Waterfront Playhouse - man sits beside green building
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Waterfront Playhouse

4.8
·142 reviews·Key West, United States

Historic Key West venue showcasing world premieres and acclaimed theatrical productions with talented local and visiting artists.

Highlights

Highlights

Must-see attractions

Social content

Social

From TikTok & Reddit

Best Time

Evenings

Live performances await!

CrowdMedium
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Waterfront Playhouse - man sits beside green building

Waterfront Playhouse

Best Time

Evenings

Live performances await!

CrowdMedium
Highlights

Highlights

Must-see attractions

Historic Key West venue showcasing world premieres and acclaimed theatrical productions with talented local and visiting artists.

4.8
(142 reviews)

"It's a wonderful little theater and one of the most unique Key West experiences you can have!"

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TIP

🎯 Book Waterfront Playhouse Tickets Early

Popular shows like 'Margaritaville' and 'Singin' in the Rain' sell out fast. Get your waterfront playhouse tickets in advance!

🚗 Easy Access from Mallory Square

Conveniently located near Mallory Square, making it easy to combine with other Key West attractions.

Third hero image

Highlights

Discover the most iconic attractions and experiences

World Premieres & Acclaimed Productions

World Premieres & Acclaimed Productions

Main Stage

Experience groundbreaking theatrical works and captivating performances in a historic Key West setting.

Historic Venue Charm

Historic Venue Charm

Entire Building

Soak in the atmosphere of a beautifully preserved historic building, adding a unique ambiance to your theater visit.

Talented Local & Visiting Artists

Talented Local & Visiting Artists

Various Performances

Witness the incredible talent of actors and musicians, from local stars to visiting professionals, gracing the stage.

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Planning Your Visit

Book Ahead for Popular Shows

The Waterfront Playhouse hosts acclaimed productions, and tickets for popular shows, especially musicals like 'Margaritaville' or 'Singin' in the Rain,' sell out quickly. Consider booking your waterfront playhouse tickets in advance to secure your preferred seats and avoid disappointment.

Embrace the Intimate Setting

This historic venue offers an intimate theatrical experience. While the seats are cozy, it means you're close to the action. Embrace the close quarters for a truly unique Key West theater experience, perfect for enjoying local talent.

Best Times

When
Evenings
Why
Live performances await!
Crowd
Medium
When
During special events
Why
Unique shows and celebrations
Crowd
High

Insider Tips

from TikTok, Instagram & Reddit

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@blissfullythebensons
504.1K likes • 4.1M views

🎯 Book Waterfront Playhouse Tickets Early

Popular shows like 'Margaritaville' and 'Singin' in the Rain' sell out fast. Get your waterfront playhouse tickets in advance! Reddit

🚗 Easy Access from Mallory Square

Conveniently located near Mallory Square, making it easy to combine with other Key West attractions. Reddit

Splash House, Virginia Beach, Va #757 #thingstodo #sitw #oceanfront #kidfriendly #FamilyFun #paintnight #virginiabeach #datenight #icebreaker #fyp #hamptonroads
@sirpippy
30.4K likes • 710.8K views
📸 reposting @waterfrontplayhouse Richard last month, March27-29/2025 “A Distant Country Called Youth”. “I’m thrilled to be playing Tennessee Williams in Tennessee Williams country, and at the time-honored Waterfront Playhouse! The letters are a beautiful portrait of the self-creation of an artist - Williams’ finding his authentic voice and becoming his true, inimitable self. Of course, the fa...
johnboyrichardthomasfandom
12 likes • 586 views

❄️ Air Conditioning Takes Time

The theater is air-conditioned, but it can take a bit to cool down when full. Be patient! Reddit

🎭 Embrace the Intimate Seating

Seats are cozy! Get ready to meet your neighbor for a unique, close-up theater experience. Reddit

Looky looky! Jammin’ at @hankskeywest with @harderonthefiddle from 5:00-8:00 tonight, then we’re headed to play at the Waterfront Playhouse to celebrate their opening night! I think we play at 10:00? Then I’m off until Monday night! Tootles. #tonybaltimore #keywest #music #letsallgoinsane
tonybaltimoremusic
28 likes • 620 views

