Join us for an enchanted evening of decorated historic inns while enjoying light sweet or savory holiday treats and holiday cheer at each property. Visit each property, explore the unique architecture and history, and delight in holiday ambiance in a tropical setting. The tours are self-guided. Free trolley transportation will be provided between properties - but participants are encouraged to bike, walk or use their own transportation.

Get ready for a holiday extravaganza like no other! Fiesta de Navidad is here to light up your season with beloved holiday characters and incredible Latin dance from salsa to cha-cha-cha. Highlighting the rich cultural influences that make Key West so unique, this show is a high-energy spectacle that will have everyone from kids to grandparents dancing.

Join us for an enchanted evening of decorated historic inns while enjoying light sweet or savory holiday treats and holiday cheer at each property. Visit each property, explore the unique architecture and history, and delight in holiday ambiance in a tropical setting. The tours are self-guided. Free trolley transportation will be provided between properties - but participants are encouraged to bike, walk or use their own transportation.

Join the Keys Choral Arts on Tuesday, December 17, 2024 at 7pm for their annual Winter Concert. “Christmas Re-imagined” will feature many of the carols that you have known for a life-time, traditional as well as newly-arranged settings, sure to please everyone.

 It's our first fundraiser of the season and a crowd favorite! Check-in at 7pm at the beautiful Gardens Hotel and enjoy a tasty beverage at the Garden's cash bar while you catch up with your Fringe friends and enjoy the live holiday music. Then at 8pm it's All Aboard our Holiday Train for a festive ride about town to see the holiday lights of Key West. Pickup and Return at the Gardens Hotel, 526 Angela Street. Tickets: $60.

Grammy-nominated record producer, John Simon, a titan behind the careers of The Band, Janis Joplin, and Leonard Cohen, comes to the Tennessee Williams Theatre for a unique and unforgettable evening – A Jazz Christmas.

Join the Key West Parrot Head Club on a Holiday Lights Trolley Tour!

See all the best decorations on our holiday tour as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition!

Ariel stunts, trampolines, funny skits, drinks, snacks, face-painting and more… SO MUCH FUN! Seating is limited to 125 guests so please do not wait to book.

“Tango in the Dark” follows two lovers as they journey through a city transformed by the shadows of nightfall weaving a story of love, loss, and connection fuelled by the rhythms of the city night.

Join the Keys Choral Arts on Tuesday, December 17, 2024 at Cellist Thomas Mesa and organist Greg Zelek will present a special duo concert showcasing the historic pipe organ at St. Paul’s Episcopal church. Mr. Mesa has established himself as one of the most charismatic, innovative, and engaging performers of his generation, and is the recipient of the Sphinx Organization’s 2023 Medal of Excellence, its highest honor. Mr. Zelek is the Principal Organist of the Madison Symphony Orchestra and Curator of the Overture Concert Organ, where he regularly performs and oversees all the MSO's organ programming. 

Immerse yourself in the deep, soothing and healing vibrations of the cello with world acclaimed cellist, composer, and multilingual vocalist Ian Maksin! In this concert, he will perform original instrumental music written throughout the years and recorded on several releases: Zaria, Sempre, Alchemist, Amor Renatus, as well as several songs from his collection in 37 languages.

Join us for a sophisticated afternoon at the Key West Woman's Club's Bougie Afternoon Tea for a Cause. Enjoy a delightful selection of gourmet teas, finger sandwiches, and delectable pastries while mingling with friends and supporting a worthy cause. Dress to impress and immerse yourself in the charm of Key West.

Join us as we raise funds to help support those in Asheville, NC after the devastating effects from Hurricane Helene. 

Tickets include food, live music, silent auction, and more. Cash bar.

South Florida Symphony Orchestra opens the 2025 Key West Season with Leonard Bernstein’s satirical Candide. This semi-staged concert version features the orchestra, a dynamic cast of actor-vocalists, minimal sets and costumes, and a chorus performing together on stage. 

Follow Candide on a riotous journey as he searches for "the best of all possible worlds," teeming with humor, unexpected twists, and profound philosophical reflections.

Cruising Through ‘The Change’, is a hilarious and heartfelt look at the joys of menopause and friendship — plus hot flashes, mood swings, memory lapses & more!

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.

Violinist Simone Porter has been recognized as an emerging artist of impassioned energy, interpretive integrity, and vibrant communication. In the past few years, she has debuted with the New York Philharmonic, the Philadelphia Orchestra, and the Los Angeles Philharmonic. Born in 1996, Simone made her professional solo debut at age 10 with the Seattle Symphony and her international debut with the Royal Philharmonic Orchestra in London at age 13.

Puppy Pals is a family fun action-packed show where adopted and rescued dogs perform spectacular stunts and breathtaking feats. Watch as we lead the puppies and audience through challenging and comical tricks as the pooches show everyone who is really boss!

Star from the hit TV show Will & Grace, Eric McCormack, and Tony nominated actress, Laura Bell Bundy, come to the Tennessee Williams Theatre! Together, they bring their magnetic chemistry from Broadway’s The Cottage to the stage, promising a night of unforgettable entertainment that spans Broadway hits, cinematic charm, and chart-topping tunes.

