Key West is a place for everyone. The LGBTQ community goes beyond everyone accepts everyone. It is a melting pot of inclusivity. The entertainment allows you to live as who you want to be—not as who you hope to be. There’s a bit of everything for all people. Greats like Tennessee Williams and Ernest Hemingway made their homes here. The inclusiveness in entertainment matches the Monroe County doctrine: “One Human Family”.
Singers are more than just the tropical band or singer in the boardwalk bar on Duval. They have versatility and frequently also play instruments and write their own songs. This region is home to multiple events for showcasing singers and songwriters. You can see it from the high seas to the tiki bar. Just be ready to be blown away by the talent.
Earl Bud Lee, Alan Scherz, Dillon Dixon, and Marjory Lee perform regularly for a group called Gay Key West. These singers, along with Brendan and Peter Mayer hold a special time of “commotion on the ocean”. These relaxed guitar vocals, tropical acoustic, and some upbeat rock will encourage you truly to “Sail With the Songwriters”. Be sure to keep up with the news on all of their regularly scheduled shenanigans.
Michael McCloud and friends who plays blues and country form his band. He writes about common life. The Paul Cotton Band plays more of a rock nautical. It is oriented more toward heavy lyrics, depth and dynamics. They began in a garage in San Diego and are now in Key West. Malcolm and the Fiddle Trio also don the acoustics and make their stringed presence known. Their folk style blends well with the other artists for a variety of live guitar throw down. You can see them all at the Schooner Wharf Bar at Harborwalk on William Street in Key West.
Latinas, Broadway queens, classic divas, and BDSM bunnies are all just a few of the members of the drag community represented in Key West’s tapestry. Everyone assumes they are all just on Duval Street but you can find them all over the island and throughout the keys. They perform for Business Guild concerts and charity fundraisers. Yes, the night club and guesthouse performers abound, but this area’s drag community is multitalented as well as multicultural.
Check out Elle Taylor. This local icon is one of the most creative with costumes and movement. Her outfits will dazzle you and dance style enthrall every audience member. She is a staple at Aqua on Duval Street. Faith is also a Key West queen of fame. Having recently celebrated a milestone birthday, Aqua allows this diva to throw some parties regularly. These aren’t just any party. They are drag at its’ finest. There are six “Aquanettes” performing here and you don’t want to miss a single one.
Drag sisters Kelly Mandjaro Transformiste and Rebecca Show Transformiste love to strike a pose with their bar regulars and visitors alike. Leather, latex and sequins are their du jour clubwear. Rebecca is French and frequently does French numbers along with many tre chic looks. You can catch both sisters at 801 Bourbon Cabaret. Drinking diva Molly Mormen takes the stage regularly at Below Zero Lounge. She loves her Stoli and other cocktails to mix. Be sure not to miss this beautiful Key West energy.
Many of the bars throughout the Keys have smaller lounge or dance rooms attached. And then, some other venues have larger central rooms for your dancing pleasure. The tunes range from tropical to sexy house. No matter your taste, you can always find something just for you in these establishments. Mosey on up for some of the best spinning on the East Coast.
DJ Robbie Rivera pumps out the sexy house. His production group Juicy Music drops some amazing beats at Aqua’s Side Bar on the regular. DJ Mo spins regularly for the Bear community and has his own production company called “DJ Bo Music Productions”. He is a regular at Bourbon St. Pub, which is attached to the Orleans Bourbon guesthouse. Mashups, house, techno, classic hits and solid beats make his music desirable for all crowds.
One of Key West’s premiere female DJ’s is Blondie. Blondie spins club hits as well as modern dance electronica. Her style is clean and contemporary and forward focused. She was a featured DJ for the 2018 Key West Film Festival and takes the booth regularly at Mangoes Restaurant Duval Street. Vinicio Rotelli and DJ Cr3my bring their industrial playground style music to Club A for many major events. The tunes range from industrial chic to powerfully punching house. Ask a local on the street frequenting Fantasy Fest and they will tell you this is some of Key West’s finest spinning.
The Keys abound in humorous comedians stage crafting masterful sets. They partner with eye popping venues as well as kitschy corner bars to keep the laughter rolling. The diversity also applies here to the world of comedy. Key West is one humorous human family.
