Dave Williamson
Mar
4
to Mar 7

Dave Williamson

Named “Best Comedian in Miami” by the Miami New Times, Dave Williamson tours heavily, both headlining his own shows and as the supporting act for Bert Kreischer. His second album, “Trying My Hardest” was just released by Stand Up! Records and reached #1 in the iTunes Charts for Comedy. Dave's material is in heavy rotation on many SiriusXM stations. Dave often talks about family, highlighting stories from his youth to navigating the role of Father & husband himself. He is obsessed with BBQ, and hosts his own podcast called “Meat Dave”.

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Burgers & Buffett Tunes: A Tribute Show
Mar
5
to Mar 7

Burgers & Buffett Tunes: A 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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Hemingway in a Funny Way
Mar
6

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.

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Book Sale in the Palm Garden
Mar
7

Book Sale in the Palm Garden

Held monthly in the Library Palm Garden from December to March, the Friends of the Key West Library Book Sale is a place that brings the community together. It is amazing what gems can be found among the 3,000 donated books: a book or two, a friend or two, a good conversation, or even a book for a gift. There is always a line of customers waiting for the gates to open.

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Diamonds are a Girls Best Friend
Mar
7

Diamonds are a Girls Best Friend

  • Hellings Curry Museum, home of the Key West Woman's Club (map)
  • Google Calendar ICS

On Saturday, March 7, the Key West Woman’s Club will host its annual fundraiser Diamonds are a Girls Best Friend!

 Enjoy an open bar, fully catered dinner, lively music by Skipper Kripitz & friends, and dancing while you shine in your diamonds!  

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Conch Fest: Red Eye Gravy Brunch
Mar
8

Conch Fest: Red Eye Gravy Brunch

Step into Old Key West with a special brunch by Chef Martha Hubbard celebrating iconic conch comfort food and classic Southern flavors with a thoughtfully prepared three-course menu.

*Please Note: Due to unforeseen circumstances, Wilhelmina Lopez-Martin will no longer be able to perform at the brunch.

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Bobby in the Lobby
Mar
8
to Mar 9

Bobby in the Lobby

No songwriter ever composed more hits for the Broadway musical than Richard Rodgers. Starting in the mid 1920s  his collaboration with the brilliant Lorenz Hart and continuing with his record-breaking partnership with Oscar Hammerstein, Richard Rodgers was the defining voice of 20th Century Broadway. Join Bobby Nesbitt along with Susan Powell and Richard White as they celebrate this timeless music. Act One comprises the songs of Rodgers and Hart including “Manhattan”, “Bewitched”, “Where or When”, “My Funny Valentine” and many more.

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Acupuncture
Mar
9

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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Yang Yoga
Mar
10

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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Crimes of the Heart
Mar
11
to Mar 21

Crimes of the Heart

Beth Henley’s beloved Pulitzer Prize winning script. Three eccentric sisters. A forgotten birthday, a failed career, an attempted murder. Funny. Messy. Filled with southern comfort. Featuring Martha Hooten-Hattingh, Sarah-Hunter Wald, Abigail Emerson, Samantha Laskey, Dan Dempsey, and Dominic Paolillo.

Tickets: $45-$65 (does not include fees)

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Ladies Night with Larry Smith
Mar
11

Ladies Night with Larry Smith

Ladies Night with Larry Smith is a weekly musical showcase hosted at the Key West Cultural Center & Veterans Museum. This event is open to the public and features a rotating lineup of talented female vocalists throughout the month of March.

March 11 Line-up:
Anna Coppa: A Texas-born singer recognized for her smooth and silky delivery.
Genevieve Esapa: A singer and songwriter from Ellenwood, Georgia, who specializes in country blues, jazz, and soul.

FREE!

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The Doo Wop Project
Mar
11

The Doo Wop Project

Featuring stars from the Broadway shows Jersey Boys, Motown, Beautiful and Hairspray,  Doo Wop Project is inspired by inner city African American vocal groups like The Flamingos, The Five Satins, The Miracles and later The Four Seasons, along with all the original groups that created the sound of Doo Wop. 

