to a sultry summer afternoon with an intimate, candlelit concert. Farrenc’s and Pejačević’s piano trios sparkle with undeniable charm -- as piano, violin, and cello mingle in a playful exchange of musical ingenuity. (Huifang Chen, violin; Claudio Jaffe, cello; and Catherine Lan, piano)
Enjoy a special post-concert meet-and-greet reception with the musicians, featuring a refreshing champagne spritzer and sweet treats — all part of the experience.
Monday Night Jazz Jam
Kick off your week with the vibrant sounds of live music at the Monday Night Jazz Jam! Happening every single Monday evening, this community event invites musicians, singers, and music enthusiasts alike to come together for a night of incredible improvisation and rhythm.
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!
Raiders of the Lost Ark
Mike’s favorite movie.
Adventure. Mystery. Nazis getting their faces melted. Few films have ever matched the pure movie magic of Raiders of the Lost Ark . Join us as Indiana Jones races around the globe in one of the greatest action films ever made.
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.
Friday Night Cash Bingo
Get your daubers ready and join the fun every Friday night for an exciting evening of Cash Bingo! Whether you're a seasoned pro or a first-timer, there are cash payouts for every single game, so everyone has a chance to take home the prize.
Monday Night Jazz Jam
Kick off your week with the vibrant sounds of live music at the Monday Night Jazz Jam! Happening every single Monday evening, this community event invites musicians, singers, and music enthusiasts alike to come together for a night of incredible improvisation and rhythm.
FREE!
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.
Friday Night Cash Bingo
Get your daubers ready and join the fun every Friday night for an exciting evening of Cash Bingo! Whether you're a seasoned pro or a first-timer, there are cash payouts for every single game, so everyone has a chance to take home the prize.
Summer Studio Series: Performance & Dance Social #3
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.
Monday Night Jazz Jam
Kick off your week with the vibrant sounds of live music at the Monday Night Jazz Jam! Happening every single Monday evening, this community event invites musicians, singers, and music enthusiasts alike to come together for a night of incredible improvisation and rhythm.
FREE!
Sideways & Special Wine Tasting
Tuesday, July 14 • Tasting 6:30 PM • Film 8 PM
Join sommelier Daniel McCurdy for a special wine tasting before the film exploring the wines of the central coast. No merlot will be served. Lite bites from Chef Martha.
A movie that launched a thousand wine clubs and nearly destroyed the reputation of merlot forever. Funny, moving, and proof that middle-aged existential crises can occasionally be entertaining.
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.
Friday Night Cash Bingo
Get your daubers ready and join the fun every Friday night for an exciting evening of Cash Bingo! Whether you're a seasoned pro or a first-timer, there are cash payouts for every single game, so everyone has a chance to take home the prize.
Monday Night Jazz Jam
Kick off your week with the vibrant sounds of live music at the Monday Night Jazz Jam! Happening every single Monday evening, this community event invites musicians, singers, and music enthusiasts alike to come together for a night of incredible improvisation and rhythm.
FREE!
Stop Making Sense at HiNote
Possibly the greatest concert film ever made.
David Byrne dances. The band gets bigger. The suit gets larger. The music gets louder. Somehow it all makes perfect sense.
Doors at 7. Film at 8ish.
Friday Night Cash Bingo
Get your daubers ready and join the fun every Friday night for an exciting evening of Cash Bingo! Whether you're a seasoned pro or a first-timer, there are cash payouts for every single game, so everyone has a chance to take home the prize.
Summer Studio Series: Performance & Dance Social #4
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.
Monday Night Jazz Jam
Kick off your week with the vibrant sounds of live music at the Monday Night Jazz Jam! Happening every single Monday evening, this community event invites musicians, singers, and music enthusiasts alike to come together for a night of incredible improvisation and rhythm.
FREE!
JAWS
You’re gonna need a bigger boat.
Steven Spielberg’s summer blockbuster classic returns to the big screen. Equal parts suspense, adventure, and pure movie craftsmanship, JAWS remains the gold standard for summer movie nights.
Friday Night Cash Bingo
Get your daubers ready and join the fun every Friday night for an exciting evening of Cash Bingo! Whether you're a seasoned pro or a first-timer, there are cash payouts for every single game, so everyone has a chance to take home the prize.
Lobsterfest Trivia
Get ready to test your knowledge at the Key West Lobsterfest, featuring an evening of Pub Style Trivia with a Lobster Twist. For $50 per person, attendees can enjoy the competitive atmosphere along with a fresh lobster roll and a drink included with their entry.
Summer Studio Series: Performance & Dance Social #5
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.
Cocktail at HiNote
Tom Cruise. A shaker. The 80s at peak 80s.
Cocktail is back on screen, and there is no more perfect place in Key West to watch it than High Note. Specialty cocktails, obviously. Flair bartending appreciation, mandatory. Your best 80s energy is welcome.