Named one of the greatest string quartets of the last 100 years by BBC Music Magazine, the two-time Grammy nominated Dover Quartet is one of the world’s most in-demand chamber ensembles. The quartet is the Ensemble in Residence at the Curtis Institute of Music and holds additional residencies at Northwestern University and the Walton Arts Center’s Artosphere festival.

Celebrate BIG GAME Sunday at The Marker Resort.

Enjoy a Tailgate Buffet and wine, draft beer, and premium well OPEN BAR.

Total ticket price is all inclusive of tax, gratuity, and fees.

An extravagant celebration of the iconic music of Broad­way and more, The Four Phantoms brings together four Phantoms from the Tony Award-winning The Phan­tom of the Opera for an unforgettable evening of entertain­ment.

Celebrate love in all its dramatic, poetic, erotic, scandalous and insatiable forms! Experience the thrilling return of R. Strauss’s swashbuckling escapade Don Juan alongside the South Florida Symphony Orchestra premiere of his touching Four Last Songs. Also featuring the world’s most famous waltz, J. Strauss II’s iconic Blue Danube, and Berlioz’s tumultuous King Lear Overture.

Get ready, Key West! The legendary Wearable Art Fashion Show is making a spectacular comeback on February 15th at the Hellings Curry Museum, home of the Key West Woman’s Club.

This electrifying evening will feature bold, one-of-a-kind designs in three categories: Tropical Couture, Creative Costume, and Eleanor’s Up-cycle—where donated garments are transformed into runway masterpieces. Bid live on these stunning creations and cheer on your favorites as designers compete for top honors!

Please join us for a Tropical Gala featuring a special tribute to our founder, Anne McKee.

Irie Monte returns to the Cabaret Theatre with her string quartet. Prepare to be enchanted as she graces the stage once again and immerse yourself in a captivating evening of music as Irie and her talented string quartet create a mesmerizing soundscape. Don't miss this extraordinary performance!

Avery Gagliano, pianist, is Impromptu’s 2025 “Rising Star”. Having made her debut at Carnegie Hall at the age of just 20, 22-year-old, Gagliano is an artist with ‘distinctive young talent’. Avery came to international acclaim as the First Prize and Best Concerto Prize winner at the 2020 National Chopin Piano Competition, and as the only American semifinalist at the 18th International Chopin Competition in 2021.

With a cast consisting of both stars from Broadway's greatest rock musicals, as well as incredible Rock & Roll singers, Neil Berg shares the often unknown stories from the fifty-year history of the music that changed the world forever!

Sam Carlson, the acclaimed singer-songwriter, takes the stage for a one-of-a-kind concert. In the first collaboration between Tennessee Williams Theatre and the Anne McKee Artists Fund, witness a performance that's sure to be unforgettable. Experience Carlson's soulful melodies and heartfelt lyrics in a setting that blends the magic of theater and the power of music.

Prague Conservatory of Music trained guitarist, Martina Bevis, returns to the Tennessee Williams Theatre. Join her along with her special guests, Marriane Nolan and Lynn-Marie Smith, to experience music from an artist who has mastered her instrument.

A pioneering oboe, bassoon, and piano ensemble, The Poulenc Trio has garnered international recognition over its 20-year history. With performances in 47 U.S. states and at prestigious music festivals around the world, including the Ravello Festival in Italy, the San Miguel de Allende Festival in Mexico, and the White Nights Festival in Russia, they have firmly established themselves as one of the most active and sought-after touring piano-wind ensembles in the country.

outh Florida Symphony Orchestra, led by Key West native Maestra Sebrina Alfonso, closes the 2025 Season with an all-Mozart evening. His enigmatic Requiem is one of the most iconic compositions ever. Characterized by its sorrowful yet transcendent melodies, powerful choral passages – performed by dazzling singers and the South Florida Symphony Chorus -- and orchestral depth, the haunting beauty and emotional intensity of his Requiem Mass has captivated listeners for centuries.

Seamlessly blending illusion, acrobatics, magic, and whimsy, MOMIX sends audiences flying down the rabbit hole in Moses Pendleton’s newest creation, ALICE, inspired by Lewis Carroll’s classic Alice in Wonderland.

International competition winning ensemble Duo Beaux Arts was formed in 2008 by world renowned husband and wife concert pianists and recording artists Catherine Lan and Tao Lin. Known for their adrenalized performances, this dynamic Duo has performed across Europe, the US, and China, to critical and audience acclaim.

THE PEKING ACROBATS® have redefined audience perceptions of Chinese acrobatics. They perform daring maneuvers atop a precarious pagoda of chairs and display their technical prowess at such arts as trick-cycling, precision tumbling, juggling, somersaulting, and gymnastics.

Get ready for an epic live show with Free Fallin, The Tom Petty Concert Experience!

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.

Buckets N Boards is a hilarious and high-energy show chock-full of amazing percussion, ridiculous songs, spectacular tap dancing, inventive instrumentation and an incredible variety of musical talents!

RING–A-DING-DING! THE BEST RAT PACK SHOW RE-TURNS! Frank Sinatra, Dean Martin and Sammy Davis, Jr. return to stages all across America as the famous and infamous Rat Pack is resurrected by our three critically acclaimed entertainers. Sinatra, Martin and Davis were the kings of Las Vegas Swing and they formed The Rat Pack as their own nightly on-stage party. Relive those amazing nights with our international star performers.