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Cory Michaelis
Mar
11
to Mar 14

Cory Michaelis

Cory has a Dry Bar Comedy Special -"Bad Teacher" - that snagged over 80 million views. His debut album, "The Collage Dropout," was released by 800 Lb. Gorilla Records and charted at #2 on iTunes & Billboard (because it was the only album released that week). Cory was a finalist in the Seattle Comedy Competition which means he didn't win and was in Season 2 of Netflix's "Huge in France" with Gad Almelah.

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Burgers & Buffett Tunes: A Tribute Show
Mar
12
to Mar 14

Burgers & Buffett Tunes: A 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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Hemingway in a Funny Way
Mar
13

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.

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FKSPCA 18th Annual Spring Social 2026
Mar
13

FKSPCA 18th Annual Spring Social 2026

Tickets are on sale NOW for our 18th Annual Spring Social presented by Hank's Hair of the Dog Saloon! Join us for our biggest celebration of the year at the Truman Little White House on Friday March 13th. VIP tickets include a Champagne Reception starting at 5:30pm before the main event, passed appetizers, a sneak peek at the silent auctions, and reserved seating.

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Tennessee Rising: The Dawn of Tennessee Williams
Mar
13
to Mar 14

Tennessee Rising: The Dawn of Tennessee Williams

Brought to you in partnership with the Key West Art & Historical Society and presented as part of the Tennessee Williams Key West Festival.

Prepare for an intimate theatrical experience with Jacob Storms’ internationally acclaimed solo play, TENNESSEE RISING: The Dawn of Tennessee Williams (originally directed for the stage by Alan Cumming).

This powerful biographical work sheds much-needed light on the unexplored, formative years of Thomas Lanier Williams on his journey to becoming the iconic playwright Tennessee Williams. Written and performed by United Solo Award winner Jacob Storms, TENNESSEE RISING offers a poignant look at the influences and events that shaped America’s greatest dramatist — and created his most iconic character: himself.

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Jammy Buffet Live!
Mar
13
to Mar 14

Jammy Buffet Live!

Join us for Jammy Buffet Live, featuring Jimmy Buffett's lead guitarist and accomplished songwriter, Peter Mayer. 

Jimmy Buffett often spoke of “traveling the songlines,” a phrase borrowed from the Aboriginal tradition of mapping the land through music and story—paths that connect people, places, and moments across time. Jammy Buffet picks up that journey, where Buffett’s coastal storytelling meets the improvisational spirit of the jam band world.

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South Florida Symphony Orchestra: Dvořák’s Eighth & Sibelius’ Violin Concerto
Mar
14

South Florida Symphony Orchestra: Dvořák’s Eighth & Sibelius’ Violin Concerto

Sibelius’s soul-searching Violin Concerto, featuring the expressive brilliance of guest artist Siwoo Kim, and Dvořák’s Bohemian-folk inspired Symphony No. 8 highlights music’s ability to connect to worlds unknown. One looks inward, tracing shadows and emotion; the other bursts outward in celebration of nature, life, and song. Opening the South Florida Symphony Orchestra program – led by Key West native Maestra Sebrina Alfonso -- is Schubert’s Overture in D major, a playful wink to Rossini’s Viennese operas.

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Carr-Petrova Duo
Mar
15

Carr-Petrova Duo

Described as "ravishing" (Strad), "enlightened" (BBC), "explosive" (Virginia Gazette), and "irresistibly elegant" (Diario de Leon), violist Molly Carr and pianist Anna Petrova are rapidly compiling a remarkable list of accolades in recognition of their fiery musical expression, refined artistry, and relentless entrepreneurial dedication to social initiatives.

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Bad Teachers w/ Cory Michaelis and friends
Mar
15

Bad Teachers w/ Cory Michaelis and friends

Teachers (and former students) of Key West! Celebrate your long weekend with the comedy of a teacher who couldn't cut it - Cory Michaelis. After 12 years of teaching high school, Mr. Michaelis decided drunken hecklers were easier to deal with than students. Come see two class periods worth of mostly teacher/student material relatable to anyone who has ever been in a classroom. Non-teachers and teachers alike will love this show and some admin. will be on the show to keep us all in line. Irreverent (but PG-13-ish) comedy, shot specials, prizes, and a Kahoot!

