Theater & Concerts
Waterfront Playhouse
Located near Mallory Square, this historic theater has been staging plays for decades and is widely regarded as the island’s premier live theater. Productions are consistently polished and well-cast, often rivaling what you’d expect in much larger cities. Locals appreciate the focus on strong storytelling—dramas, comedies, and contemporary works—in an intimate setting where the audience is truly engaged. Local tip: shows often sell out during peak season, so if something catches your interest, book early.
407 Wall Street
(305) 294-5015
Red Barn Theater
This intimate venue consistently delivers high-quality live entertainment, with genuinely good sightlines from every seat. The calendar includes national touring acts, tribute shows, comedy, music, and limited-run performances, all in a comfortable, air-conditioned space. It feels polished without being stuffy and lively without ever becoming chaotic. Local tip: check the calendar early—many shows sell out, especially during peak season.
319 Duval Street
(305) 296-9911
Coffee Butler Amphitheater
A few blocks from Duval Street, this intimate outdoor venue consistently delivers high-quality live entertainment in a space where there truly isn’t a bad seat. The calendar features national touring acts, tribute shows, comedy, music, and limited-run performances, all in a comfortable, air-conditioned setting. It feels polished without being stuffy and lively without ever becoming chaotic. Local tip: check the calendar early—many shows sell out, especially during peak season.
21 Quay Road
(305) 985-0433
https://www.thekeywestamp.com/
Key West Theater
Tucked just off Duval Street, this intimate venue consistently delivers high-quality live entertainment in a space where there truly isn’t a bad seat. The calendar features national touring acts, tribute shows, comedy, music, and limited-run performances, all in a comfortable, air-conditioned setting. It feels polished without being stuffy and lively without ever becoming chaotic. Local tip: check the calendar early—many shows sell out, especially during peak season.
512 Eaton St
(305) 985-0433
https://thekeywesttheater.com/
Key West Cooking School
The cooking show at the Key West Cooking School blends live chef demonstrations with the real culinary history of the island. Dishes are prepared in front of you and served as the show unfolds, creating a relaxed, immersive experience. The storytelling goes beyond tourist trivia, the cocktails are well made, and the food is genuinely very good. It’s a great alternative to a traditional restaurant night and works equally well for lunch or dinner.
Drag Shows
Aqua Plex featuring the Aquanettes
AquaPlex’s signature show delivers high-energy drag performances with big vocals, bold costumes, and plenty of personality. The Aquanettes blend polished production with playful humor in a way that feels celebratory rather than over-the-top. The room stays lively and engaged, with strong crowd interaction and a party-forward atmosphere. It’s a great choice if you want classic Key West fun done well and without taking itself too seriously.
The 801 Girls
The drag show at 801 Bourbon Bar is high-energy, fast-paced, and unapologetically fun. Performances lean bold and interactive, with crowd engagement that keeps the room lively from start to finish. It’s casual, loud, and very much a Duval Street experience rather than a sit-back-and-watch theater show. If you’re looking for drag that feels spontaneous, social, and a little wild, this is the place.
The Birdcage Starring Christopher Peterson
For over three decades, Christopher Peterson has been one of Key West’s most celebrated entertainers, known for dazzling live vocals, razor-sharp comedy, and unforgettable celebrity impersonations. At The Birdcage Cabaret, Peterson brings his signature style to a fully immersive cabaret experience featuring live singing, iconic characters, stunning costumes, and the talented Aquanettes in a high-energy variety production. Inspired by the glamour of classic showrooms with a modern Key West spirit, The Birdcage delivers a night of entertainment where every performance feels larger than life.
Randy Roberts Live!
Experience the award-winning Randy Roberts LIVE - a Key West tradition blending world-class entertainment, sharp comedy, dazzling costumes, and powerhouse live vocals. Known for unforgettable performances inspired by icons like Cher, Bette Midler, and Liza Minnelli, Randy brings a Vegas-meets-Broadway energy to the Crystal Room for a night of glamour, laughter, and pure showmanship you won't forget.