Please confirm details with the event organizers or venues in the event of changes or cancellations.
Key West
ONGOING
Randy Roberts Live!
Key West: Spotlighted on television’s hit series “America’s Got Talent,” Randy Roberts shines in this live, multi-media tribute to some of the world’s most beloved performers. His uncanny impersonations of Cher, Bette Midler, and Mae West are spot-on. Randy will have you rolling in the aisles when he performs a titillating striptease as the bawdy Gypsy Rose Lee. Catch this fantastic show at La Te Da’s Crystal Room Cabaret, 1125 Duval St. Tickets & info: 305-296-6706; lateda.com.
Nightly
The Birdcage Cabaret
Key West: Home of North America’s foremost female impressionist, Christopher Peterson, and Key West’s famous drag queens, The Aquanettes.. The Aquanettes also perform separately on M – Tu at 9 pm with two shows on W – Su at 7 and 9 pm. The bar is open Su – Th from 2 pm – 2 am and F – Sa from 2 pm – 4 am. The all-day Happy Hour doesn’t stop until showtime. It all takes place at the Birdcage Cabaret at 504 Angela St in the Aquaplex. Info: 305-294-0555; aquakeywest.com.
The Aquanettes
Key West: Key West’s talented female impressionist troupe transforms into a bevy of beauties using elaborate costuming, makeup, and lip-sync. Renowned for its outrageous and comic numbers, this adult-oriented, interactive show is one of Key West’s most popular shows. Takes place on M – Tu at 9 pm and on W – Su at 7 and 9 pm at the Aquaplex, 711 Duval St.Info: 305-294-0555; aquakeywest.com.
Cabaret @ D’Vine Wine Gallery
Key West: This is an excellent hang if you want to kick back with a fine glass of wine and settle in for an intimate cabaret performance by some of Key West’s favorite performers, including classical guitarist Matteo Jampol and pianist Bobby Green. Takes place from 5 – 7 pm at The Gardens Hotel and Cottages, 26 Angela St. Info: 305-294-2661; gardenshotel.com.
Jazz at Tavern N’ Town
Key West: Some of Key West’s top talent, including “Island Chanteuse,” Carmen Rodriguez and Michael Thomas, perform nightly from 5 – 7 pm during Key West’s best Happy Hour. Takes place at Beachside Resort & Residences, 3841 N Roosevelt Blvd. Info: 305-296-8100; tavernntown.com.
Tuesday – Saturday
Christopher Peterson’s Birdcage Cabaret
Key West: Christopher Peterson is, without a doubt, one of North America’s foremost female impressionists — visually and vocally. Often compared to the legendary master of impersonations, Jim Bailey, Christopher’s lavish 90-minute show is one of the hottest tickets in town. Backed up by the outrageous Aquanettes Drag Queens, it’s one show you don’t want to miss. Takes place at 8 pm every Tu – Sa at the Birdcage Cabaret, 504 Angela St, in the Aquaplex. Info: 305-294-0555; aquakeywest.com.
Wednesday – Sunday
Comedy Magic Bar:
The Magic of Frank Everhart
Key West: Key West comedian and master magician, Frank Everhart, never ceases to amaze. Regaled as one of the country’s top comedians and magicians, Everhart’s “Chicago-style, close-up magic show” not only showcases his awe-inspiring magic, but it’s also absolutely hilarious. Showtime: 7 pm every W – Su at the notorious Schooner Wharf Bar, 202 William St in Key West’s Historic Seaport. Info: 305-292-9520; schoonerwharf.com.
Wednesday – Saturday
Cabaret in The Gardens
Key West: Key West’s Gardens Hotel is one of the most luxe boutique hotels on the island. Every W – Sa from 5 – 7 pm, you can enjoy outstanding live piano music in the Hotel’s intimate Cabaret. Full bar and stellar wines are the coup de gras. Find the Gardens Hotel at 526 Angela St. Info: 305-294-2661; gardenshotel.com.
Every Friday
The Fabulous Spectrelles Revue
Key West: Grab your dancing shoes and get ready to party! Key West’s longest-running show is an immersive, rollicking ride down memory lane. This high-energy revue has been rocking the house for over four decades and pays tribute to some of the world’s most renowned Motown and Doo-Wop groups from the ’50s and ’60s. Founder, Allison Mayer,aka “Baby Tracy Spectrelle,” and her chart-topping revue have played with some of Motown’s biggest stars, including Chuck Berry, the Coasters, the Drifters, and other notables. It’s a journey through music history that you don’t want to miss! Showtime: 7 – 8 pm at the Key West EmPOURium at Kaya Island Eats, 618 Duval St. Info & tickets: 305-395-0213; empouriumkeywest.com.