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Group Meditation Circle
Mar
16

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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Yin Yoga
Mar
17

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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Ladies Night with Larry Smith
Mar
18

Ladies Night with Larry Smith

Ladies Night with Larry Smith is a weekly musical showcase hosted at the Key West Cultural Center & Veterans Museum. This event is open to the public and features a rotating lineup of talented female vocalists throughout the month of March.

March 18 Line-up:
Adrienne Z: A unique singer/songwriter who is well-known and respected across the Keys.
Leanne Collins Hettinger: A former island singer/songwriter and current Michigan resident making a welcomed return to Key West.

FREE!

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Sean Finnerty
Mar
18
to Mar 21

Sean Finnerty

From Longford, Ireland, Sean Finnerty decided to move stateside where a series of mature decisions that he failed to make led him to stand-up comedy. Recently he was rewarded for his efforts as he became the first ever Irish comedian to perform on the Tonight Show with Jimmy Fallon. Spending his first number of years in comedy based out of Orlando, Sean was selected for Comedy Central’s Up Next competition, made his television debut as co-host of Season 9 of Fireball Run on Amazon Prime. He has also performed at several festivals including Laugh Your Asheville Off, Edinburgh Fringe, and Electric Picnic, along with making it to the semi finals of the nationwide talent search Stand Up NBC. A keen eye for detail Sean has also developed a reputation as a Roaster and is currently the number 1 ranked roast comic in New York City.

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Burgers & Buffett Tunes: A Tribute Show
Mar
19
to Mar 21

Burgers & Buffett Tunes: A 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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The Italian American Dream with Analisa and John
Mar
19

The Italian American Dream with Analisa and John

Experience a truly authentic and unforgettable performance by Nashville’s own Analisa and John Gallo. This evening supports the local charities of the Sons and Daughters of Italy Key West Lodge.

  • Schedule: Dinner at 5:30 PM | Show starts at 6:45 PM

  • Admission: $50 (Includes dinner & one glass of wine)

"The Italian American Dream" show honors the story of the Italian immigrants of the early 1900s. It is a show for everyone, and highlights the themes of culture, family, sacrifice, and faith!

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Mocktails & Manuscripts
Mar
19

Mocktails & Manuscripts

The doors of the Hemingway Home will swing open for an unforgettable event Thursday, March 19th, 2026. Top mocktail creators will gather to mix, mingle, and compete for the coveted title of “Master Mixologist 2026”. The food pairing highlights the key skills of pairing food to enhance the mocktail experience. 

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Hemingway in a Funny Way
Mar
20

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.

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Vintners Dinner
Mar
21

Vintners Dinner

The iconic Vintners Dinner returns in 2026! “The ART of Tasting” is a chef-curated food and wine experience—an elegant evening of fine wines, delicious cuisine, and heartfelt community connection in beautiful, historic Williams Hall. Guests will enjoy a thoughtfully crafted multi-course tasting menu by Chefs John Corea and David Fuhrman, perfectly paired with exceptional wines presented by Pacific Southern Wine Company and Republic National Distributing Company. Erin McKenna hosts the evening of live music, Fine Wine & Cuisine, as we raise a glass to AH Monroe's four decades of compassion, innovation, and impact in the Keys. 

Join us for an artful evening of wine, cuisine, and community connection!

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Paradise Big Band
Mar
22

Paradise Big Band

Under the baton of Joe Dallas Jr, the band remains a truly "local" organization consisting of professional and semi-professional musicians from the Lower Keys and primarily Key West. In the interest of enhancing both solo and ensemble performances, the band regularly features outstanding guest artists from New England, New York City and Pittsburgh.

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Acupuncture
Mar
23

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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Cheers to 10 Years!
Mar
23

Cheers to 10 Years!

It’s a Celebration! The Fringe Board invites you to join us on March 23rd as we celebrate ten years with Rebecca Tomlinson as Fringe’s Managing Artistic Director. We’re celebrating the people, the shows, and the direction that has led Fringe Theater through its unprecedented growth. Join us for music, food, and memories!

