Jimmy Dunn
Jimmy Dunn is a stand-up comedian and actor from Boston, who currently plays “Moose” on the Paramount+ reboot of the iconic sitcom FRASIER. He can be heard most Tuesdays on The Greg And The Morning Buzz radio network. He got his start in "show business" telling jokes in a bar in Gloucester, Massachusetts, where he was paid in beer and fried clams. Since then, he’s gone on to perform at some of the world’s most prestigious comedy events, including the Late Show with David Letterman, CONAN, Montreal’s International Just For Laughs Comedy Festival, and Denis Leary’s Comic’s Come Home in Boston. Jimmy’s first major television role was as Sean McCarthy on the CBS sitcom, THE MCCARTHYS. He’s also written on several television projects, including two episodes of LOUDERMILK that he co-wrote with Academy Award winner Peter Farrelly.
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 College of the Florida Keys 60th Anniversary Celebration
Toast to six decades of educational excellence at The College of the Florida Keys’ milestone 60th Anniversary Celebration, featuring fine dining, cocktails, historical exhibit, live music by Bay Kings Band, and dancing in honor of the College's rich legacy and continued commitment to student success.
Stories & Supper With Lucy Burdette
Join us for a special literary evening featuring Lucy Burdette, USA Today bestselling author of the beloved Key West Food Critic mystery series. Enjoy a live reading of one of Lucy’s short stories by local creative and actress Erin McKenna, followed by dinner prepared by Chef Martha and conversation celebrating storytelling and community.
Keys Choral Arts: "Songs for the People"
Presented at the Key West United Methodist Church, the spring concert, "Songs for the People" will in part, honor the many women composers and artists of our time, featuring new compositions and arrangements by women. This will also feature a set of American Spirituals, with guest artist, dramatic soprano Dr. Amy Yekel.
A reception will follow the concert.
Soul City dysFUNKshunals
Get ready to experience the perfect blend of rhythm and swing as SOUL CITY dysfunkshunals brings "Motown with a Jazz Attitude" to the stage. Join Clayton Lopez, Larry Smith, Christine Cordone, and Skipper Krippitz for an evening of soulful melodies and sophisticated arrangements that celebrate the best of both genres. With surprise guest appearances often including local favorites like Mina Lopez and Journey Blue Heaven, every performance offers a unique and high-energy musical journey.
Jess Wach Jazz Cabaret
Get ready for an immersive musical experience that goes beyond the stage. Jess Wachs presents her Jazz Cabaret, a series of soulful performances where, as the event tagline promises, "You’re not watching music. You’re inside it."
Hosted at the Key West Cultural Center & Veterans Museum, these Saturday night sessions blend classic jazz vibes with the intimate atmosphere of a cabaret.
FREE!
And Tell Sad Stories of the Death of Queens
Little-known short plays by Tennessee Williams that boldly explore sexuality, identity, and longing. Presented in partnership with the Tennessee Williams Festival at Williams Hall. Directed by Dominic Paolillo. Cast: Kitty Clements, Cassidy Timms, Aramis Ikatu, Phillip Cole, Todd Glenn, Jim Speake, Trey Forsyth, Diane May, Chris Massicotte, Kathy Russ, Mariah Woessner, Davis Stack, Barbara Mundy.
Venue: Williams Hall, 729 Fleming St.
A Night with Tequila Ocho at HiNote
Join us for an exclusive, guided journey through the world of premium agave spirits. Hosted at HiNote—the intimate cocktail lounge located upstairs at General Horseplay—this event offers a deep dive into the craft and heritage of Tequila Ocho.
Your evening begins with a refreshing welcome cocktail followed by a curated tasting of four specialty pours. From 7:00 PM to 9:00 PM, guests will enjoy an educational session led by industry experts, exploring the unique "single estate" philosophy that defines Tequila Ocho. After the formal tasting concludes, the bar will remain open until late, allowing you to settle in and enjoy the atmosphere of one of Key West's most hidden gems.
Houston Ballet II
Houston Ballet II (HBII) is the second company of Houston Ballet, America’s fifth largest ballet company. Comprised of a stellar array of ballet students from around the world, HBII members perform a diverse range of dance works such as excerpts from the great classics including The Sleeping Beauty, Swan Lake, and The Nutcracker to contemporary works by Houston Ballet Artistic Director, Stanton Welch AM.
