Wednesday Filet Day at Mary Ellen’s
Every Wednesday, Mary Ellen's in Old Town Key West hosts Filet Day, featuring an exciting lineup of entertainers to enhance your dining experience. Enjoy the…
Free
55 events found.
Events for April 30, 2026
Ongoing
Shelby Kemp Band at Hog’s Breath Saloon
The Shelby Kemp Band electrifies audiences at the Hog's Breath Saloon with their vibrant fusion of rock, blues, and soul. Frontman Shelby Kemp leads this…
Free
Karaoke at Bobby’s Monkey Bar
Karaoke at Bobby's Monkey Bar features a vibrant island atmosphere in Key West's Old Town. The highlight is the dynamic karaoke sessions led by charismatic…
Kari Wolf at Irish Kevin’s Bar
Experience the enchanting musical talents of Kari Wolf at Irish Kevin's Bar. A dynamic musician from Key West, Kari captivates audiences with her soulful melodies…
Free
The Audio Files at Sloppy Joe’s Bar
The Audio Files will captivate audiences at Sloppy Joe's Bar, combining storytelling, interviews, and meditative music into a rich auditory experience. Known for their dynamic…
Free
Ambitious Morning Runners
Join the Ambitious Morning Runners at White Street Pier in Key West, where you can start your day with invigorating runs and breathtaking oceanfront views.…
Free
Yoga on the Beach – Ft Zachary Taylor
Enjoy a rejuvenating Yoga on the Beach session at Fort Zachary Taylor in Key West. This historic location offers a unique blend of Civil War…
$20
Alfonse at Two Friends Patio Restaurant
Experience the vibrant sounds of musician Alfonse at Two Friends Patio Restaurant in Key West. Enjoy his captivating performances amidst a lively atmosphere, where fresh…
Free
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga at the breathtaking Key West Tropical Forest & Botanical Garden. Monica, renowned for her transformative yoga sessions,…
$20
Joe The Show at Sloppy Joe’s Bar
Joe The Show, affectionately known as JTS, electrifies audiences at Sloppy Joe's Bar with his dynamic energy and exceptional talent. As a dedicated musician and…
Free
Robert Douglas at Rams Head Southernmost
Robert Douglas captivates audiences at Rams Head Southernmost with his dynamic performances. Known for his versatility and engaging stage presence, Douglas delivers an unforgettable musical…
Free
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O'Maolain captivates audiences at Irish Kevin's Bar with his dynamic performances. Known for his engaging stage presence and musical talent, Mylo transforms the lively…
Free
Country Connected at Tiki House Key West
Experience the engaging performance of Country Connected at Tiki House Key West, where dynamic global collaboration meets live music. Immerse yourself in an evening of…
Free
Dan Harvey at Hog’s Breath Saloon
Dan Harvey captivates audiences at Hog's Breath Saloon with his versatile musical talent. Whether performing solo, as a duo, or with a full band, his…
Free
Southernmost Beach Resort Beach Bash
Experience the vibrant Southernmost Beach Resort Beach Bash, featuring dynamic performances by talented artists like Caleb Lathrop, Pistol Pearl, and Sam Blasko. Set against the…
Free
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan fills Sloppy Joe's Bar with infectious energy and dynamic performances, captivating the audience in Key West's iconic venue. Known for his engaging stage…
Free
Ross Brown at Schooner Wharf Bar
Ross Brown, a versatile musician from Key West, enchants audiences at Schooner Wharf Bar with his dynamic performances. Infusing his passion for kiteboarding, sailing, and…
Free
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Experience the captivating talents of Caleb Hogan as he embodies Jimmy Buffett in A Pirate Looks Back at Comedy Key West. This lunch theater tribute…
$28
Shanty Hounds at Two Friends Patio Restaurant
Join the Shanty Hounds at Two Friends Patio Restaurant for an unforgettable musical experience. This inventive acoustic duo, featuring Dani Hoy and Key West Chris…
Free
Truman Waterfront Farmers Market
Every week, the Truman Waterfront Farmers Market in Key West buzzes with excitement as visitors enjoy lively performances from talented entertainers. Set against the stunning…
Free
Just George at The Alamo Key West
Experience the soulful melodies of Just George at The Alamo Key West. A passionate musician based in Florida's paradise, he captivates audiences with heartfelt acoustic…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin, a beloved entertainer at Irish Kevin's Bar in Key West, captivates audiences with his charm and humor. Known for his genuine spirit, he…
Free
Smash Farm at Tiki House Key West
Experience Smash Farm at Tiki House Key West, where entertainment meets sustainability. Smash Farm offers dynamic agricultural experiences with interactive exhibits and hands-on activities. Engage…
Free
Elle Haley with Dallas at Hank’s Hair of the Dog Saloon
Experience the enchanting sounds of Elle Haley as she graces the stage at Hank's Hair of the Dog Saloon in Key West. Known for her…
Free
Mike Stone Duo at Hog’s Breath Saloon
Experience the electrifying energy of the Mike Stone Duo at Hog's Breath Saloon. Led by talented musician Mike Stone, this dynamic duo captivates audiences with…
Free
World Famous 801 Girls- 5pm Show
Experience the dazzling spectacle of the World Famous 801 Girls at their 5pm show. These renowned entertainers captivate audiences with their charisma and vibrant performances…
Micah Read at Rams Head Southernmost
