A Pirate Looks Back - Jimmy Buffett Tribute Show
Jun
15
to Jun 19

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.

View Event →
Yin Yoga
Jun
16

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!

View Event →
Tom Arnold
Jun
18
to Jun 20

Tom Arnold

Tom Arnold is an actor, writer, and comedian with a career spanning over forty years, appearing in hundreds of hours of television and over one hundred and fifty films. He is best known for roles on Roseanne, True Lies, Nine Months, The Stupids, Carpool, McHale’s Navy, Big Bully, Austin Powers, and Soul Plane. He has hosted Saturday Night Live four times, has had three HBO specials, and starred in four sitcoms. Tom has won a Golden Globe, a Humanitas Award, and a Peabody Award, and has appeared on the Jimmy Kimmel Show, Howard Stern, and was a co-host on “The Best Damn Sports Show Period.”

View Event →
Summer Studio Series: Performance & Dance Social #2
Jun
19
to Jun 21

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.

View Event →
A Pirate Looks Back - Jimmy Buffett Tribute Show
Jun
22
to Jun 26

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.

View Event →
Acupuncture
Jun
22

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!

View Event →
Patrick Garrity
Jun
25
to Jun 27

Patrick Garrity

After starting comedy at an early age, Patrick Garrity has developed into a veteran of the road. He doesn't just work the road he lives on it. Since 2010 he's been traveling the country nonstop on a never-ending tour with no actual residence. His versatility and raw talent make him one of the most unique stand ups touring today.

View Event →
Summer with the Symphony Chamber Music Featuring Piano Trios by Farrenc & Pejačević
Jun
28

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.

View Event →
A Pirate Looks Back - Jimmy Buffett Tribute Show
Jun
29
to Jul 3

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.

View Event →
Raiders of the Lost Ark
Jun
30

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.

View Event →
Ricky Cruz
Jul
1
to Jul 3

Ricky Cruz

With a comedy career spanning over 20 years Ricky Cruz is a nationally seasoned talent. Working alongside the greats of comedy, touring with the late Ralphie May, and appearing on comedy specials for HBO, NBC, and Sirius Xm radio. He’s all grown up and sharing the twisted true-life tales that have shaped him and his point of view along the way.

View Event →
A Pirate Looks Back - Jimmy Buffett Tribute Show
Jul
6
to Jul 10

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.

View Event →
Vibrator Races for Charity!
Jul
9

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.

View Event →
Summer Studio Series: Performance & Dance Social #3
Jul
10
to Jul 12

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.

View Event →
A Pirate Looks Back - Jimmy Buffett Tribute Show
Jul
13
to Jul 17

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.

View Event →
Clouds Over the Sunshine Inn
Jul
14
to Jul 18

Clouds Over the Sunshine Inn

Summer Fringe presents Ben Harrison’s musical rom-com, CLOUDS OVER THE SUNSHINE INN. Will corporate greed get its just desserts when it stands in the way of true love? How sweet it is!  

View Event →
Sideways & Special Wine Tasting
Jul
14

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.

View Event →
A Pirate Looks Back - Jimmy Buffett Tribute Show
Jul
20
to Jul 24

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.

View Event →
Stop Making Sense at HiNote
Jul
21

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. 

View Event →
Summer Studio Series: Performance & Dance Social #4
Jul
24
to Jul 26

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.

View Event →
A Pirate Looks Back - Jimmy Buffett Tribute Show
Jul
27
to Jul 31

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.

View Event →
JAWS
Jul
28

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.

View Event →
A Pirate Looks Back - Jimmy Buffett Tribute Show
Aug
3
to Aug 7

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.

View Event →
Lobsterfest Trivia
Aug
5

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.

View Event →
Summer Studio Series: Performance & Dance Social #5
Aug
7
to Aug 9

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.

View Event →
Cocktail at HiNote
Aug
11

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. 

View Event →
Tropical Heat
Aug
12
to Aug 16

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.

View Event →
Wizard of Oz with Pink Floyd
Aug
18

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.

View Event →
Summer Studio Series: Performance & Dance Social #6
Aug
21
to Aug 23

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.

View Event →
The Big Lebowski
Aug
27

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.

View Event →
Summer Studio Series: Performance & Dance Social #7
Aug
28
to Aug 30

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.

View Event →
Roger Bartlett & Emily Randle
Sep
6

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. 

View Event →
Key West oktoBREWfest
Oct
3

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

View Event →
43rd Anniversary of the Headdress Ball 2026
Oct
22

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.