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!
Jessimae Peluso
Jessimae Peluso is a stand-up comedian, writer, performer, TV and podcast host whose work blends raw comedy with emotional depth. Known for her breakout role on MTV’s Girl Code and hosting Netflix’s Tattoo Redo and Surviving Paradise, Jessimae has spent nearly two decades turning personal pain into punchlines.
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.
Habitat for Humanity's Tropical Gala
Habitat for Humanity of Key West and Lower Florida Keys provides affordable homeownership opportunities to low-income working families and critical home repairs to our community’s vulnerable elderly population. We are dedicated to empowerment, not entitlement, and bringing people together to build homes, communities, and hope. As a locally supported nonprofit the work we do is only made possible through support from the community. Proceeds from Habitat’s 2025 sold-out gala helped provide 9 families with affordable, safe homes to call their own, 5 senior household with critical home repairs allowing them to age in place, and 27 families with affordable rentals.
Our 2026 event will feature a delicious dinner, creative libations, and inspiring program, games, auctions, dancing and an all-around memorable evening. We invite you to attend, sponsor, and be recognized as we come together again in 2026 for a fun evening to change lives and build a better 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.
Anne McKee Artists Fund Performance featuring Belle Jampol
Influenced by soul, jazz, and folk, Belle brings a unique blend of musical flavors to her performances.
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!
Puppy Pals, Live!
The Puppy Pals Comedic Stunt Dog Show is a hilarious presentation for the whole family and the dog lover in all of us, the spectacle stars mostly rescued dogs.
Steve Rannazzisi
For over 13 years, from the stage to the silver screen, Steve Rannazzisi has made audiences laugh. Currently, Rannazzisi stars and writes alongside Katie Aselton, Mark Duplass, Nick Kroll, Jonathan Lajoie, and Paul Scheer on the critically acclaimed FX Network comedy series, The League, which is produced by Jeff and Jackie Schaffer.
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.
"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.
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!
Gastor Almonte
Gastor Almonte is a Dominican-American stand-up comedian, writer, and podcaster based in New York City. Raised in Brooklyn, he’s known for his warm, thoughtful delivery and deeply personal storytelling—blending culture and identity into comedy that’s both smart and emotionally grounded. Gastor has been featured on Comedy Central and NBC, and he performs regularly at top clubs and theaters across the country. His work has also appeared at major comedy festivals and across digital platforms, where he’s earned a reputation as a comedian’s comedian—respected for his writing, honesty, and point of view.
The Shark is Broken
Written by Ian Shaw and Joseph Nixon
The Hit of the Edinburgh Fringe 2019
Three actors. One small boat. Alcohol flows. Egos clash. A cinematic shoot that will make history -- assuming someone can figure out how to fix that blasted shark. This 'bitingly funny' play is the true story of behind the scenes of the movie JAWS. Starring: Trey Forsyth, Mathias Maloff, and Ray West.
Tickets: $45-$65 (does not include fees)
Jillian Todd: A Celebration of Joni Mitchell
This special evening promises to captivate audiences with soul-stirring renditions of Mitchell's most beloved songs, including 'A Case of You' and 'Big Yellow Taxi'. Renowned singer and guitarist Jillian Todd will headline the event, bringing her unique talent and heartfelt interpretations to the stage. As one of the most influential and celebrated singer-songwriters of all time, Joni Mitchell's music has touched the hearts of millions around the world. Her talents have left an indelible mark on the music industry and continue to inspire generations of artists.
Amos Gill
Amos Gill is one of Australia’s hottest comedians, now making waves internationally as a touring headliner across the USA, UK, and Australia. Known for his sharp humor and quick wit, Amos first gained attention as a beloved Adelaide radio host on Amos, Cat & Angus. After leaving radio in 2018, he quickly became a comic to watch, earning accolades such as runner-up in triple j’s RAW Comedy competition and hosting the Melbourne International Comedy Festival’s prestigious Comedy Zone.
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.
4th Annual FRLA Monroe R.O.S.E Awards
The ROSE (Recognition of Service Excellence) Awards recognizes Monroe County front line hospitality employees who demonstrate excellent customer service. These industry champions showcase the region’s commitment to creating an extraordinary visitor experience.