Doors at 7. Film at 8ish.
Tropical Heat
TROPICAL HEAT is Key West’s HOTTEST event for all gay, bi, queer, and trans brothers!
The temperature is not the only thing that will rise during Tropical Heat. The theme parties, pool parties, and adult-oriented entertainment promises to be HOT! August on the Island is always HOT, but during Tropical Heat it promises to be STEAMY! Five hot guys and fun days are the best way to experience Key West. Tropical Heat 2026 August 12th - 16th! Don't miss it!
With the V.I.P. band, you will receive entry or discounted entry to all parties & 5-day pass to Island House.
Wizard of Oz with Pink Floyd
Hosted by Brandon Beach.
One movie. One legendary album. Decades of people saying, “Okay, but hear me out…”
Whether you’re a true believer or convinced the whole thing is nonsense, it’s one of the weirdest and most entertaining movie experiences you’ll ever have.
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.
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.
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.
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.
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
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.
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.
Yin Yoga
Yin yoga is a slow-paced, meditative style of yoga where passive poses are held for a long duration, typically 3 to 5 minutes or longer. This practice targets deep connective tissues like ligaments, joints, and fascia, contrasting with more active styles that focus on muscles. The long holds encourage a state of stillness to increase flexibility, improve joint mobility, and foster a deeper mental and physical awareness.
FREE!
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.
Acupuncture
Community Acupuncture is an accessible way to experience the healing benefits of acupuncture in a shared space. In this group setting, individuals receive personalized treatment while relaxing alongside others. Whether you’re seeking relief from stress, pain, or other health concerns, community acupuncture offers a peaceful, supportive environment to promote healing and well-being for everyone. Vitamin injections and ear tacks may also be available during these times.
FREE!
Purple Rain at HiNote
Prince. Specialty cocktails. The best music movie ever made. What else do you need?
Purple Rain is coming to HiNote and honestly, this is exactly how Prince would have wanted you to watch it.
Doors at 7. Film at 8ish. Purple attire strongly encouraged.
Paint the Town Proud Pub Roll
Join us on the Old Town Trolley Tour for the "Paint the Town Proud Pub Roll", an exciting adventure outside Key West's historic and vibrant Gayborhood. This unique event celebrates the island's LGBTQ+ cultural heritage while you enjoy specially curated Pride-themed drinks at each stop. Be sure to dress in your favorite color of the rainbow to win best dressed! We'll kick off the tour at Bobby's Monkey Bar, where you can enjoy delicious breakfast bites and a welcome drink. A cash bar is also available for mimosas, Bloody Marys, or any other drinks you might want to have before the tour begins!
Summer Studio Series: Performance & Dance Social #1
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.
A Mojito Masterclass
Join us at Tropicado Mojito Bar at La Concha Hotel for an immersive, hands-on mojito experience in the heart of Key West!
Shake, “slap”, and sip your way through the art of crafting the perfect mojito as you explore Papa’s rum, fresh ingredients, and the vibrant spirit of Havana. This interactive class is a must-do for cocktail enthusiasts, curious beginners, and anyone looking to elevate their island 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.
Official Key West Pride Kick-off
Presented by the Key West Business Guild and Gay Key West, this year's Pride event carries the overarching theme of “Color the island: A Celebration of Identity Through Color & Creativity.” Join us for a vibrant kick-off to Pride 2026 as we transform the island into a living canvas of self-expression, artistry, and community. Color the Island is more than an event; it’s an immersive celebration of identity, where every hue tells a story, and every voice adds to the theme. The celebration features local DJ Mr. Enjoy, local vendors, delicious food, and unlimited drinks! All included with your entry! Come ready to color the island with pride!
Yin Yoga
Yin yoga is a slow-paced, meditative style of yoga where passive poses are held for a long duration, typically 3 to 5 minutes or longer. This practice targets deep connective tissues like ligaments, joints, and fascia, contrasting with more active styles that focus on muscles. The long holds encourage a state of stillness to increase flexibility, improve joint mobility, and foster a deeper mental and physical awareness.
FREE!
Rum Around the World
Experience worldly flavors and vibrant island vibes at the "Rum Around the World" event, hosted at Papa's Pilar Distillery in the heart of Key West. Taking place on May 30th, 2026, doors for this exclusive evening open at 6:00 PM. Guests will have the unique opportunity to sample a diverse selection of rums from various countries, proudly offered by the Foreign Liaison Officers' Association. Located at 201 Simonton Street, Key West, Florida, this gathering promises good company and a rich tasting experience at the home of the Hemingway Rum Company.
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.
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!
Yang Yoga
Yang yoga is the active, dynamic style of yoga that builds strength and stamina through flowing movements, unlike the passive, static poses of Yin yoga. It is characterized by rhythmic sequences that generate heat, such as those found in Vinyasa, Ashtanga, and Power Yoga, focusing on muscles and circulation to strengthen and lengthen them.
