Exploring The Key West Theater Scene

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The spotlight is usually on the talent and the shows however today we are setting the stage and getting to know the theater scene in Key West. So many plays so little time and on top of it all there is a little bit of history to top it off.  Let’s go theater hopping and explore the Key West Theater Scene!

Waterfront Playhouse

Florida Monthly Magazine named Waterfront Playhouse “The Best Professional Theater in Florida,” and judging by the 2017 schedule expect just that and a jam packed schedule with comedies, dramas and musicals.

Jan. 24 – Feb. 11 “The Trip to Bountiful”

Feb. 28 – March 25 “Avenue Q”

April 12 – 29 “Good People”

May 10 – 27 “Forever Plaid”

Waterfront playhouse

Good to Know: Every Tuesday (Jan 10 – March 21) at 6:30pm head over to Aqua Nightclub for Aqua Idol, a benefit for the Waterfront Playhouse.  This is where you will see our local friends with great talent sing out their hearts to raise money for the theater.  Some have great talent and others think they have great talent -if you’ve seen American Idol then you will understand. So if you are visiting on a Tuesday head over to Aqua and enjoy a night of fun for a great cause. Admission is free.


History: The Waterfront Playhouse began in 1939 where the original producing organization was called the Key West Players, which included locals and navy personnel.  In 1960 the permanent home of Waterfront Playhouse was found with the help of Key West Player Tennessee Williams. The warehouse was totally renovated (the building is a converted ice house from the 1880’s, and the original sweeping stone walls still stand) and transformed into The Waterfront Playhouse (the term by which The Key West Players is most widely known today.)


The Waterfront Playhouse is a non-profit professional theater with 150 intimate seats located steps from the Key West Sunset Celebration at Mallory Square. When the sun sets the curtain rises.  To purchase tickets and learn more about the 2017 Waterfront Playhouse, click here.


Waterfront Playhouse
310 Wall Street


Red Barn Theater

Located on the world famous Duval Street and celebrating 37 years of professional theater in Key West is the Red Barn Theater. Big things come in small spaces and at the Red Barn Theater that says it all.  It’s a cultural cornerstone for the Key West community while building a national reputation for creating BIG things in a small space.  This small quaint theater has 88 seats so get your tickets early, don’t worry about getting a bad seat (there really is no such thing) and sit back, relax and enjoy the show.


2017 Red Barn Theatre Schedule:

Jan 20 – Feb. 12 “Murder for Two” Musical Comedy

Feb. 21 – March 18 “I Do I Do” This endearing musical spans the years of 1895 to 1945, rolling out one catchy song after another in this bedroom comedy.

Feb. 26 – Feb. 27 “Still The Old Class Clown, Just A Lot Older” A Stand-Up Evening of Comedy starring Gerri Louise Gates. TWO NIGHTS ONLY!

March 28 – April 15 “Camping with Henry & Tom” Bristling with humor, this delightful play is fictionally based on a 1921 camping trip taken by Henry Ford, Thomas Edison, and President Warren G. Harding.

April 25 – May 13 “Short Attention Span Theatre” An evening of short 10-minute plays including lots of laughs and incredible talent.

Red barn


History: This 88-seat theater is a converted carriage house built behind the Duval Street mansion in 1829.  Many well-known and very talented people are a part of the Red Barn Theatre’s story. Richard Wilbur, the former U.S. Poet Laureate, worked with the Red Barn to produce his Moliere translations and Shel Silverstein, the gifted children’s writer, gave the Red Barn carte blanche to produce many of his very grown-up plays. Jimmy Buffett, Philip Burton, Terrence McNally, Jerry Herman, and Tennessee Williams have all made the Red Barn a part of their cultural experiences in Key West.

Since there are only 88 seats at the Red Barn we suggest you don’t wait…get your tickets now!