Sponsorship opportunities available.
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Conch Crawl Pub Stroll
Celebrate the spirited independence of the Conch Republic with the ultimate Old Town stroll! As part of the 44th Anniversary celebration, the annual Conch Crawl invites you to experience the best of Key West’s legendary bar scene while supporting a great cause.
The Lineup
Your ticket grants you access to nine of Old Town’s most famous establishments: 801 Bourbon Bar, Mango’s, Hank’s Hair of the Dog, Kaya’s Backyard Bar, Doc’s on Duval, Irish Kevin’s Bar, Rick’s Downstairs Bar, Salty Frog’s Bar & Grill - Plus, stay for the official After Party!
Movies Under the Stars: Shrek
Join us for a magical, family-friendly evening under the stars with a screening of the beloved 2001 animated hit Shrek!
Follow a grumpy but lovable ogre on a hilarious quest to rescue a feisty princess with the help of a talking donkey and a whole lot of fairy tale twists.
Conch Republic Military Muster
Stand at ease and prepare for a sovereign celebration like no other!
As part of the 44th Annual Conch Republic Independence Celebration, we invite you to the official Military Muster. This is your exclusive opportunity to rub elbows with the "High Command" from all seven prestigious branches of our military forces—all decked out in their finest full regalia. In true Conch Republic fashion, we fight our battles with humor, heart, and a side of conch fritters.
Whether you are a long-time citizen or a newly arrived "alien," come share in the community spirit as we defend our borders from "Key to Shining Key."
Admission to this community event is $20 plus a potluck donation to share with your fellow patriots.
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!
Conch-tail Party: Dinner and Sunset Toast
Get ready to shell-ebrate 44 years of independence at the Conch-Tail Party, Dinner & Sunset Toast!
Join the fun on April 21 from 6:00 PM to 9:00 PM at the legendary Sunset Pier for an evening of harborside dining and island tradition. You’ll be mingling with Admirals, Generals, and local legends while enjoying live tunes from Reggae Lou and Sir CW Colt.
Between the official 21 Conch Shell Salute and the sunset toast, it’s the most festive way to honor the Republic.
Grab your tickets for $50 before the price jumps to $60 after April 10.
Tony V
In 1986 Tony V was named “Funniest Person in Massachusetts” by Showtime television. He followed this achievement with several performances on HBO, the Arts and Entertainment Network, Comedy Central and MTV. From 1987 through 1992 Tony V became the “spokesperson” for American Tourister Luggage. Remember the suit case smashing gorilla? It was Tony that gave the ape it’s distinct voice and temperament. Touring extensively in and out of his high tech forty-five thousand dollar yak hair gorilla suit, both Tony and his alter ego had many interesting adventures. If you get a chance ask Tony about a meeting between The Gorilla, Spuds MacKenzie and Ronald McDonald. You won’t believe your mind.
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.
Sunshine at the Sandbar with a Sunset
Kick Off Songwriters Week on the Water with Erica "Sunshine" Lee! ☀️🎤
Get ready for the ultimate private concert experience! We’re hitting the waves for 6 hours of sun, music, and good vibes. Catch a live 1-hour performance by Erica "Sunshine" Lee while we cruise.
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!
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!
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.
Long Live Lambada!
Dust off your dancing shoes and get ready for a theatrical heatwave because the “Forbidden Dance” is making a scorching comeback! From April 28 to April 30, 2026, the Tennessee Williams Theatre transforms into a pulse-pounding portal to Brazil as the Key West International Dance Company presents the high-octane spectacle, Long Live Lambada! This isn’t your typical night at the ballet; it’s a "crazy, sexy," and wildly immersive celebration with world-class choreography.
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.
Doug Benson
Doug Benson is known for his popular podcasts (Doug Loves Movies and Getting Doug With High), his films (Super High Me, The Greatest Movie Ever Rolled, Chronic-Con: Episode 420), appearances on TV shows like @midnight, The Trailer Park Boys and You're The Worst, and for presiding over The High Court as ‘Judge Doug’ on Comedy Central.
One Night of Queen
One Night of Queen is a touring 2-hour stage show, paying tribute to the stage theatrics and music of Queen.