Tips

from all over the internet

🎯 Book Waterfront Playhouse Tickets Early

Popular shows like 'Margaritaville' and 'Singin' in the Rain' sell out fast. Get your waterfront playhouse tickets in advance! Reddit

🚗 Easy Access from Mallory Square

Conveniently located near Mallory Square, making it easy to combine with other Key West attractions. Reddit

❄️ Air Conditioning Takes Time

The theater is air-conditioned, but it can take a bit to cool down when full. Be patient! Reddit

🎭 Embrace the Intimate Seating

Seats are cozy! Get ready to meet your neighbor for a unique, close-up theater experience. Reddit

🎶 Opening Night Excitement

Check for opening night celebrations; they often feature live music beforehand! Instagram

What Travellers Say

4.8
(142 reviews)

Reviews Summary

Visitors consistently praise the Waterfront Playhouse for its talented performers and the intimate, charming atmosphere of its historic venue. While the cozy seating might be a tight squeeze for some, the quality of productions like 'La Cage Aux Folles' and 'Singin' in the Rain' makes it a standout Key West experience. The friendly staff and convenient location near Mallory Square add to the positive overall impression.

"Really-really friendly staff. Easy to get to right off Mallory Square. The seats are a little small so be ready to meet your neighbor. I saw Margaritaville the musical. Playhouse is air conditioned, but when if fills up it takes a little but to cool down."

Rob Bobel

"It's a wonderful little theater and one of the most unique key west experiences you can have!"

Josh Averbeck

""La Cage Aux Folles" was TREMENDOUS!!! We are so blessed to have such amazing talent in our town!!!! The Waterfront Playhouse ROCKS!!!!!"

Rude Girl

What People Like

Talented local actors
Intimate venue charm
Quality productions

What People Dislike

Cozy seating

Frequently Asked Questions

🚇 🗺️ Getting There

The Waterfront Playhouse is conveniently located in Key West, easily accessible from Mallory Square. Many visitors find it walkable if staying nearby, or you can opt for local taxis or ride-sharing services. Parking in Key West can be challenging, so consider your transportation options in advance. Reddit

Parking near the Waterfront Playhouse can be limited and is often metered. It's advisable to arrive early if you plan to drive or consider alternative transportation like walking, biking, or using a taxi service. Reddit

Key West has a limited public transport system, but the Conch Tour Train and Old Town Trolley tours often stop near Mallory Square, which is close to the playhouse. Check their routes for convenience. Reddit

🎫 🎫 Tickets & Entry

You can purchase waterfront playhouse tickets directly from the Waterfront Playhouse website or at their box office. For popular shows, booking in advance is highly recommended to secure your seats. Reddit

Showtimes usually vary, but evening performances are common, often starting around 7:00 PM or 8:00 PM. Some matinee performances may also be available. Check the specific show's schedule for exact times. Instagram

Discounts may be available for students, seniors, or military personnel. It's best to check the official Waterfront Playhouse website or contact the box office directly for current discount information. Reddit

Policies can vary, but generally, tickets are non-refundable. Exchanges might be possible for a fee, depending on availability and the specific show. Contact the box office for details. Reddit

While possible, it's not recommended for popular shows as they often sell out. If available, tickets can be purchased at the box office on the day of the performance. Reddit

🎫 🎭 Onsite Experience

The Waterfront Playhouse offers an intimate seating arrangement. While the seats are cozy, this setup brings you closer to the performance, enhancing the overall theater experience. Reddit

Yes, the Waterfront Playhouse is air-conditioned. However, it may take some time to cool down the entire venue, especially when it's full. Reddit

You can expect a diverse range of productions, including theatrical world premieres, musicals like 'Margaritaville' and 'Singin' in the Rain,' and even audience-participation shows like 'Rocky Horror Picture Show.' InstagramReddit

The historic nature of the building may present some accessibility challenges. It's recommended to contact the box office in advance to discuss specific needs and available accommodations. Reddit

Generally, photography and videography are not permitted during performances to avoid disturbing the actors and other audience members. Check with the venue for their specific policy. TikTok

🍽️ 🍽️ Food & Dining

The Waterfront Playhouse itself does not typically offer full dining services. However, its prime location in Key West means there are numerous restaurants and bars nearby, especially around Mallory Square, perfect for a pre or post-show meal. Reddit

