
SWAYZEES PAJAMA POOL PARTY AT SOMO’S SHORES POOL
Grab your PJs or your swimsuit (or both) and come dance, swim and drink with Les Greene and the Swayzees!

PAST YOUR BEDTIME: A Surreal Extravaganza
Transforming 801 Bourbon Bar + Upstairs Cabaret + Saloon 1
LIVE MUSIC ORIGINAL ART LOCAL TALENT CIRQUE BURLESQUE DRAG COMMEDIA DELL'ARTE * LIVE ENTERTAINMENT ALL NIGHT LONG
The Hush Hush Theatre is a pop-up theatre exploring new realms of storytelling through live music, dance, burlesque, drag, comedy and cirque. We encourage new talent, original work and the unconventional.

Shoreline Sessions
Get ready for Shoreline Sessions presented by Island 106.9 KW Radio and Southernmost Beach Resort & Guesthouses in Key West! This epic two-day music event features Fortunate Youth and a fantastic lineup of artists.

Fall Showcase
Join us for the Drama Club’s 2025 Fall Showcase Fundraiser!
This year’s theme, Coming of Age, explores the moments that shape us — stories of growth, change, and finding our place in the world — all told through the voices and talents of high school students from our Key West community.

Fall Showcase
Join us for the Drama Club’s 2025 Fall Showcase Fundraiser!
This year’s theme, Coming of Age, explores the moments that shape us — stories of growth, change, and finding our place in the world — all told through the voices and talents of high school students from our Key West community.

Vicki Roush & Laurie Breakwell: Before I Forget...
Still threatening their own brand of trouble, Laurie Breakwell and Vicki Roush storm the Tennessee Williams Cabaret with bold, brassy, and bossy songs. They’ll spark a tear or two with strains both tender and touching. Buckle up, Key West, those Evil Sister Goddesses are back in town and bringing along that uber-talented Jim Rice, not only as Musical Director extraordinaire, but as a not-as-evil singing God(dess) in his own right. Of course, John Neal will be holding court at their ubiquitous on-stage bar.

Ann Hampton Callaway
Ann Hampton Callaway is one of America’s most gifted artists in pop and jazz. A leading champion of the great American Songbook, she’s made her mark as a singer, pianist, composer, lyricist, arranger, actress, educator, TV host and producer. Voted by Broadwayworld.com as “Celebrity of the Year” and two years in a row as “Best Jazz Vocalist,” Ann is a born entertainer. She is best known for Tony-nominated performance in the hit Broadway musical “Swing!” and for writing and singing the theme song to the hit TV series “The Nanny.”

Cello Stories: A Life Under Broadway
With twenty years of Broadway experience, and having performed as a regular member of twenty broadway shows, Mairi explores what it is to be a Broadway musician. Using exquisite arrangements and captivating stories, she illustrated what drew her to a career of supporting a story with music.

Keys Choral Arts: Annual Holiday Concert
Keys Choral Arts, under the Artistic Direction of Timothy Peterson, and accompanied by LouAnn Steely, will present their Annual Holiday Concert on Sunday, December 14th at 4PM in the Tennessee Williams Theatre.

Ulysses Quartet
The Ulysses Quartet has been praised for their "textural versatility," "grave beauty" and "the kind of chemistry many quartets long for, but rarely achieve" (The Strad), as well as their "avid enthusiasm ... with chops to back up their passion" (San Diego Story), "delivered with a blend of exuberance and polished artistry" (The Buffalo News).

Schmaltz & Pepper
Classy klezmer- chamber music and jazz infused with schmaltz
A uniquely virtuosic and entertaining chamber ensemble performing original music inspired by Klezmer, Yiddish Swing, Jazz and Classical music.

Martina Bevis & friends
Prague Conservatory of Music trained guitarist, Martina Bevis, returns to the Tennessee Williams Theatre. Join her along with her special guests to experience music from an artist who has mastered her instrument.

Yevgeny Kutik
With a “dark-hued tone and razor-sharp technique” (The New York Times), violinist Yevgeny Kutik has captivated audiences worldwide with an old-world sound that communicates a modern intellect. Praised for his technical precision and virtuosity, he is lauded for his poetic and imaginative interpretations of standard works as well as rarely heard and newly composed repertoire.