Eddie Gossling
From festivals to late-night television appearances, Eddie Gossling has been holding it down in the comedy industry for over 20 years. Known for his sharp wit and engaging stage presence, he has built a reputation and crafted a style that's equal parts edgy and endearing. Arguably his most notable accomplishment outside of stand up is his involvement with Comedy Central's "Tosh.0," where he served as a writer and co-executive producer for 12 seasons. Gossling's contributions to the show helped shape its comedic style and earned him recognition within the industry. In addition to his work behind the camera, Gossling has also made appearances on popular late-night shows like "Jimmy Kimmel Live" and starred in his own Comedy Central special.
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.
MicroPARTY Live Show
Big news! Electric Blue Yonder’s MicroPARTY LIVE is coming back to Key West at Tropic Cinema‘s Carper Theater for two very special shows Saturday, May 9th at 3:00pm & 5:30pm!
This is an all ages, family friendly show of music, dancing, puppetry, and immersive multimedia based on the music of Electric Blue Yonder’s 2025 National Parenting Product Award winning Children’s album, MicroPARTY.
MicroPARTY Live Show
Big news! Electric Blue Yonder’s MicroPARTY LIVE is coming back to Key West at Tropic Cinema‘s Carper Theater for two very special shows Saturday, May 9th at 3:00pm & 5:30pm!
This is an all ages, family friendly show of music, dancing, puppetry, and immersive multimedia based on the music of Electric Blue Yonder’s 2025 National Parenting Product Award winning Children’s album, MicroPARTY.
Sean Patton
Sean Patton is a comedian based in New York, by way of New Orleans. He began doing stand-up in the Crescent City and has since performed in comedy clubs and festivals across the world, including The Melbourne International Comedy Festival (2011, 2018), The Glasgow Comedy fest (2016), the Dublin Comedy fest (2017), and The Edinburgh Fringe (2017, 2019). Other festivals appearances include SXSW (2016, 2017, 2018, 2022), The Moontower comedy festival (2012, 2013, 2014, 2019), Just for Laughs Chicago (2013), Just for Laughs Toronto (2013) and Just for Laughs Montreal (2008, 2010, 2012, 2016, 2018).
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.
Dancapalooza: Be Our Guest
Step into the magic of Dancapalooza: Be Our Guest, Island Groove Dance Studio’s 2026 annual showcase. Inspired by timeless wonder, storytelling, and the joy of performance, this year’s production will transport audiences into a world of imagination through music, movement, and unforgettable stage moments. With performances by youth and adult dancers from across the Middle and Lower Keys, the showcase will feature a dynamic mix of Hip Hop, Ballet, Tap, Jazz, Lyrical, Acro Dance, and more. Be Our Guest is a celebration of creativity, confidence, and community, and a chance for local dancers to share their passion and hard work on stage in a truly special way.
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.
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.
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.
John Caparulo
A comedian known for his sharp wit, unique delivery, and brilliant affinity for cuss words, John Caparulo is a seasoned comic whose dry, no-nonsense Midwestern sensibility endears him to audience members of all kinds. He began his comedy career performing in clubs in Cleveland and Pittsburgh in the late ‘90s before coming to Hollywood to hone his skills on stage and work the door at the legendary Comedy Store. Caparulo's breakout performance at Montreal's Just for Laughs in 2003 led to spots on The Late Late Show with Craig Kilborn, The Tonight Show with Jay Leno, Jimmy Kimmel Live, and he appeared over 150 times as a panelist on Chelsea Handler’s popular E! show Chelsea Lately.
Dan Soder
Dan Soder is a New York City-based comedian who’s best known as ‘Mafee’ on the hit Showtime Billions series. His HBO Special “Son of a Gary” debuted December 7th, 2019. He has a Half Hour Special on Netflix’s “The Standups”. His first hour-long stand-up special, Not Special premiered in 2016 on Comedy Central.
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.
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!
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!
Key West Brewfest Grand Tasting Event 2026
Key West BrewFest is an island wide festival hosted by the Key West Sunrise Rotary of the Conch Republic and the Southernmost Beach Resort. This is a 100% nonprofit, charitable event, to raise money for local student’s scholarships.
