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.

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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!

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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 . 

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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.

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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.

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A Pirate Looks Back - Jimmy Buffett Tribute Show
Jun
1
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.

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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.

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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!

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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!

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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.

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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.

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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.

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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.

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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!

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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.

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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.

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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!

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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).

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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.

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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!

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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.”

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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.

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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.

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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!

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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.

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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.

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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.

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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.

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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.

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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.

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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!  

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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. 

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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

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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!

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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.

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A Pirate Looks Back - Jimmy Buffett Tribute Show
May
21
to May 23

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.

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Tom Dustin
May
20
to May 21

Tom Dustin

Bostonian Tom Dustin is the funniest guy you’ve probably never heard of. He was the only American to ever win the $25,000 Yuk Yuk's Great Canadian Laugh-off, (resulting in future contests being closed to American comics) USA! USA! USA!  He was also the winner of the Sam Adams Comedy Festival. Beer! Beer! Beer!  He's done Comedy Central, The Comedy Channel (Canada), local & national radio, podcasts, festivals, and roasts.

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Sons and Daughters of Italy Key West Lodge 47th Birthday Party & Wine Tasting
May
20

Sons and Daughters of Italy Key West Lodge 47th Birthday Party & Wine Tasting

Join the Sons and Daughters of Italy, Key West Lodge, for an evening of wine, music, and celebration as we mark our 47th anniversary on Wednesday, May 20, 2026. We invite you to Grand Vin Wine Bar at 1107 Duval Street from 5:30 PM to 7:30 PM for an Italian wine tasting paired with delicious antipasto and, of course, birthday cake.

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Swing Dance Night with the Paradise Swing Band
May
19

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.

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Yin Yoga
May
19

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!

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Group Meditation Circle
May
18

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!

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Dancapalooza: Be Our Guest
May
17

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.

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CoffeeMill Dance Studio: DanceWorks 23!
May
16
to May 17

CoffeeMill Dance Studio: DanceWorks 23!

The CoffeeMill Dance Studio Celebrates 43 years of dance in Key West and proudly presents their annual Spring Dance Concert at the Tennessee Williams Theatre featuring a dance adaptation of Aladdin & The Legend Of The Lamp PLUS a fusion of many different dance styles including Ballet, Modern, Contemporary, Jazz, HipHop, Tap, Aerial Arts, Bellydance & Special Guest Artists!

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Casino Night MMXXVI
May
16

Casino Night MMXXVI

Join the Rotary Club of Key West on May 16, 2026, for Casino Night: Roaring ’20s Speakeasy! 🥂

Step back in time at the Beachside Resort for a night of blackjack, jazz, and specialty cocktails. All proceeds benefit local scholarships. 🎓 Dress your best for a chance to win prizes! Transport yourself back to the 1920s for a night of high-stakes fun and prohibition-style elegance! The Rotary Club of Key West invites you to our annual Casino Night gala. This year, we’re transforming the Beachside Resort into a secret Speakeasy where the jazz is hot, the drinks are cold, and the gaming is for a great cause.

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Walk with a Doc: Gut Check – What’s Normal and What’s Not
May
16

Walk with a Doc: Gut Check – What’s Normal and What’s Not

Take a step toward better health at our next Walk with a Doc event!
This month, we are focusing on digestive wellness with a special presentation and community walk designed to educate, exercise, and empower.
Join guest speaker Michael P. Klitenick, MD FACS, for an informative talk titled "Gut Check: What's Normal and What's Not." Dr. Klitenick will walk through common digestive issues, highlighting what symptoms to watch for and providing guidance on when it is time to seek professional care.

FREE!

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A Pirate Looks Back - Jimmy Buffett Tribute Show
May
14
to May 16

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.

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Wyatt Cote
May
13
to May 16

Wyatt Cote

Wyatt Cote dropped out of college one year shy of graduation to pursue a career in comedy and has since become one of the top competitive comics in the country with five contest wins to his credit including the 2021 World Series of Comedy. He was the runner up in the 46th annual San Francisco Comedy Competition and now tours the country performing full time. His stand up has appeared on Laughs on Fox and ABC news.

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Sean Patton
May
11
to May 12

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).

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Acupuncture
May
11

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!

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Threads of Love: A Mother’s Legacy through Dance
May
10

Threads of Love: A Mother’s Legacy through Dance

This year’s performance is a special tribute to the life of Mrs. Annie. More than just Mrs. Lynly’s mother, she was a "dance mom" to every student who walked through our doors. This Mother’s Day, we honor her legacy through movement, featuring dancers as young as two years old. Join us for a beautiful showcase of talent across ballet, tap, jazz, hip hop, and lyrical dance.

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MicroPARTY Live Show
May
9

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

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MicroPARTY Live Show
May
9

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

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Key West Playwrights Festival
May
7
to May 8

Key West Playwrights Festival

Join us for an engaging evening of original short plays at Williams Hall, showcasing fresh voices and new works from a diverse group of playwrights. This intimate festival highlights the power of live performance, where compelling storytelling and imaginative perspectives take center stage. Each piece offers a unique glimpse into the creativity of today’s writers, brought to life in a setting that invites audiences to connect closely with the work.

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A Pirate Looks Back - Jimmy Buffett Tribute Show
May
7
to May 9

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.

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Eddie Gossling
May
6
to May 9

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.

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Yin Yoga
May
5

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!

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Group Meditation Circle
May
4

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!

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One Night of Queen
May
3

One Night of Queen

One Night of Queen is a spectacular live concert that perfectly recreates the look, sound, pomp and showmanship of the greatest rock band of all time: Queen.
Gary Mullen & The Works bring the spirit and passion of rock icon Freddie Mercury to life on stage. As Brian May, original member of Queen, states, "(Gary Mullen has) more than a likeness." Hailed as the world's premiere Queen tribute band, they have received rave reviews from audiences worldwide. Fans of Queen will revel in this note-for-note experience of mega-hits like "Bohemian Rhapsody," "We Are the Champions," "Killer Queen" and many more. They will rock you and are guaranteed to blow your mind—the show does go on!

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