Your ticket price includes the Ericson Holt Band, Food stations and hors d'oeuvres, Open Bar. We’ve memories to share and new memories to make!

Sponsored by William & Pattye Monroe, Blake Hunter & Murphy Davis, Dennis Beaver & Bert Whitt, Neal Ruchman & Melissa Jean McDaniel, The Gardens Hotel, Billy Cartledge & Jim Hall, and Janet & Charlie Bengel.

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Taste of Key West
Mar
23

Taste of Key West

Join us for one of Key West’s most anticipated foodie traditions! 🌴🍷
Taste of Key West returns for its 31st Annual Celebration, bringing together the island’s top restaurants, vintners, and beverage partners for an unforgettable open-air evening at Truman Waterfront.

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Yang Yoga
Mar
24

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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Swing Dance Night with the Paradise Swing Band
Mar
24

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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Ladies Night with Larry Smith
Mar
25

Ladies Night with Larry Smith

Ladies Night with Larry Smith is a weekly musical showcase hosted at the Key West Cultural Center & Veterans Museum. This event is open to the public and features a rotating lineup of talented female vocalists throughout the month of March.

March 25 Line-up:
Camille Russo Toler: A beloved local favorite proficient in performing soul, jazz, and rock music.
Jamie Olwell: A 44-year resident of Key West who sings with passion in her own unique, sweet style.

FREE!

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Jimmy Dunn
Mar
25
to Mar 28

Jimmy Dunn

Jimmy Dunn is a stand-up comedian and actor from Boston, who currently plays “Moose” on the Paramount+ reboot of the iconic sitcom FRASIER. ​He can be heard most Tuesdays on The Greg And The Morning Buzz radio network. He got his start in "show business" telling jokes in a bar in Gloucester, Massachusetts, where he was paid in beer and fried clams. Since then, he’s gone on to perform at some of the world’s most prestigious comedy events, including the Late Show with David Letterman, CONAN, Montreal’s International Just For Laughs Comedy Festival, and Denis Leary’s Comic’s Come Home in Boston. Jimmy’s first major television role was as Sean McCarthy on the ​CBS sitcom, THE MCCARTHYS. He’s also written on several television projects, including two episodes of LOUDERMILK that he co-wrote with Academy Award winner Peter Farrelly.​

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Dealing with Tough Customers and Colleagues: Practical Skills for the Workplace and Beyond
Mar
26

Dealing with Tough Customers and Colleagues: Practical Skills for the Workplace and Beyond

Learn tools you can apply to your life immediately to:

  • Calm people down when they are angry

  • Resolve conflict quickly and effectively

  • Turn unhappy customers around

  • Deal with negativity without it getting you down

  • Say no effectively…and much more!

 Elisa Levy is a speaker and author, who has travelled the world teaching conflict resolution, leadership and customer service. Her clients run the gamut from major hotel chains, fortune 500 companies, the United Nations and nonprofit organizations.

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Burgers & Buffett Tunes: A Tribute Show
Mar
26
to Mar 28

Burgers & Buffett Tunes: A 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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The College of the Florida Keys 60th Anniversary Celebration
Mar
27

The College of the Florida Keys 60th Anniversary Celebration

Toast to six decades of educational excellence at The College of the Florida Keys’ milestone 60th Anniversary Celebration, featuring fine dining, cocktails, historical exhibit, live music by Bay Kings Band, and dancing in honor of the College's rich legacy and continued commitment to student success.

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Stories & Supper With Lucy Burdette
Mar
27

Stories & Supper With Lucy Burdette

Join us for a special literary evening featuring Lucy Burdette, USA Today bestselling author of the beloved Key West Food Critic mystery series. Enjoy a live reading of one of Lucy’s short stories by local creative and actress Erin McKenna, followed by dinner prepared by Chef Martha and conversation celebrating storytelling and community.

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Keys Choral Arts: "Songs for the People"
Mar
27

Keys Choral Arts: "Songs for the People"

Presented at the Key West United Methodist Church, the spring concert, "Songs for the People" will in part, honor the many women composers and artists of our time, featuring new compositions and arrangements by women. This will also feature a set of American Spirituals, with guest artist, dramatic soprano Dr. Amy Yekel.