Direct From Sweden: The Music of ABBA
We will give you the closest ABBA experience you’ll ever going to get with some of the most experienced and talented musicians and singers from Sweden in a tribute that will bring you down memory lane through stunning, mirroring images of their stage costumes, hairstyles, and voices.

South Florida Symphony Orchestra: Sibelius’ Symphony No. 2 & Ravel’s Piano Concerto
Rhythmic drive meets lyrical beauty in this exhilarating South Florida Symphony program brimming with wit and brilliance when Ravel’s bluesy and spirited Piano Concerto in G major with SFSO fan-favorite Svetlana Smolina at the keys, joins the windswept glory of Sibelius’ Symphony No. 2. Based on a melody by a 16th century composer, Vaughan Williams’ haunting Fantasia on a Theme by Thomas Tallis opens the sparkling evening of music, led by Key West native, Maestra Sebrina Alfonso.

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.

Dorian Wind Quintet
Recognized by critics, audiences, and colleagues alike for its polished and passionate performances, the Dorian Wind Quintet is known worldwide as one of chamber music’s pre-eminent and longest continuously active ensembles.

Robert Cuccioli
Robert Cuccioli is known by many for his critically acclaimed TONY nominated performance in Jekyll & Hyde, for which he also received the Drama Desk, Outer Critics Circle, and Jeff Awards for “Outstanding Actor in a Musical”. He debuted on Broadway as Inspector Javert in Les Miserables, and last appeared as Dr. Norman Osborn/The Green Goblin in Spider-Man: Turn Off the Dark.

Vienna Boys Choir
The Vienna Boys Choir is one of the most famous choirs in the world, and one of the oldest. Boys have been singing at Vienna's Imperial Chapel since at least 1296. In 1498 Holy Roman Emperor Maximilian I. established a Court Chapel in Vienna where he declared that there were to be boys among the singers, thus laying the foundation for the Vienna Boys Choir.

New York Philharmonic String Quartet
The New York Philharmonic String Quartet comprises four Principal musicians from the Orchestra: Concertmaster Frank Huang (The Charles E. Culpeper Chair); Principal Second Violin Group Qianqian Li; Principal Viola Cynthia Phelps (The Mr. and Mrs. Frederick P. Rose Chair); and Principal Cello Carter Brey (The Fan Fox and Leslie R. Samuels Chair).

Horszowski Trio
Giving performances that are “lithe, persuasive” (The New York Times), “eloquent and enthralling” (The Boston Globe), and described as “the most compelling American group to come on the scene” (The New Yorker), the Horszowski Trio has quickly become a vital force in the international chamber music world since their formation in 2011.

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.

Neil Berg's 50 Years of Rock n' Roll, Part 6
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!

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.

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.

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.

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.

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.

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.

Jazz at Lincoln Center presents Great American Crooners
Soak in the sounds of the velvety melodies and smoky rhythms of quintessential crooners such as Frank Sinatra, Tony Bennett, and Bobby Darin when the golden age of jazz returns with Great American Crooners!

Anne McKee Artists Fund Performance featuring Belle Jampol
Influenced by soul, jazz, and folk, Belle brings a unique blend of musical flavors to her performances.

One Night of Queen
One Night of Queen is a touring 2-hour stage show, paying tribute to the stage theatrics and music of Queen.

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.

Divas Through the Decades: A Celebration of the Lavender Ladies of Music History
Join us for a high-energy concert celebrating iconic women in music through many generations. Featuring powerhouse local vocalists and unforgettable hits, this show brings the evolution of women’s artistry to life. One decade, one diva at a time.

Stomp
Matchboxes, brooms, garbage cans, Zippo lighters, and more fill the stage with energizing beats at STOMP: the inventive and invigorating stage show that’s dance, music, and theatrical performance blended together in one electrifying rhythm.


Hangover Recovery Pool Party
Food & Drinks Specials
Live Music
At the 24 North Pool & Sunset Green Lawn
11am-2pm

ALLEGRO! Series featuring the South Florida Symphony String Quartet
South Florida Symphony Orchestra's String Quartet returns to Little Palm Island for an unforgettable evening of music set against a breathtaking oceanfront backdrop. This exclusive, intimate concert features Mendelssohn’s passionate String Quartet No. 2, Ravel’s elegantly seductive String Quartet in F major, Gardel's beloved tango, Por Una Cabeza, and more.

