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.

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!

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.

Enjoy this vibrant musical journey remembering the one and only, Tom Petty!  Watch as these highly skilled musicians perform his iconic hits. Perfect for those who’ve grown up to classics like ‘American Girl’, ‘Free Fallin’ and ‘Mary Jane’s Last Dance’. 

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.

Travel down the rabbit hole MOMIX-style with Moses Pendleton's newest creation, ALICE, inspired by Alice in Wonderland. As Alice’s body grows and shrinks and grows again, Pendleton’s dancers extend themselves by means of props, ropes, and other dancers.

South 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. Mozart’s Symphony No. 40, daring, evocative and dripping with emotion, cements Mozart’s status as one of music’s greatest innovators.

Joy Hawkins debuts in the Tennessee Williams Cabaret Theatre with stories and songs from her life. Joy is a multifaceted talent who has made significant contributions to both stage and screen. Her career spans over four decades, showcasing her versatility as an actress, director, and entertainer.

Joy Hawkins debuts in the Tennessee Williams Cabaret Theatre with stories and songs from her life. Joy is a multifaceted talent who has made significant contributions to both stage and screen. Her career spans over four decades, showcasing her versatility as an actress, director, and entertainer.

The CoffeeMill Young Dance Collective's (CYDC) annual benefit concert at the Tennessee Williams Theatre! 

A classical guitar from Prague, Martina Bevis has graced the stage of the Tennessee Williams Theatre in previous collaborations.

A collaboration with Tennessee Williams Theatre and the Anne McKee Artist Fund Fund will present singer/songwriter Sam Carlson.

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!

Bobby Nesbitt returns to the TWT Cabaret in his acclaimed series Bobby in the Lobby with a celebration of Irving Berlin, the godfather of the Great American Songbook.

Bobby Nesbitt returns to the TWT Cabaret in his acclaimed series Bobby in the Lobby with a celebration of Irving Berlin, the godfather of the Great American Songbook.

Irie Monte returns to the Cabaret Theatre with her string quartet.

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.

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

Eric McCormack and Laura Bell Bundy! 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.

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!

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.

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!

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.

“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.

John Simon, veteran record producer of such acts as The Band, Blood, Sweat & Tears, Janis Joplin, Leonard Cohen and others, presents a joyous celebration of the marriage of a rich holiday repertoire with America’s true Art Form: jazz.

A sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City – Key West's very own NUTCRACKER!

A sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City – Key West's very own NUTCRACKER!

A sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City – Key West's very own NUTCRACKER!

A sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City – Key West's very own NUTCRACKER!

A sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City – Key West's very own NUTCRACKER!