A reception will follow the concert.

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And Tell Sad Stories of the Death of Queens
Mar
29

And Tell Sad Stories of the Death of Queens

Little-known short plays by Tennessee Williams that boldly explore sexuality, identity, and longing. Presented in partnership with the Tennessee Williams Festival at Williams Hall. Directed by Dominic Paolillo. Cast: Kitty Clements, Cassidy Timms, Aramis Ikatu, Phillip Cole, Todd Glenn, Jim Speake, Trey Forsyth, Diane May, Chris Massicotte, Kathy Russ, Mariah Woessner, Davis Stack, Barbara Mundy.

 

Venue: Williams Hall, 729 Fleming St.

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Houston Ballet II
Mar
30

Houston Ballet II

Houston Ballet II (HBII) is the second company of Houston Ballet, America’s fifth largest ballet company. Comprised of a stellar array of ballet students from around the world, HBII members perform a diverse range of dance works such as excerpts from the great classics including The Sleeping BeautySwan Lake, and The Nutcracker to contemporary works by Houston Ballet Artistic Director, Stanton Welch AM.

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Jessimae Peluso
Apr
1
to Apr 4

Jessimae Peluso

Jessimae Peluso is a stand-up comedian, writer, performer, TV and podcast host whose work blends raw comedy with emotional depth. Known for her breakout role on MTV’s Girl Code and hosting Netflix’s Tattoo Redo and Surviving Paradise, Jessimae has spent nearly two decades turning personal pain into punchlines.

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Burgers & Buffett Tunes: A Tribute Show
Apr
2
to Apr 4

Burgers & Buffett Tunes: A 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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Habitat for Humanity's Tropical Gala
Apr
2

Habitat for Humanity's Tropical Gala

Habitat for Humanity of Key West and Lower Florida Keys provides affordable homeownership opportunities to low-income working families and critical home repairs to our community’s vulnerable elderly population. We are dedicated to empowerment, not entitlement, and bringing people together to build homes, communities, and hope. As a locally supported nonprofit the work we do is only made possible through support from the community. Proceeds from Habitat’s 2025 sold-out gala helped provide 9 families with affordable, safe homes to call their own, 5 senior household with critical home repairs allowing them to age in place, and 27 families with affordable rentals.

Our 2026 event will feature a delicious dinner, creative libations, and inspiring program, games, auctions, dancing and an all-around memorable evening. We invite you to attend, sponsor, and be recognized as we come together again in 2026 for a fun evening to change lives and build a better community.

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Group Meditation Circle
Apr
6

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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Steve Rannazzisi
Apr
8
to Apr 11

Steve Rannazzisi

For over 13 years, from the stage to the silver screen, Steve Rannazzisi has made audiences laugh. Currently, Rannazzisi stars and writes alongside Katie Aselton, Mark Duplass, Nick Kroll, Jonathan Lajoie, and Paul Scheer on the critically acclaimed FX Network comedy series, The League, which is produced by Jeff and Jackie Schaffer.

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Burgers & Buffett Tunes: A Tribute Show
Apr
9
to Apr 10

Burgers & Buffett Tunes: A 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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"Endless Summer" Fundraiser with Howard Livingston & friends
Apr
11

"Endless Summer" Fundraiser with Howard Livingston & friends

Get ready to escape to the islands for a great cause at the "Endless Summer" Fundraiser with Howard Livingston & friends! This special event is more than just a concert; it's an unforgettable evening of high-energy "Trop Rock" music featuring Key West's own Howard Livingston & The Mile Marker 24 Band.

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Acupuncture
Apr
13

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 →
Gastor Almonte
Apr
13
to Apr 14

Gastor Almonte

Gastor Almonte is a Dominican-American stand-up comedian, writer, and podcaster based in New York City. Raised in Brooklyn, he’s known for his warm, thoughtful delivery and deeply personal storytelling—blending culture and identity into comedy that’s both smart and emotionally grounded. Gastor has been featured on Comedy Central and NBC, and he performs regularly at top clubs and theaters across the country. His work has also appeared at major comedy festivals and across digital platforms, where he’s earned a reputation as a comedian’s comedian—respected for his writing, honesty, and point of view.

