Inside Key West Arts and Culture

Although Key West is a tiny city, it is home to a large creative community and a strong arts and culture scene. The good weather and beautiful environment of Key West has always drawn talented people, from Tennessee Williams and Ernest Hemingway to Jimmy Buffet and a host of other celebrities, artists, and performers. The island still offers residents and visitors alike many good opportunities to enjoy artistic work, including the dramatic productions of several community theater groups that feature a talent pool of skilled locals augmented by visiting professionals from New York and Los Angeles who come to Key West for a tropical break. If you would like to plan an evening of theatre in Key West, there are two venues in particular that will combine a taste of Key West history with easy access to live productions ranging across the spectrum of genres.

The Waterfront Playhouse

The Waterfront Playhouse has been the home of one of Key West’s original theater groups, the Key West players, since 1960. The Players, a group initially composed of locals and Navy personnel stationed in Key West during World War II, had been putting on productions in any space available, including the original 1829 carriage house that later became the Red Barn Theatre, and the U.S.S. Gilmore, a Fulton-class submarine tender that was stationed in Key West during WW II.

Searching for a permanent home, the Key West Players came across a decrepit 1880’s-era ice warehouse located on historic Mallory Square, and were aided by member Tennessee Williams in securing the property. After a complete renovation, the warehouse became the theatre home that the Players enjoy to this day. As Key West’s oldest continuously running theatre, the Waterfront Playhouse operates as a not-for-profit professional theatre that seats 150 audience members and offers a wide range of concerts, comedies, dramas, musicals, and world premieres.

The Playhouse has recently undergone several upgrades including the addition of a new lobby, new lighting and sound, and the dedication of a new stage. If you are looking to enjoy an exciting evening of high-quality theatre, perhaps after enjoying the sunset celebration on Mallory Square, grab some tickets for a production at the Waterfront Playhouse.

The Red Barn Theatre

What is now the Red barn Theatre was originally an 1829-vintage carriage house on Duval Street in old Key West. When automobiles came to Key West and carriages became obsolete, the building was adopted by the Key West Players soon after the group’s initial formation during WW II. When the Players moved to the Mallory Square Waterfront Playhouse in 1960, the old carriage house theatre sat empty until it was revived as a puppet theatre by Key West residents Ruth Guttman and her husband Yehuda. The Guttman’s presented many wonderful puppet shows there throughout the 1970s, along with concerts performed by Yehuda, who was a gifted pianist.

The carriage house officially become the Red Barn Theatre in 1980, when it was renovated and reopened by a group of actors and technicians working under the incorporated name of the Red Barn Actors Studio. Since then, theatre lovers from the Key West community and beyond have provided the support needed to keep the Red Barn thriving. In 2002, a $660,000 renovation gave the Red Barn permanent rehearsal hall space, costume storage, dressing rooms, a scenery shop, new restrooms, and a box office.

Many members of the Key West community contributed to the renovation efforts, and when the work was completed, architect Michael Miller’s design and Deal Builders’ quality construction won the Red Barn the prestigious Historic Preservation Award and a Star of Excellence for new construction from the Historic Florida Keys Foundation in 2004.

The Red Barn Theatre is a Key West cultural mainstay where you can enjoy an excellent evening of theatre put on in one of the city’s most well known historic buildings. Drop by the Red Barn to see a play during your Key West visit, and join the many celebrities and talented individuals who have been part of the history of this nationally-recognized community theatre.

 

Read More
  • Key West Sail, Snorkel, Kayak with Sunset Option
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out

    Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

     4.5 or 6.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $99
    $90
    $99
    $90
  • Key West Backcountry Safari
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out

    Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....

     4.5 or 6.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $120
    $99
    $120
    $99
  • Key West 4-Seater Gas Powered Golf Cart Rental
    Likely to Sell Out
    Likely to Sell Out

    Considering a golf cart rental in Key West? Four adults can zip around the island in style on a 4-seater gas-powered EZGO golf cart, and...