Red Barn Theatre
319 Duval Street

Tennessee Williams Theatre

tenn williams


Located at the Florida Keys Community College you will find a 480-seat theatre, the Tennessee Williams Theatre. National tours, local productions, concerts, symphonies and cabarets are on schedule to entertain you while visiting the Florida Keys.  In addition to award-winning musicals and plays like Pippin, it also features entertainers like The Spinners, Art Garfunkel, Neil Berg’s 105 Years of Broadway, The Carpenters – A Tribute Concert, Dance Tours, Local Artists and Symphonies just to name a few.   There is also a grand foyer performance area for smaller intimate events and concerts.


Local performers also take to the stage for cabaret events and special performances.  Here are two upcoming events worth listening to:


Bobby Nesbitt & Carmen Rodriguez in “Salute to the USO” – February 12-13 & 19-20, 2017 at 8pm

The Harry S. Truman Little White House is pleased to announce “Salute to the USO” to benefit the Foundation while honoring military service members. Singer and pianist Bobby Nesbitt along with singer Carmen Rodriguez will entertain you with popular songs as they educate you on the significance of the song selection as well as entertainers that made them great.


Randy Roberts 2017 Valentine’s Cabaret

Celebrate Valentine’s Day with Key West favorite Randy Roberts in an evening of love-themed songs, clever repartee and more! Audiences who are already fans of Randy’s remarkable talent will tell you that this is cabaret at its finest.


As you can see, this venue brings local, national and international talent to the stage in Key West. To stay on top of what’s happening at Tennessee Williams Theater make sure to check view the calendar of events and performances at


Tennessee Williams Theatre
5901 College Road, Key West

Key West Theater

New to Key West is the Key West Theatre. It sounds funny to say the Key West Theater is new but it really is a newly renovated performing arts center that presents original plays, musicals, films, concerts and more.


What you can expect to see – or should we say whom you can expect to see is top tier music, concerts, theatrical productions, comedy & variety specials and locally produced Key West events. They have a very impressive performance schedule and they continue to update on a daily basis.  Here are a few of the shows scheduled for the next few months:

Key West theatre

Puddles Pity Party – February

“Puddles gives an emotive performance that resonates with all kinds of folks,” says Geier. “The crowd really responds to him. There’s something about a giant sad singing clown that comforts us, let’s us know it’s ok to feel, to show our feelings. It’s a sad and beautiful world, and we’re all in it together, even when we’re totally alone.


Southern Rock Legends “The Outlaws” – Feb 12

Southside Johnny & the Asbury Jukes – Feb 21

With a decades-long successful career, Southside Johnny and the Asbury Jukes continue to deliver their soul-searing brand of raucous blues and R&B, with material mined from their many albums, featuring hits like “I Don’t Want To Go Home”, “Love On The Wrong Side Of Town”, “The Fever”, “This Time It’s For Real”, “Talk To Me” and their definitive fun-time cover of “We’re Having A Party”. The Jukes’ legendary high-energy live performances always satisfy with their classic blend of Stax-influenced R&B and gritty, Stonesy rock and roll.

Alan Cumming – March

Time Magazine named him one of the most fun people in show business. He’s a Tony Award winner and has had Golden Globe, Emmy, SAG and Satellite award nominations. Alan Cumming will be performing at the Key West Theater on March 1st and 2nd.

The Local Scene at the Key West Theater

The stage is set for a variety of local performances from musicals to the Sunday Ramble to short plays and performances, what you can expect to see is a variety of talent and the best of Key West

129 Miles from Walmart (Performances in February and March)

Did you know that Key West is about 129 miles away from the nearest Walmart? That is just one of the many reasons life in the Keys is not like anywhere else in the country. This inspired evening of one-acts includes original short plays by some of Key West’s best, and celebrates those who are living their lives a bit differently than most.


Good to Know: Key West Theater offers a full bar with cocktail table service!


Key West Theater
512 Eaton Street


We’ve set the stage and invite you to take the next step and enjoy one or more of the many upcoming performances during your trip to Key West. We’ll see you at the Theater!


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