Discover Key West

Island Entertainment

Entertainment in Key West takes many forms, and part of its appeal is that it resists being defined by a single style. Some evenings are shaped by theater, storytelling, or hands-on experiences that invite you to learn something new, while others lean into performances that are playful, bold, and comfortably irreverent. What draws me in is when an experience feels well considered and true to the island’s personality.

It doesn’t need to be wild, and it doesn’t need to be refined. What matters is intention and a sense that it’s meant to be enjoyed. The selections here reflect that range, from theaters and cooking classes to live music, long-running shows, and adult entertainment that speaks to Key West’s creative, anything-goes spirit.

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

www.waterfrontplayhouse.org

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

www.redbarntheater.com

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.

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

https://aquakeywest.com/aqua

Aqua Details & Booking

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

https://801.bar/801-girls

801 Early Show (9pm)

801 Late Show (11pm)

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.