     3 hours and up  Hotel pickup offered  Free Cancellation  Instant Confirmation
    Best Rate
    $90
    Best Rate
    $90
  • Key West 8-Seater Gas Powered Golf Cart Rental
    Likely to Sell Out
    Likely to Sell Out

    In Key West for a wedding or other family event? Got a large group of cruise ship friends who want to see all of the...

     3 hours and up  Hotel pickup offered  Free Cancellation  Instant Confirmation
    Best Rate
    $200
    Best Rate
    $200
  • Key West 6 Seater Gas Powered Golf Cart Rental

    Need a Key West golf cart rental that can get a group of six around the island in fun style? A 6-seater gas-engine EZGO Express...

     3 hours and up  Hotel pickup offered  Free Cancellation  Instant Confirmation
    Best Rate
    $170
    Best Rate
    $170
  • Key West Split Fishing Charter
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out

    On a Key West Split Fishing Charter, you save by dividing the charter cost between several people. Book your Key West split-charter fishing trip now...

     4 or 6 hours (approx.)  Free Cancellation
    $350
    $200
    $350
    $200
  • Key West Snuba® (No Dive Certification Required)

    If you want to go beyond snorkeling and experience the world's underwater beauty in the safest and easiest way possible, try Snuba®!...

     3 hours 30 minutes  Instant Confirmation
    from
    $160
    from
    $160
  • Key West Deep Sea Fishing Charter
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out

    Experience the thrill of a Key West deep sea fishing adventure on a hunt for trophy game fish with your own Key West fishing charter...

     4, 6 or 8 hours (approx.)  Free Cancellation
    $1,000
    $900
    $1,000
    $900
  • Key West Dolphin Watch & Snorkel
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

    Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins....

     3 hours 30 minutes (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    Best Rate
    $99
    Best Rate
    $99
  • Miami to Key West Day Trip with Snorkeling
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out

    Take a luxury coach tour from Miami to Key West then cruise out on the emerald waters to enjoy a Key West snorkeling trip on...

     6 hours in Key West (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    $169
    $119
    $169
    $119
  • Key West Party Boat Fishing Charter

    Our Key West Party Boat Fishing Charter is great for an affordable day on the water with friends and family enjoying the best Key West...

     6 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $69.69
    Best Rate
    $69.69
Filter
Language
Currency

Site Settings

Activity name

Currency

Activity name

Sorting, ranking, and search results

Activity name

Inside Key West wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Inside Key West over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

Cool Rewards Terms & Conditions

Activity name

Cool Rewards

  • Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

Earning rewards

  • Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
  • Earned rewards will be issued in a pending state and will move to a confirmed state 24 hours after the start time of the experience.
  • Earned rewards will be available to redeem once they are no longer in a pending state.
  • For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
  • If a booking where rewards were issued is canceled, the earned rewards will not be redeemable and will be moved to a canceled state.

Redeeming rewards

  • To redeem rewards, you must be logged into your Cool Destinations account.
  • Any available rewards will be automatically applied the next time you make a booking, and their value will be deducted from your order at checkout, unless you choose not to apply them, which requires you to indicate this via the toggle switch. Bookings made using rewards are subject to the standard Cool Destinations Customer Terms of Use.
  • You will not be able to redeem only a portion of your available rewards at checkout. It is only possible to redeem all or none of your available rewards.
  • There is no minimum order value required to redeem your rewards. This means that you can pay for 100% of your order with rewards.
  • Rewards are non-transferable and cannot be redeemed for cash.
  • If rewards are redeemed against a booking that is canceled or refunded, the rewards will be reissued to your account.

Miscellaneous

  • You can check your Cool Destinations account to see the rewards you have collected at any time. You are responsible for ensuring that your rewards balance is correct.
  • We reserve the right to modify these Cool Rewards Terms and Conditions at any time, with or without notice, including the rules for earning and redeeming rewards. Any changes will be reflected in the updated Terms and Conditions.
  • We reserve the right to terminate the Cool Rewards program and cease issuing any further rewards on future bookings. All pending and available rewards balances will be honored.
  • By earning and redeeming rewards, you agree to these Terms and Conditions, as well as any subsequent changes made to them.