Celebration of Cuban Music: Centennial Anniversary of San Carlos
CACHAO VIVE!
We are delighted to present a special performance by the Yelsy Heredia Trio featuring a tribute to the legendary Israel López "Cachao" and the captivating sound of Cuban music.

Life, Love, and Key West
Celebrating the art form of "JAZZ" (the musical mirror), through song, dance and film. We go on a musical journey into what's happening now. The good the bad and the funny.

Anders Osborne
Be our guest on the evening of April 23 at 7:30 pm as we welcome back renowned singer, songwriter and virtuoso guitarist Anders Osborne to the storied Monkey Hut at Little Palm Island. This intimate and exclusive performance is only available to a limited number of guests.

Electric Blue Yonder + B.B. Palmer – Live at the Little House
We’re headed back to one of our favorite spots—the world-famous Standard Deluxe—for a special night inside the Little House! The evening kicks off with a set by the one and only B.B. Palmer, with Electric Blue Yonder as his backing band, followed by a full headline set from us to keep the party rolling. To make the night even sweeter... It’s B.B.’s Birthday! Let’s celebrate the man with music, love, and a whole lotta good energy.

Life, Love, and Key West
Celebrating the art form of "JAZZ" (the musical mirror), through song, dance and film. We go on a musical journey into what's happening now. The good the bad and the funny.

Life, Love, and Key West
Celebrating the art form of "JAZZ" (the musical mirror), through song, dance and film. We go on a musical journey into what's happening now. The good the bad and the funny.

Love, The Journey, Acceptance
Join Keys Choral Arts, the Keys premier community chorus, for their spring concert presentation. The chorus presents "Love, The Journey, Acceptance", a beautifully constructed concert under the direction of Timothy Peterson, accompanied by Lou Ann Steely.

The Rat Pack: One More Time!
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.

Life, Love, and Key West
Celebrating the art form of "JAZZ" (the musical mirror), through song, dance and film. We go on a musical journey into what's happening now. The good the bad and the funny.

Key West Historic Days: WOMEN GET THINGS DONE
Camille Toler & Friends will perform on the front porch. Appetizers from our Key West Woman's Club newly revised cookbook will be prepared for you by Key West Cooking School.

Buckets n' Boards in 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!

Paradise Big Band: Holiday II
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.

Darcy Cooke: “Jazz, Cabaret, & Cocktails”
Darcy Cooke presents an intimate evening of 2 parts jazz favorites from the Great American Songbook along with 1 part well-loved cabaret tunes. Called a “swinging jazz singer…displaying versatility and a beautiful voice” by jazz journalist, Scott Yanow, Darcy’s “warm and inviting voice” exudes a depth of emotion that draws in and thrills her audiences.

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

Memories of Coffee
From Johnny Neebo’s Starlight Club, to the Bamboo Room, to the Hukilua, Coffee Butler entertained Key West since 1952. This special performance Memories of Coffee will include the amazing vocals of the King of Key West Soul - Robert Albury, Clayton Lopez and Mina Lopez-Martin, a young new voice of Claire Caplan. They will revive the classic soul sound of the Temptations, Smokey Robinson, and Aretha Franklin along with originals by Coffee Butler. Music Director Larry Baeder will lead the talented Soul of Key West Band.

Catherine Lan and Tao Lin (Duo Beaux Arts)
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.

Les Greene & the Swayzees Concert & Pool Party
Get ready for an afternoon of sun-soaked fun and soulful music for a great cause! Join us for the Les Greene & the Swayzees Concert & Pool Party, a benefit event supporting the victims of the California wildfires.

Life, Love, and Key West
Celebrating the art form of "JAZZ" (the musical mirror), through song, dance and film. We go on a musical journey into what's happening now. The good the bad and the funny.

South Florida Symphony Orchestra: Mozart’s Requiem
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.

Joy in the Cabaret
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.

Poulenc Trio
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.

An Ode to Dennis Pharmacy Brunch featuring Carmen Rodriguez and James King
Take a trip down memory lane with a special brunch honoring the beloved Dennis Pharmacy. Enjoy a menu inspired by its iconic comfort food, accompanied by the soulful sounds of conch singer Carmen Rodriguez and pianist James King.

Life, Love, and Key West
Celebrating the art form of "JAZZ" (the musical mirror), through song, dance and film. We go on a musical journey into what's happening now. The good the bad and the funny.

Martina Bevis in Concert
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.