Outside food and beverages are usually not permitted inside the theater. There might be a concession stand for snacks and drinks, but it's best to confirm this with the venue. Reddit

The area around Mallory Square and Duval Street offers a wide array of dining options, from casual seafood shacks to upscale restaurants. You can find everything from Cuban cuisine to fresh Key West specialties. Reddit

📸 📸 Photography

The historic architecture of the building itself offers great photo opportunities. You can capture the exterior charm and perhaps some shots of the interior before the show begins. Instagram

Photography of the stage and performances is typically prohibited during the show to respect the performers and audience. Always check the venue's policy before taking pictures. TikTok

For Different Travelers

Tailored advice for your travel style

👨‍👩‍👧 Families with Kids

While the Waterfront Playhouse primarily focuses on adult-oriented theater, certain productions might be suitable for older children or teenagers. Shows like 'Rocky Horror Picture Show' are known for audience participation, which can be fun for a more adventurous family outing. Reddit It's always best to check the specific show's content and age recommendations before booking tickets. The intimate setting can be engaging for younger audiences, but ensure the themes align with your family's preferences. TikTok

🎶 Music Lovers

The Waterfront Playhouse occasionally hosts musicals and performances that heavily feature music, such as 'Margaritaville' and 'Singin' in the Rain.' Reddit You might also catch opening night celebrations that include live music performances before the show, as seen with local musicians heading to the playhouse after a set. Instagram Keep an eye on their schedule for musical theater productions and special musical events. Instagram

🎭 Theater Enthusiasts

For dedicated theater fans, the Waterfront Playhouse is a must-visit. Its reputation for world premieres and high-quality productions means you're likely to see something new and exciting. Instagram The intimate venue provides a unique perspective on performances, allowing you to appreciate the nuances of acting and staging. Don't miss the chance to experience the vibrant local theater scene in Key West. Reddit

Deep Dives

In-depth insights and expert knowledge

The Magic of Live Theater in Key West

The Waterfront Playhouse is more than just a venue; it's a cornerstone of Key West's vibrant arts scene. Housed in a historic building, it offers an intimate and engaging theatrical experience that draws both locals and tourists. The playhouse is renowned for staging world premieres and critically acclaimed productions, showcasing the incredible talent that thrives in this unique island city. From musicals that fill the stage with energy to thought-provoking dramas, each performance is crafted with passion and precision. InstagramReddit

Visitors often rave about the quality of the performances and the dedication of the actors, many of whom are local talents or visiting professionals. The close proximity of the seating means you're never far from the action, creating a truly immersive atmosphere. It's this blend of artistic excellence and the charming, historic setting that makes a visit to the Waterfront Playhouse a memorable part of any Key West itinerary. Reddit

Beyond the main stage productions, the playhouse sometimes hosts special events and collaborations, like the opening night celebrations mentioned by musicians. These events further cement its role as a cultural hub. Whether you're a seasoned theatergoer or new to the stage, the Waterfront Playhouse promises a delightful and enriching experience. Instagram

Navigating the Waterfront Playhouse Experience

Planning your visit to the Waterfront Playhouse is straightforward, but a few tips can enhance your experience. Booking waterfront playhouse tickets in advance is highly recommended, especially for popular shows like 'Margaritaville' or 'Singin' in the Rain,' as they tend to sell out quickly. Reddit The venue's location near Mallory Square makes it incredibly convenient to access, allowing you to easily combine your theater visit with other Key West attractions. Reddit

When you arrive, be prepared for the intimate seating arrangement. While the seats are cozy, this design ensures you have a fantastic view of the stage and feel connected to the performance. The playhouse is air-conditioned, but it might take a little while to reach optimal coolness once the audience fills the space, so a bit of patience is key. Reddit The friendly staff and the overall welcoming atmosphere contribute to making your visit comfortable and enjoyable. Reddit

For those driving, parking can be a challenge in Key West. It's advisable to arrive early if you plan to park nearby, or consider alternative transportation options such as taxis, ride-sharing services, or even walking if you're staying in the vicinity. This proactive approach will help ensure a stress-free arrival for your waterfront playhouse theater experience. Reddit

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