Jessimae Peluso headlines a venue known as Comedy Key West at Bottle Cap. Her emcee suave headlines the lineup. Hailing from Syracuse, she is a Key West snowbird regular. Alongside her is Stephanie Kaple, Tony Hughes, Steve Crane, Ian Lauritzen, Gwen Filosa and Kathy Gilmore. This group also has some of the best open mic nights in the islands. Comedy Key West troupe also offers a drunken spelling bee at Mary Ellen’s Bar Appelrouth Lane every Monday night.
Hailing from Seattle, Washington, Pony Charvet is a regular performer in the Key West theatre scene. He is also part of the cast of Comedy Key West troupe. He along with Joe Madaus, the founder of Comedy Key West, pack the Key West theatre every summer for a summer series of laughs. Don’t miss a trip to the Bottle Cap.
The city that gives the world a drag queen in a shoe every New Year’s Eve is no stranger also to cabaret and burlesque. You never know what you will find around every corner. Be read for every sultry and sassy moment. The surprises abound as you make way for the performers to razzle and dazzle.
Laurie Breakwell, Traci Reynolds, Gayla Morgan, and Amy Ray are the Cabaret gals. Headlining the same stage for the gents is Michael McCabe, Bruce Moore, and Bobby Nesbitt. Every night at the LaTeDa Crystal Room is a differing night of the Cabaret waters. Sail the musical seas as this troupe takes you on a journey in the Crystal Room on Sunday and Tuesday evenings. Randy Roberts does Bawdy, Blues and Broadway. This gorgeous queen appears as many legends from Cher to Reba. She also headlines La Te Da and performs with the Crazy Coqs Cabaret troupe.
Tatah DuJour, Cheeky Derriere, Nick Mazza, Pinky Starlight, Holy Peno, and Betty Pickle shake it like a polaroid in classic burlesque style. If you enjoy burlesque, don’t miss this group known as the Durty Birdie Burlesque troupe. They are at the Green Parrot bar regularly. Sunset Pier bar also plays host to Cheeky, Tito, Tatah, and Velvet during an annual pier New Years’ Eve party. French burlesque is also found on Duval. La Te Da transforms into a Je Taime Beaucoup frilly French Burlesque Cabaret starring the Burly-q Key West Burlesque group. Moana Amour appears with this group also in style and does cool themes like Wonderland Finito. This show was at Red Barn.
Enjoy the Best Entertainment in the Florida Keys
The entertainment for this region, as any other region, takes hours of preparation. However, the delivery in the Keys is top notch when it comes to entertainment. This community puts its’ heart and soul into its’ work. Don’t be fooled—not every single act is in Key West. One can find some adventures on Islamorada, Key Largo, and Big Pine as well. However, the pinnacle is no doubt Key West. It is also a pleasure to see all of the entertainers and venues reopening safely at this present time. They care about each other as well as their audience. This is truly an endearing chain of islands.
Click here to learn about more Florida Keys.
Written by Johnathan Soots
Hailing from North Carolina, Jonathan Soots relocated to Orlando in 2001. He began a seven year career with Universal Orlando. After completing high school, he attended college in Tennessee. He worked in the church world and then came out in 2010. Around this time, he completed a Masters in Teaching. Jonathan presently teaches for Tutor Doctor, Challenge Island and Qkids English Learning. Travel is his favorite activity, and he has worked briefly for an LGBT travel company. In addition to enjoying Atlantis gay cruises, he and his husband Stephen enjoy spending time with their silky terrier Dusty. They live in the South Pasadena area of St. Petersburg.
**Disclaimer: There is a good chance that this post contains affiliate or sponsor links. If you make a purchase through them, we may receive a small commission at no extra cost to you (for which we are extremely grateful).
Also, while we do our best to highlight LGBTQ-friendly destinations and businesses, info provided is based solely on personal experience and recommendations by community partners. We hope that nobody experiences discrimination or homophobia while visiting Florida, but we make no guarantees. Please inform us if you experience discrimination or homophobia while visiting any destination so we can make updates to our recommendations.