Science, Technology and Operational Advances in Meteorology Since the 1935 Labor Day Hurricane
Jonathan Rizzo's presentation takes a compelling look back at the catastrophic 1935 Labor Day Hurricane, one of the most powerful storms to strike the United States and Florida Keys. Rizzo will guide the audience through the severe limitations of meteorologists of that era faced in predicting and communicating its impact. The presentation will also examine the growing role of social science in hazardous weather messaging and how forecasters communicate risk in ways that motivate action.
Terri White, Larry Baeder & Friends
Experience a night of world-class music and soul in the heart of Key West! Every Thursday, Broadway legend Terri White teams up with the versatile Larry Baeder for a high-energy residency that blends the best of American music. Renowned for her powerhouse roles on Broadway in Ain’t Misbehavin’ and Chicago, Terri White brings her unmatched stage presence to the stage alongside Larry Baeder and a rotating cast of new guest musicians each week.
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.
Dealing with Tough Customers and Colleagues: Practical Skills for the Workplace and Beyond
Learn tools you can apply to your life immediately to:
Calm people down when they are angry
Resolve conflict quickly and effectively
Turn unhappy customers around
Deal with negativity without it getting you down
Say no effectively…and much more!
Elisa Levy is a speaker and author, who has travelled the world teaching conflict resolution, leadership and customer service. Her clients run the gamut from major hotel chains, fortune 500 companies, the United Nations and nonprofit organizations.
Ladies Night with Larry Smith
Ladies Night with Larry Smith is a weekly musical showcase hosted at the Key West Cultural Center & Veterans Museum. This event is open to the public and features a rotating lineup of talented female vocalists throughout the month of March.
March 25 Line-up:
Camille Russo Toler: A beloved local favorite proficient in performing soul, jazz, and rock music.
Jamie Olwell: A 44-year resident of Key West who sings with passion in her own unique, sweet style.
FREE!
Jazz at Lincoln Center presents Great American Crooners
Soak in the sounds of the velvety melodies and smoky rhythms of quintessential crooners such as Frank Sinatra, Tony Bennett, and Bobby Darin when the golden age of jazz returns with Great American Crooners!
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.
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!
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.
Cheers to 10 Years!
It’s a Celebration! The Fringe Board invites you to join us on March 23rd as we celebrate ten years with Rebecca Tomlinson as Fringe’s Managing Artistic Director. We’re celebrating the people, the shows, and the direction that has led Fringe Theater through its unprecedented growth. Join us for music, food, and memories!
Your ticket price includes the Ericson Holt Band, Food stations and hors d'oeuvres, Open Bar. We’ve memories to share and new memories to make!
Sponsored by William & Pattye Monroe, Blake Hunter & Murphy Davis, Dennis Beaver & Bert Whitt, Neal Ruchman & Melissa Jean McDaniel, The Gardens Hotel, Billy Cartledge & Jim Hall, and Janet & Charlie Bengel.
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!
Paradise Big Band
Under the baton of Joe Dallas Jr, the band remains a truly "local" organization consisting of professional and semi-professional musicians from the Lower Keys and primarily Key West. In the interest of enhancing both solo and ensemble performances, the band regularly features outstanding guest artists from New England, New York City and Pittsburgh.
Movies Under the Stars: 10 Things I hate About You
Join us for a fun-filled evening under the stars with a screening of 10 Things I Hate About You!
A high-school boy, Cameron, cannot date Bianca until her anti-social older sister, Kat, has a boyfriend. So, Cameron pays a mysterious boy, Patrick, to charm Kat.
Sean Finnerty
From Longford, Ireland, Sean Finnerty decided to move stateside where a series of mature decisions that he failed to make led him to stand-up comedy. Recently he was rewarded for his efforts as he became the first ever Irish comedian to perform on the Tonight Show with Jimmy Fallon. Spending his first number of years in comedy based out of Orlando, Sean was selected for Comedy Central’s Up Next competition, made his television debut as co-host of Season 9 of Fireball Run on Amazon Prime. He has also performed at several festivals including Laugh Your Asheville Off, Edinburgh Fringe, and Electric Picnic, along with making it to the semi finals of the nationwide talent search Stand Up NBC. A keen eye for detail Sean has also developed a reputation as a Roaster and is currently the number 1 ranked roast comic in New York City.
