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
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.
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.
291 Front St suite 207
(305) 294-2665
https://www.keywestcookingshow.com/
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.
711 Duval Street
(305) 294-0555
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.
801 Duval Street
(305) 294-4737
The Birdcage Starring Christopher Peterson
The Birdcage Cabaret offers a slightly more theatrical, cabaret-style drag experience focused on performance, storytelling, and wit. Acts feel thoughtfully staged, mixing humor, music, and moments of genuine showmanship. The vibe is energetic but more intimate, making it easy to stay locked into the performance from start to finish. It’s an excellent option if you enjoy drag with a bit more narrative and nuance.
711 Duval Street
(305) 294-0555
https://aquakeywest.com/the-birdcage-cabaret