Every Sunday
Jazz in the Gardens
Key West: Enjoy terrific jazz amidst lush flora and fauna during this free hang that draws Key West’s top jazz cognoscenti. Full bar, champagne, and fabulous wines. This popular Sunday happening takes place from 5:30 – 8 pm at the Gardens Hotel, 526 Angela St. Info: 305-294-2661; gardenshotel.com.
SPECIAL EVENTS
May 15
25 Years of Close-Up Magic
Key West: Prepare to be amazed as the Comedy Magic Bar commemorates a quarter century of legendary magical entertainment! Renowned as one of the country’s top comedians and magicians, headliner Frank Everhart and friends dazzle and delight with lots of tricks and no sleeves to put them up! Hosted by local celebrity Bill Hoebee, this historical night also includes live music and dancing, as well as a late-night special appearance by global magic sensation, magician and illusionist, Nicholas Tweedy. Kicks off at 7 pm at Schooner Wharf Bar, 202 William St in the Historic Seaport. Info: 305-292-9520; schoonerwharf.com.
May 30
19th Annual Key West Follies
Key West: A precursor to Key West’s annual Pride Celebration, this campy variety show includes an array of unforgettable comedy, singing, dancing, and lots of belly busters. Hosted by Domini Paolillo and Claire Caplan, it’s an outrageous show that gets better and better every year! Full bar service. FYI: Always a “sell out,” so get your tickets early. Showtime: 7:30 pm at the Key West Theater, 512 Eaton St. Info & tickets: 305-985-0433; keywesttheater.com.
June 5
BERTHA: Grateful Drag
Key West: Cited as having the “best harmonies and vocals of any Grateful Dead tribute act,” this nationally celebrated, all-star collective reimagines The Dead’s music through bold drag performances, powerful vocals, and an electrifying stage presence. Doors open: 7 pm at the Key West Theater, 512 Eaton St. Info & tickets: 305-985-0433; keywesttheater.com.
July 10 – 11
42nd Annual Underwater Music Festival
Big Pine & The Lower Keys: The 42nd edition of this quirky underwater concert for divers, snorkelers, and the occasional mermaid is one of the summer’s biggest events. The annual shindig, which promotes reef preservation, kicks off on Friday from 6 – 8 pm with live music, lite bites, and beverages at Mote Marine, 24244 Overseas Hwy on Summerland Key. The submerged Songfest, which is also broadcast on US Radio 104.1 FM, takes place Saturday at Looe Key Reef in the Florida Keys National Marine Sanctuary, approximately 5 miles south of Big Pine Key. Transportation is available from the local dive shops. Info: 305- 872-2411; lowerkeyschamber.com.
July 15 – 25
The Clouds Over the Sunshine Inn
Key West: This sneak peek at Ben Harrison’s delicious new Romcom Musical begs the question: “Will corporate greed get its just deserts when it stands in the way of true love?” Produced by Art House, Fringe. Showtime: 7 pm at the Armory, 600White St. Info & reserved tickets: 305-295-7676; keystix.com.
August 1
One Night Stand
Key West: One of the summer’s most popular happenings, One Night Stand calls on creative thinkers to develop five brand-new theater pieces from start to finish in only 24 hours. With the clock ticking, dozens of people work together wickedly fast to make the project come to fruition. Showtimes: 7 and 9 pm in the Helmerich Theater at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
COMING SOON
September 3 – 7
Just A Few Friends Key West — Favorite Son Celebration
Key West: This 2nd annual celebration honors Key West’s favorite son, Jimmy Buffett, who passed away in 2024. Pre-Party events kick off early on W, Sept 2 with a special Jimmy Buffett Tribute Show at Comedy Key West and a Welcome Pre-Party at The Pier House’s famous Chart Room Bar. The festival officially kicks off on Th, Sept 3 with a jam-packed weekend lineup that includes foodie events, street, beach & pool parties, sailing adventures, bar strolls and more. On Su, Sep 6, you can enjoy the epic Second Line Walking Parade, which culminates with a huge party and concert on the waterfront. Come Monday, the weekend wraps up with even more activities, including the now famous Pencil Thin Mustache Contest, an Island Tiki Sunset & Music Cruise, and a fierce bayside concert with Caymen & The Mango Men on Sunset Pier. For more info, event badges and a full list of happenings, hit up justafewfriendskeywest.com.
