Fringe Theater Key West has been bringing unexpected drama, laughs, and community-centered performances to life since 2009. Originally called The People’s Theater (because, you know, it’s for the people), this little gem has become a go-to spot for community-centered, inclusive theater. Fringe lives by its motto: “Expect the Unexpected,” and you can expect that with original works that’ll make you laugh, cry, or both. That’s the magic of Fringe.

For over 40 years, the Tennessee Williams Theatre has been Key West’s cultural hotspot, blending Broadway flair with island vibes. Partnering with the College of the Florida Keys, this nonprofit hosts everything from national tours to world premieres that’ll blow you away. Known for its strong ties to the LGBTQ+ community, it’s also home to some of the island’s most fabulous events. If you love a great show, make this iconic theater a must-see on your Key West trip!

Looking for the perfect spot to vibe out with live music and killer views? Welcome to the Coffee Butler Amphitheater in Key West—where the Gulf of Mexico serves as your backdrop, and the vibes are as warm as the Florida sun. Nestled in Truman Waterfront (fancy, right?), this outdoor gem has it all: a grassy general admission lawn for the barefoot crowd and cozy reserved seating for those who like to keep it classy. Oh, and heads up—this is an open-air venue, so you’re at the mercy of Key West’s mood swings. Sun, rain, wind—you name it. Pack your poncho, slap on some sunscreen, and maybe bring a hat that won’t blow away. Trust us, no one wants to go viral for chasing their hat across the lawn mid-concert.

The Red Barn Theatre is a hidden treasure in Key West, known for its Broadway-caliber productions and rich legacy of working with legends like Tennessee Williams, Terrence McNally, and Shel Silverstein. Each season, this intimate venue delivers smart, high-quality theater—including the wildly popular Short Attention Span Theatre, a fast-paced evening of short plays often featuring queer themes and local comedic talent. Whether you’re a theater buff or just looking for a fun, thought-provoking night out, the Red Barn never disappoints.

The Key West Theater is a beloved cultural hotspot where music, comedy, and live performance take center stage—often with a fabulous queer twist. Housed in a beautifully restored former church, this intimate venue regularly features LGBTQ+ performers, drag shows, and queer artists from around the country. Whether you’re catching a live concert, laughing through a stand-up set, or soaking up a thought-provoking film, the vibe is always welcoming, creative, and a little bit camp. For a night out that celebrates diversity and talent, the Key West Theater delivers.

The Tropic Cinema is Key West’s indie film paradise. Since 2004, this nonprofit has brought independent, international, queer, and classic films to the island. With its charming Art Deco marquee, cozy screening rooms, and a concession stand offering buttery popcorn with island-famous seasonings, Zabar’s coffee, and wine, it’s a movie lover’s dream. The Tropic is also a cultural hub, hosting concerts, lectures, and visits from legends like John Waters. It’s where queer cinema meets community in the heart of the Keys.

The Waterfront Playhouse: where history meets drama, and we’re not just talking about the plot twists! Nestled in Key West’s iconic Mallory Square, this legendary not-for-profit theater has been serving up bold, professional productions for over 80 years. And let’s just say, it’s not your average community stage. They mix local talent with fabulous queer performers straight from Broadway, bringing big-city flair to an intimate 150-seat venue. Oh, and did we mention it’s just steps away from that famous sunset celebration?