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The Shark is Broken
Apr
15
to Apr 25

The Shark is Broken

Written by Ian Shaw and Joseph Nixon

​The Hit of the Edinburgh Fringe 2019

 

Three actors. One small boat. Alcohol flows. Egos clash. A cinematic shoot that will make history -- assuming someone can figure out how to fix that blasted shark. This 'bitingly funny' play is the true story of behind the scenes of the movie JAWS. ​Starring: Trey Forsyth, Mathias Maloff, and Ray West.

 

Tickets: $45-$65 (does not include fees)

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Amos Gill
Apr
15
to Apr 18

Amos Gill

Amos Gill is one of Australia’s hottest comedians, now making waves internationally as a touring headliner across the USA, UK, and Australia. Known for his sharp humor and quick wit, Amos first gained attention as a beloved Adelaide radio host on Amos, Cat & Angus. After leaving radio in 2018, he quickly became a comic to watch, earning accolades such as runner-up in triple j’s RAW Comedy competition and hosting the Melbourne International Comedy Festival’s prestigious Comedy Zone.

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Burgers & Buffett Tunes: A Tribute Show
Apr
16
to Apr 18

Burgers & Buffett Tunes: A 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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4th Annual FRLA Monroe R.O.S.E Awards
Apr
16

4th Annual FRLA Monroe R.O.S.E Awards

The ROSE (Recognition of Service Excellence) Awards recognizes Monroe County front line hospitality employees who demonstrate excellent customer service. These industry champions showcase the region’s commitment to creating an extraordinary visitor experience.

Sponsorship opportunities available.

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Movies Under the Stars: Shrek
Apr
18

Movies Under the Stars: Shrek

Join us for a magical, family-friendly evening under the stars with a screening of the beloved 2001 animated hit Shrek!

Follow a grumpy but lovable ogre on a hilarious quest to rescue a feisty princess with the help of a talking donkey and a whole lot of fairy tale twists.

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Group Meditation Circle
Apr
20

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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Tony V
Apr
22
to Apr 25

Tony V

In 1986 Tony V was named “Funniest Person in Massachusetts” by Showtime television. He followed this achievement with several performances on HBO, the Arts and Entertainment Network, Comedy Central and MTV. From 1987 through 1992 Tony V became the “spokesperson” for American Tourister Luggage. Remember the suit case smashing gorilla? It was Tony that gave the ape it’s distinct voice and temperament. Touring extensively in and out of his high tech forty-five thousand dollar yak hair gorilla suit, both Tony and his alter ego had many interesting adventures. If you get a chance ask Tony about a meeting between The Gorilla, Spuds MacKenzie and Ronald McDonald. You won’t believe your mind.

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Burgers & Buffett Tunes: A Tribute Show
Apr
23
to Apr 25

Burgers & Buffett Tunes: A 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
Apr
27

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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Swing Dance Night with the Paradise Swing Band
Apr
28

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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Long Live Lambada!
Apr
28
to Apr 30

Long Live Lambada!

Dust off your dancing shoes and get ready for a theatrical heatwave because the “Forbidden Dance” is making a scorching comeback! From April 28 to April 30, 2026, the Tennessee Williams Theatre transforms into a pulse-pounding portal to Brazil as the Key West International Dance Company presents the high-octane spectacle, Long Live Lambada! This isn’t your typical night at the ballet; it’s a "crazy, sexy," and wildly immersive celebration with world-class choreography.

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Burgers & Buffett Tunes: A Tribute Show
Apr
30
to May 2

Burgers & Buffett Tunes: A 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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Burgers & Buffett Tunes: A Tribute Show
May
7
to May 9

Burgers & Buffett Tunes: A 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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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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Burgers & Buffett Tunes: A Tribute Show
May
14
to May 16

Burgers & Buffett Tunes: A 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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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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Burgers & Buffett Tunes: A Tribute Show
May
21
to May 23

Burgers & Buffett Tunes: A 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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Burgers & Buffett Tunes: A Tribute Show
May
28
to May 30

Burgers & Buffett Tunes: A 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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Swing Dance Night with the Paradise Swing Band
Jun
2

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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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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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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Ladies Night with Larry Smith
Mar
4

Ladies Night with Larry Smith

Ladies Night with Larry Smith is a weekly musical showcase hosted at the Key West Cultural Center & Veterans Museum. This event is open to the public and features a rotating lineup of talented female vocalists throughout the month of March.