View Event →

When Worlds Collide, a reading
Jun
11

When Worlds Collide, a reading

Summer Fringe presents a reading of short Key West plays by Chris Moore. We featured Chris’s first play, END OF THE ROAD, during Summer Fringe 2024 and produced a fully staged production of his PERSONAL EFFECTS earlier this season. Now we’re presenting a reading of his latest stories that take a fresh and quirky look at our island home.

View Event →
Key West Comedy Competition
Jun
10
to Jun 13

Key West Comedy Competition

Comedy is art. And art is subject to opinion. Which makes it impossible to judge fairly. But we’re doing it anyway…

Florida comics bring their best bits to our stage, and the audience helps pick who should win the night and the cash!  Wednesday’s show will also feature an interactive first look at “The Key West Gameshow”, a fantastically fun night with your favorite game shows, coming soon to Comedy Key West.

View Event →
Kyle Kinane & Matt Braunger
Jun
8

Kyle Kinane & Matt Braunger

Kyle Kinane is a comedian from Addison, Illinois. According to Wikipedia, he is a notable person from that town. Other notable residents of Addison have been the boxer Leon Spinks and a woman who wrote poetry about Beanie Babies. Matt Braunger is a comedian, actor, writer, etc. You’ve probably seen him in something, but you maybe don’t know what (Netflix’ Big Dumb Animal, Marvel’s Agent Carter, Mad TV).

View Event →
Acupuncture
Jun
8

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!

View Event →
A Pirate Looks Back - Jimmy Buffett Tribute Show
Jun
8
to Jun 12

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.

View Event →
Purple Rain at HiNote
Jun
7

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.

View Event →
Paint the Town Proud Pub Roll
Jun
6

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!

View Event →
Billy Anderson
Jun
5
to Jun 6

Billy Anderson

Billy Anderson is a standup comedian who can be heard on Audible’s “Sounds Like America” hosted by Jackie Kashian and seen on season 3 of the syndicated program “Laughs” on Fox television. In 2018 he released his first live comedy special titled “America’s Sweetheart” through The Harmon Brother’s Dry Bar Comedy series on Amazon Prime. You can see Billy both at the Hollywood Improv and touring internationally as the host of the hit comedy showcase The Gateway Show.

View Event →
Summer Studio Series: Performance & Dance Social #1
Jun
5
to Jun 7

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.

View Event →
A Mojito Masterclass
Jun
5

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.

View Event →
Gateway Show with Billy Anderson
Jun
4
to Jun 7

Gateway Show with Billy Anderson

The Gateway Show has a simple premise: Stand-up comedians take to the stage sober to tell their BEST jokes, then they go to an undisclosed location to get WAY too high, only to come back to the stage and ATTEMPT to tell more jokes while completely stoned.

View Event →
Official Key West Pride Kick-off
Jun
3

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!

View Event →
Yin Yoga
Jun
2

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!

View Event →
A Pirate Looks Back - Jimmy Buffett Tribute Show
Jun
2
to Jun 5

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.

View Event →
Dan Soder
Jun
1
to Jun 2

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.

View Event →
Rum Around the World
May
30

Rum Around the World

  • Heminway Rum Company, Papa's Pilar Distillery (map)
  • Google Calendar ICS

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.

View Event →
John Caparulo
May
28
to May 31

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.

View Event →
The Ladies in the Orange Grove, a reading
May
28

The Ladies in the Orange Grove, a reading

Summer Fringe presents a reading of The Ladies in the Orange Grove by David Schmitt. Sibling rivalry is taken to the extreme in this family saga of wealth and betrayal. Written by David Schmitt who moved to Marathon at age five. He graduated San Pablo school, Marathon High, and the University of Miami, then studied in New York. He has written and workshopped 24 full length plays and 800 one acts . 

View Event →
Yang Yoga
May
26

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!

View Event →
Acupuncture
May
25

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!

View Event →
A Pirate Looks Back - Jimmy Buffett Tribute Show
May
25
to May 29

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.

View Event →
An Evening of Storytelling & Comedy with Stormy Daniels
May
22
to May 23

An Evening of Storytelling & Comedy with Stormy Daniels

An evening of candid, comedic storytelling - followed by a live Q&A with the audience.

From life, to career, to scandal - it’s everything you want to know…and some things you may wish you didn’t. Whether you know her from television (SNL, VH1’s The Surreal Life, Host of OUTtv’s For the Love of DILFS), from magazines (Vogue, Vanity Fair, Rolling Stone), from the Peacock documentary Stormy, from movies (that can’t be mentioned here), or from the headlines - Stormy Daniels is now bringing her talents to the comedy stage. Stormy’s set is packed with hilarious stories from her time in adult entertainment, her personal life as a wife and mother… and of course, politics and scandal. Never one to shy away from the bold truth, every show ends with a live Q&A.

View Event →