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.
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.
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.
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.
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.
"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.
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.
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!
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!
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.
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.
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!
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.
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.
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!
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!
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!
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.
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.
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.
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.
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.
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.
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.
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.
Wizard of Oz with Pink Floyd
One movie. One legendary album. Decades of people saying, “Okay, but hear me out…”
Experience one of the most talked-about film and music pairings of all time!
For decades, audiences have claimed that The Wizard of Oz and Pink Floyd’s iconic album, The Dark Side of the Moon, sync together in surprising and often uncanny ways. Coincidence? Happy accident? Pure imagination? The debate continues—and now you can experience it for yourself.
Eeland Stribling
Eeland Stribling is your aunty’s favorite stand-up comedian.
Eeland is a regular at The Comedy Fort, Comedy Works and Denver Improv. He recently won the 2023 New Faces competition at Comedy Works! He also regularly tours in Boston, Chicago, LA, Austin and venues across the country. He has traveled across the world teaching about fly fishing and telling jokes everywhere he can.
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.
Rum Masterclass: An Educational Journey Through Venezuelan & Jamaican Rums
Join us for an exclusive masterclass diving deep into the rich histories, distinct production styles, and complex flavor profiles of world-class rums. Featuring two iconic brands—Diplomático Rum and Worthy Park Estate—this immersive event offers a side-by-side exploration of Venezuelan and Jamaican rum-making traditions.
True Crimes of Key West
Join us for our second installment of Drink & Think's local lecture series at Rick's brand new Old Sailor Bar! Yvonne Jefferson, owner of iWitness: True Crime Tours, will take you through some of Key West's most notorious, and lesser known, true crime stories.
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.
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.
Lobster Roll Eating Contest
Official Lobsterfest Event!
Lobster roll eating contest… $30 to enter. Comes with 1 lobster roll – the fastest to finish it completely, wins!
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.
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.
Mark Chalifoux
Mark Chalifoux is a nationally touring stand-up comedian. He was most recently featured on Nate Bargatze's Nateland and has told jokes on Dry Bar Comedy and FOX. His comedy album, “Think Fast”, opened at #2 on Apple Music, has been streamed more than 5 million times on Pandora, and is played regularly on SiriusXM. His Dry Bar Comedy special has been seen millions of times across social media and he was the longtime writer behind The Dad, one of the most popular comedy accounts on social media.
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. Not Hungry? For $25 per person, attendees can enjoy the competitive atmosphere along with a drink only included with their entry.
The Spain Tables
Join Salty Chef Catering for an unforgettable evening of flavor, culture, and giving back at The Spain Tables — a Salty Chef Experience benefiting our local Marine Corps unit. Set at The Studios of Key West, this charity event brings together Spanish-inspired cuisine, live music, cocktails, and great people, all in support of the men and women who serve. A portion of proceeds goes directly to a local Marine Corps unit, helping support their mission, families, and community outreach.
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.
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.
Drink & Think: Inside the Mind of an Expert
This is the inaugural presentation in our newly formed lecture series featuring local experts across different industries. The topic is AI: The Good, The Bad, and The Ugly.
Presented by Marlene Kolodziej, CTO and IT Director of the Monroe County School District and Computer Science Adjunct Professor at College of the Florida Keys.
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.