March 4 Line-up:
Katy Werner: A singer/songwriter from Pennsylvania who charms her audience with a delivery described as both sweet and sultry.
Renee Breslin: Hailing from New Jersey, Renee has been performing as a singer in Key West since 2020.

FREE!

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Illusionist Rick Thomas
Mar
3

Illusionist Rick Thomas

Step into the Extraordinary as Rick Thomas takes you on a journey never to be forgotten…a journey within his Mansion of Dreams! Prepare to be captivated by the mesmerizing world of one of the greatest illusionists on the planet. People of all ages will experience amazing and magical things as they witness the beauty and mysteries behind the Mansion’s magnificent walls. Contained within the production are the most intriguing, innovative and mind-blowing grand illusions in the world.

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Yin Yoga
Mar
3

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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Speaker Series: Bob Rich
Mar
2

Speaker Series: Bob Rich

Noted American businessman Bob Rich is an avid outdoorsman and the author of five books, including Fish Fights, The Fishing Club, and The Right Angle. His novel, Looking Through Water, was awarded a gold medal by Readers’ Favorite in the category of Southern Fiction and has been made into a film now streaming on multiple platforms, including Amazon, Apple TV, Fandango at Home, and Google Play.

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George Li
Mar
1

George Li

Pianist George Li, is Impromptu’s 2026 “Rising Star”. Praised by the Washington Post for combining “staggering technical prowess, a sense of command and depth of expression,” he possesses an effortless grace, poised authority, and brilliant virtuosity far beyond his years.

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Hemingway in a Funny Way
Feb
27

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.

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Burgers & Buffett Tunes: A Tribute Show
Feb
26
to Feb 28

Burgers & Buffett Tunes: A 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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James Yon
Feb
25
to Feb 28

James Yon

This Florida native is one of America's hottest up and coming comedians. He can be seen each and every Sunday at 11pm hosting his own show, "Viral Breakdown" on the Afrotainment Channel on Dish Network. He has graced the stage with some of America’s top talent including, Joe Torry, Jimmy J.J Walker, Tom Rhodes and Michael Winslow. He was a finalist for NBC’s stand up for Diversity and appeared on the FOX comedy club. He was the 2011 and 2012 winner of the Orlando Improv’s “Clash of the Comics.” Now James spends his time touring clubs and casinos all over the country from Orlando to Las Vegas bringing the funny.

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Tom Dustin
Feb
24

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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Yang Yoga
Feb
24

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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USMC Birthday Dinner Fundraiser
Feb
23

USMC Birthday Dinner Fundraiser

Join the community for a special evening celebrating the United States Marine Corps while supporting a worthy cause. This fundraiser, hosted in partnership with Neeley Family Distillery, promises an evening of camaraderie, fine spirits, and celebration.

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A FEAST OF WORDS AND FLAVORS WITH RUTH REICHL
Feb
23

A FEAST OF WORDS AND FLAVORS WITH RUTH REICHL

Celebrate the magic of books, food, and community at the Friends of the Key West Library Gala—an unforgettable evening with a culinary legend.

Join us Monday, February 23, 2026, for the Friends of the Key West Library Fundraising Gala, featuring legendary food writer Ruth Reichl—author, critic, and culinary icon. Enjoy her exclusive interview, then mingle in the Palm Garden with delicious bites, tropical cocktails, and twinkling lights. Proceeds benefit the Key West Library—so come celebrate great books, great food, and our beloved little pink library!