FREE!
Acupuncture
Community Acupuncture is an accessible way to experience the healing benefits of acupuncture in a shared space. In this group setting, individuals receive personalized treatment while relaxing alongside others. Whether you’re seeking relief from stress, pain, or other health concerns, community acupuncture offers a peaceful, supportive environment to promote healing and well-being for everyone. Vitamin injections and ear tacks may also be available during these times.
FREE!
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.
Sons and Daughters of Italy Key West Lodge 47th Birthday Party & Wine Tasting
Join the Sons and Daughters of Italy, Key West Lodge, for an evening of wine, music, and celebration as we mark our 47th anniversary on Wednesday, May 20, 2026. We invite you to Grand Vin Wine Bar at 1107 Duval Street from 5:30 PM to 7:30 PM for an Italian wine tasting paired with delicious antipasto and, of course, birthday cake.
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.
Yin Yoga
Yin yoga is a slow-paced, meditative style of yoga where passive poses are held for a long duration, typically 3 to 5 minutes or longer. This practice targets deep connective tissues like ligaments, joints, and fascia, contrasting with more active styles that focus on muscles. The long holds encourage a state of stillness to increase flexibility, improve joint mobility, and foster a deeper mental and physical awareness.
FREE!
Group Meditation Circle
Group meditation is the practice of meditating collectively with others in a physical space. Participants gather together to meditate simultaneously, cultivating a shared energy that enhances the overall experience. Classes typically consist of 20-30 minutes of active meditation, with space and time allowed for check-in and integration. This communal practice can take various forms including guided meditation, silent meditation, or meditation accompanied by music or chanting. The essence of group meditation lies in the synergy created, as individuals come together to explore mindfulness and elevate their consciousness.
FREE!
Casino Night MMXXVI
Join the Rotary Club of Key West on May 16, 2026, for Casino Night: Roaring ’20s Speakeasy! 🥂
Step back in time at the Beachside Resort for a night of blackjack, jazz, and specialty cocktails. All proceeds benefit local scholarships. 🎓 Dress your best for a chance to win prizes! Transport yourself back to the 1920s for a night of high-stakes fun and prohibition-style elegance! The Rotary Club of Key West invites you to our annual Casino Night gala. This year, we’re transforming the Beachside Resort into a secret Speakeasy where the jazz is hot, the drinks are cold, and the gaming is for a great cause.
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.
Acupuncture
Community Acupuncture is an accessible way to experience the healing benefits of acupuncture in a shared space. In this group setting, individuals receive personalized treatment while relaxing alongside others. Whether you’re seeking relief from stress, pain, or other health concerns, community acupuncture offers a peaceful, supportive environment to promote healing and well-being for everyone. Vitamin injections and ear tacks may also be available during these times.
FREE!
Key West Playwrights Festival
Join us for an engaging evening of original short plays at Williams Hall, showcasing fresh voices and new works from a diverse group of playwrights. This intimate festival highlights the power of live performance, where compelling storytelling and imaginative perspectives take center stage. Each piece offers a unique glimpse into the creativity of today’s writers, brought to life in a setting that invites audiences to connect closely with the work.
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.
Yin Yoga
Yin yoga is a slow-paced, meditative style of yoga where passive poses are held for a long duration, typically 3 to 5 minutes or longer. This practice targets deep connective tissues like ligaments, joints, and fascia, contrasting with more active styles that focus on muscles. The long holds encourage a state of stillness to increase flexibility, improve joint mobility, and foster a deeper mental and physical awareness.
FREE!
Group Meditation Circle
Group meditation is the practice of meditating collectively with others in a physical space. Participants gather together to meditate simultaneously, cultivating a shared energy that enhances the overall experience. Classes typically consist of 20-30 minutes of active meditation, with space and time allowed for check-in and integration. This communal practice can take various forms including guided meditation, silent meditation, or meditation accompanied by music or chanting. The essence of group meditation lies in the synergy created, as individuals come together to explore mindfulness and elevate their consciousness.
FREE!
One Night of Queen
One Night of Queen is a spectacular live concert that perfectly recreates the look, sound, pomp and showmanship of the greatest rock band of all time: Queen.
Gary Mullen & The Works bring the spirit and passion of rock icon Freddie Mercury to life on stage. As Brian May, original member of Queen, states, "(Gary Mullen has) more than a likeness." Hailed as the world's premiere Queen tribute band, they have received rave reviews from audiences worldwide. Fans of Queen will revel in this note-for-note experience of mega-hits like "Bohemian Rhapsody," "We Are the Champions," "Killer Queen" and many more. They will rock you and are guaranteed to blow your mind—the show does go on!
Songwriters Soul Brunch: Sunday Songs
Join us to celebrate the end of Songwriters Festival with a Southern-style brunch at Williams Hall's Unity Table before the "Sunday Songs: Music & Mimosas"
Brunch includes exclusive balcony seating for the show.