Crimes of the Heart
Beth Henley’s beloved Pulitzer Prize winning script. Three eccentric sisters. A forgotten birthday, a failed career, an attempted murder. Funny. Messy. Filled with southern comfort. Featuring Martha Hooten-Hattingh, Sarah-Hunter Wald, Abigail Emerson, Samantha Laskey, Dan Dempsey, and Dominic Paolillo.
Tickets: $45-$65 (does not include fees)
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!
Soft Opening: Key West Cultural Center & Veterans Museum
Join us for an exclusive first look at the Key West Cultural Center & Veterans Museum! We are opening our doors for a special Soft Opening event to share our vision with the community and gather your valuable feedback. Located at the historic William Weech American Legion Post 168, this evening is a celebration of local history, service, and the arts.
Soul City dysFUNKshunals
Get ready to experience the perfect blend of rhythm and swing as SOUL CITY dysfunkshunals brings "Motown with a Jazz Attitude" to the stage. Join Clayton Lopez, Larry Smith, Christine Cordone, and Skipper Krippitz for an evening of soulful melodies and sophisticated arrangements that celebrate the best of both genres. With surprise guest appearances often including local favorites like Mina Lopez and Journey Blue Heaven, every performance offers a unique and high-energy musical journey.
Hemingway in a Funny Way
Comedy Key West is happy to be bringing back the first show paying tribute to the funny side of the life and works of Ernest Hemingway. A few blocks down the street from the famed Hemingway House, where he lived and wrote for nine years, and around the corner from his legendary watering hole Sloppy Joe’s, comedian James Scott Patterson takes us on an hourlong tour of Hemingway’s childhood, writing career, adventuring, and, of course, drinking days. The humor ranges from the tragic-comic (it is Ernest Hemingway after all) to the witty, wild, and difficult to believe. The show is a happy hour celebration from 5:30 to 6:30 including a complimentary glass of Hemingway’s favorite wine (Valpolicella) with your ticket.
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.
Terri White, Larry Baeder & Friends
Experience a night of world-class music and soul in the heart of Key West! Every Thursday, Broadway legend Terri White teams up with the versatile Larry Baeder for a high-energy residency that blends the best of American music. Renowned for her powerhouse roles on Broadway in Ain’t Misbehavin’ and Chicago, Terri White brings her unmatched stage presence to the stage alongside Larry Baeder and a rotating cast of new guest musicians each week.
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.
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.
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!
Ladies Night with Larry Smith
Ladies Night with Larry Smith is a weekly musical showcase hosted at the Key West Cultural Center & Veterans Museum. This event is open to the public and features a rotating lineup of talented female vocalists throughout the month of March.
March 18 Line-up:
Adrienne Z: A unique singer/songwriter who is well-known and respected across the Keys.
Leanne Collins Hettinger: A former island singer/songwriter and current Michigan resident making a welcomed return to Key West.
FREE!
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!
Speaker Series: Christopher Castellani
Christopher Castellani is the author of six books, most recently the novel Last Seen. His previous book is Leading Men, a novel about Tennessee Williams and Frank Merlo, for which he received Fellowships from the Guggenheim Foundation, and MacDowell. Leading Men is currently being adapted for film.
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!
Bad Teachers w/ Cory Michaelis and friends
Teachers (and former students) of Key West! Celebrate your long weekend with the comedy of a teacher who couldn't cut it - Cory Michaelis. After 12 years of teaching high school, Mr. Michaelis decided drunken hecklers were easier to deal with than students. Come see two class periods worth of mostly teacher/student material relatable to anyone who has ever been in a classroom. Non-teachers and teachers alike will love this show and some admin. will be on the show to keep us all in line. Irreverent (but PG-13-ish) comedy, shot specials, prizes, and a Kahoot!
Carr-Petrova Duo
Described as "ravishing" (Strad), "enlightened" (BBC), "explosive" (Virginia Gazette), and "irresistibly elegant" (Diario de Leon), violist Molly Carr and pianist Anna Petrova are rapidly compiling a remarkable list of accolades in recognition of their fiery musical expression, refined artistry, and relentless entrepreneurial dedication to social initiatives.