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Acupuncture
Feb
23

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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Master Debaters
Feb
22

Master Debaters

Master Debaters is a live comedy debate show where stand-up comics argue ridiculous, relatable, and sometimes controversial topics—armed only with jokes, hot takes, and zero preparation. It’s fast, unpredictable, and fueled by crowd energy, with no topic off-limits and no debate ever taken seriously. Comics go head-to-head debating absurd topics in this high-energy live comedy show. Part stand-up, part roast, part chaos—Master Debaters delivers big laughs, bold opinions, and audience-driven moments every round.

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South Florida Symphony Orchestra: Rimsky-Korsakov’s Capriccio espagnol, with Mozart, Simon & Joachim
Feb
21

South Florida Symphony Orchestra: Rimsky-Korsakov’s Capriccio espagnol, with Mozart, Simon & Joachim

The familiar meets the new in this South Florida Symphony Orchestra standout program, featuring the anticipated Florida premiere of GRAMMY nominee Nathalie Joachim’s Had to Be, an intimate exploration of memory and identity, performed by rising cellist Seth Parker Woods. Also making its SFSO premiere is Carlos Simon’s Four Black American Dances, a vibrant work filled with cultural reverence. Completing the program led by Key West native, Maestra Sebrina Alfonso, Mozart’s “Haffner” symphony bursts with celebratory energy and elegant precision, while the crowd-pleasing Capriccio espagnol by Rimsky-Korsakov sparkles with irresistible Spanish rhythms.

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Caitlin Peluffo
Feb
20
to Feb 21

Caitlin Peluffo

Caitlin Peluffo has been featured on the Late Show with Stephen Colbert, The Late Late Show with James Corden, After Midnight, 2022’s Just For Laughs Festival, and has hosted her weekly podcast, Good Time Gal with Caitlin Peluffo for over three years. She has also been featured on Comedy Central’s “Featuring” series, and has a Don’t Tell Comedy Set with over 150k views on YouTube. With Caitlin, no subject is off limits, however, she did make a promise to her mother that she would never, ever discuss that one time she took those ‘whorish, yet tastefully executed’ photos for a guy she used to bang in the military. She may be a patriot, but a promise is a promise.

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Letters from Max
Feb
20

Letters from Max

This poignant and deeply intimate play premiered off-broadway in 2023 at Signature Theater in NYC. Witty and deeply human. It explores the emerging friendship of a professor and her student Max. Their love of words bind them in a  wide and voracious conversation that eventually tests poetry's capacity to put to words the ineffable.  Based on a true story. An Outer Critics Circle Nominee. Featuring Wende Shoer and Thomas Masat.  

Tickets: $45-$65 (does not include fees)

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Hemingway in a Funny Way
Feb
20

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.

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The Best Diet and Other Myths About Nutrition
Feb
19

The Best Diet and Other Myths About Nutrition

Licensed dietician, nutritionist, and health educator, Leigh Pujado will discuss how the internet and social media bombard us with confusing and conflicting nutrition and dietary advice, many of us are left wondering what’s fact and what’s fiction! Gain science-based insights that will empower you to make choices right for you. You’ll learn about the evolution of nutrition advice, where dietary guidance took some wrong turns, and how that launched decades of fad diets. Leigh will include a little biochemistry so that you can understand how the body responds to certain foods to better equip you to choose foods that sustain health.

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Burgers & Buffett Tunes: A Tribute Show
Feb
19
to Feb 20

Burgers & Buffett Tunes: A 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
Feb
17

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 →
Brothers From Another Mother Comedy Tour
Feb
15
to Feb 17

Brothers From Another Mother Comedy Tour

Jackie Flynn is a seasoned Boston-bred comedian and actor who has transitioned from legendary stand-up stages like The Comedy Store to a prolific screen career. Beyond his "Man Law" commercial fame, Jackie has appeared in The King of Queens and Veep. He currently stars as "Tony" in the Peter Farrelly-directed series Loudermilk.

Kevin Flynn has thrilled audiences for years with his stand-up comedy performances having headlined at clubs and colleges across the country. Flynn’s career as a comedian took off after winning the Boston Comedy Riot in 1988, where he then began appearing on numerous comedy specials. He has since added several film and television credits to his name appearing in The Heartbreak Kid with Ben Stiller; Me, Myself and Irene with Jim Carrey; Osmosis Jones with Billy Murray, and Sex and the City.

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