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Address: 312 Wall St., Mallory Square, Key West, FL 33040
Phone Number:
+1 305-294-5015

Named "The Best Professional Theater in Florida" (Florida Monthly...

Named "The Best Professional Theater in Florida" (Florida Monthly Magazine), The Waterfront Playhouse is a not-for-profit, professional theater located on historic Mallory Square in Old Town Key West that attracts locals and tourists alike with a wide range of comedies, dramas, musicals, concerts, and world premieres. Recent hit productions at the Playhouse include "The Drowsy Chaperone," "The 39 Steps," "August: Osage County," Dirty Rotten Scoundrels," "Glengarry Glen Ross," "Lend Me a Tenor," "Doubt," "Twelve Angry Men," "The Full Monty," "Reefer Madness," "Urinetown," "Equus" and the world premiere of Hy Conrad's "Home Exchange." Join us for an exciting evening of theater in Paradise. When the sun sets, the curtain rises at The Waterfront Playhouse.

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TripAdvisor Reviewer Highlights

Read all 203 reviews
Visitor rating
  • 169
  • 22
    Very good
  • 5
  • 1
  • 2

Fantastic performance of Drowsy Chaperone. SOme of the best theatre we have seen anywhere and not too expensive. If you have a few hours free in the evening to see a show AND if... read more

5 of 5 bubblesReviewed 2 April 2013
Donna R
Springfield, Virginia
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203 Reviews from our TripAdvisor Community

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Showing 199: English reviews
Springfield, Virginia
Level Contributor
41 reviews
17 attraction reviews
common_n_attraction_reviews_1bd8 15 helpful votes
5 of 5 bubbles Reviewed 2 April 2013

Fantastic performance of Drowsy Chaperone. SOme of the best theatre we have seen anywhere and not too expensive. If you have a few hours free in the evening to see a show AND if you are lucky enough to get tickets, it's a must see. Talent is superb. Theatre is a short walk from most places and near Mallory Square.... More 

Thank Donna R
Port Washington, New York
2 reviews
5 of 5 bubbles Reviewed 26 March 2013

We recently celebrated our 35th anniversary in Key West and saw the Drowsy Chaperone at the Waterfront Playhouse. We had a great time! We loved the singing, dancing and laughing. All the better served in an intimate theater where every seat is a good seat. If you are in Key West don't miss it since it is a first rate... More 

Thank Fred Z
Paris, France
Level Contributor
94 reviews
56 attraction reviews
common_n_attraction_reviews_1bd8 54 helpful votes
3 of 5 bubbles Reviewed 23 March 2013

Waterfront Playhouse excellent venue intimate. Good sound all seats unobstructed. Almost all shows have an edge to them and many will feel put off by course language, rough subject matter and adult "humor".

2 Thank waldokw
Jeff J, Manager at Waterfront Playhouse, responded to this review

We're so sorry that you were unhappy with the content of the show. This season's productions (so far) were "The 39 Steps," "Six Dance Lessons in Six Weeks," and "The Drowsy Chaperone" -- all very popular Broadway hits with very mild/PG language. If you did find anything offensive, please let me know so that I can tell you, in advance,... More 

Key West, Florida
Level Contributor
9 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
5 of 5 bubbles Reviewed 20 March 2013

Currently showing at the Waterfront Playhouse is the comedy and musical, The Drowsy Chaperone. Everything about this show is super - the direction, the cast, the stage setting and the integration of lights and sound with the performance are just super!!! All 18 performers are perfectly suited for their roles - all are so good that you start to say... More 

2 Thank jpaul1945
New York City, New York
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed 18 March 2013

I visit Key West annually during the winter months. I'm from New York. As an avid theater goer I can't say enough about the productions The Waterfront Playhouse puts forth, a big bravo !! I just saw The Drowsy Chaperone. Cast, sets, singing, dancing, music, all so well done in this most charming of theaters. ( I actually enjoyed it... More 

Thank travelbuff53
Key West, Florida
Level Contributor
7 reviews
common_n_attraction_reviews_1bd8 12 helpful votes
5 of 5 bubbles Reviewed 18 March 2013

Charming theater, professional actors. Wonderful quality production of this musical comedy! Perfect spot to step away from some of the Mallory Square craziness.

1 Thank Chris B
Allegany, New York
Level Contributor
72 reviews
28 attraction reviews
common_n_attraction_reviews_1bd8 23 helpful votes
5 of 5 bubbles Reviewed 17 March 2013

Not too big, not too small, just right for enjoying a preview of a fun musical "The Drowsy Chaperone" with a great cast that included our son! Homey, comfortable, centrally located. Fun!

1 Thank sjasis
New Hope, Pennsylvania
Level Contributor
6 reviews
5 of 5 bubbles Reviewed 15 March 2013

I just saw "The Drowsy Chaperone" and what a show! Amazing cast, brilliant staging, fabulous costumes. Danny Weathers was perfect as the Man in the Chair. DO NOT MISS THIS SHOW!

Thank Rob N
Hamilton, Ontario, Canada
Level Contributor
12 reviews
common_n_attraction_reviews_1bd8 9 helpful votes
4 of 5 bubbles Reviewed 15 March 2013

We took in a performance of "The Drousy Chaperone" and it was well done and very entertaining! Cast was great especially Adolpho!

Thank chief0099
Key West, Florida
Level Contributor
132 reviews
16 attraction reviews
common_n_attraction_reviews_1bd8 82 helpful votes
5 of 5 bubbles Reviewed 14 March 2013

Everytime we have gone or we have treated guests we've always had a great time... I saw one person said this theater was terrible... I would like to meet that person, so if you would email me I would like to talk to your Doctors... Enjoy and support our local Key West Theater ! Cheers

Thank Margeritavile

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