Micah Read captivates audiences at Rams Head Southernmost with his dynamic musical talent. Known for his engaging performances, Micah's music blends seamlessly with the vibrant…
Free
Sunset Celebration at Mallory Square
Experience the lively Sunset Celebration at Mallory Square in Key West. As the sun dips below the horizon, be captivated by enchanting street performers like…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West, a dynamic entertainer, captivates audiences at El Meson de Pepe’s on Mallory Square. Known for their vibrant performances, Caribe infuses the…
Ericson Holt at Two Friends Patio Restaurant
Experience the captivating talents of Ericson Holt at Two Friends Patio Restaurant. With a soulful blend of music, this accomplished musician creates an unforgettable atmosphere…
Free
Doug South Band at Green Parrot Bar
The Doug South Band brings an electrifying performance to the Green Parrot Bar, captivating audiences with their dynamic sound and charismatic presence. Known for their…
Free
Preacher Pete Presents at Sloppy Joe’s Bar
Experience the captivating charisma of Preacher Pete at Sloppy Joe's Bar. Known for his powerful sermons and empathetic demeanor, Pete captivates audiences with his deep…
Free
Filming Sit with Kit Podcast Episodes
Join the captivating entertainer Mr. Kit Carson at Angelina's Pizzeria in Key West for the Filming Sit with Kit podcast episodes. Engage in vibrant discussions…
Free
Bria Ansara at Berlin’s Cocktail Bar
Experience the mesmerizing talent of Bria Ansara at Berlin's Cocktail Bar, where her captivating jazz performances enhance the venue's nostalgic ambiance. Nestled within the historic…
Free
Dinner with the Dead – Rainbow Full of Sound Waynard in the Grand Piano at Viva Argentinian Steakhouse
Experience the captivating performance of Waynard Scheller at Viva Argentinian Steakhouse. Known for his dynamic keyboard and vocal talents, Scheller brings his energetic stage presence…
Free
Barrett Thomas at The Alamo Key West
Barrett Thomas is a dynamic musician and talented looper based in Key West, FL. Known for his innovative performances, he skillfully layers sounds to create…
Free
Songwriter Sail on the Schooner Hindu
Experience the enchanting talents of Beth Hataway and Johnny Veres from Electric Blue Yonder on the Schooner Hindu. Renowned for their Space Folk sound, the…
Free
Jay Bangles at Tiki House Key West
Experience the vibrant performances of Jay Bangles at Tiki House Key West. As co-owner and talented musician, Jay infuses his unique charm into the lively…
Free
Oren Polak at Irish Kevin’s Bar
Oren Polak takes the stage at Irish Kevin's Bar, enchanting audiences with his dynamic performances and unique musical flair. As a versatile musician and band…
Free
Terri, Larry and Friends Live Music at William Weech American Legion Post 168
Terri, Larry, and Friends Live Music is a dynamic ensemble celebrated for their electrifying performances that captivate audiences with infectious rhythms and soulful melodies. Known…
Free
Catch The Mania Trivia at Brady’s Pub
Immerse yourself in a thrilling evening hosted by the captivating entertainer at Brady's Pub's Catch The Mania Trivia night. Set in the vibrant atmosphere of…
Free
Wicked Bingo at The Retro Room
Experience an unforgettable evening with Wicked Bingo at The Retro Room in Old Town Key West. The lively entertainer will keep you engaged and entertained…
Free
Andy’s Cabana Open Mic No Mic Night
Experience an unforgettable evening at Andy's Cabana Open Mic No Mic Night, where talented local entertainers shine without amplification. Set in the vibrant ambiance of…
Free
Nick Brownell at Schooner Wharf Bar
Nick Brownell is a talented musician known for his captivating live performances at Key West's Schooner Wharf Bar. With a diverse set list, he entertains…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the mesmerizing Magic of Frank Everhart at Schooner Wharf Bar. Renowned for his innovative tricks and captivating storytelling, Everhart is a legendary magician who…
Free
Zach Lovering at Halo Rooftop Lounge Bar at The Saint
Zach Lovering, a dynamic local musician from the Florida Keys, captivates audiences at Halo Rooftop Lounge Bar with his soulful melodies and island-infused tunes. His…
Free
Doug South Band at Green Parrot Bar
Experience the Doug South Band at Green Parrot Bar in Key West, an iconic dive bar known for its vibrant live music scene. Doug South…
Free
Randy Roberts at La Te Da
Randy Roberts shines at La Te Da in Key West, delivering captivating cabaret performances with his electrifying, live vocals. Celebrated for over three decades, his…
$35
Shelby Kemp Band at Hog’s Breath Saloon
Experience the electrifying Shelby Kemp Band at Hog's Breath Saloon, known for their vibrant fusion of rock, blues, and soul. Frontman Shelby Kemp leads with…
Free
Karaoke with Foss at RockHouse Live
Join Foss for an unforgettable karaoke night at RockHouse Live Key West, where his charisma and engaging presence light up the stage. Experience a lively…
Free
Karaoke at Bobby’s Monkey Bar
Experience the vibrant energy of Karaoke at Bobby's Monkey Bar, where the star is the charismatic karaoke host who engages the lively crowd. Located in…
Nick Walker & The Rum Runners at Tiki House Key West
Nick Walker, a renowned UK street artist and muralist, brings his vibrant energy to Tiki House Key West. Known for his captivating contemporary art, Walker…
Free
The Audio Files at Sloppy Joe’s Bar
Experience an unforgettable evening with The Audio Files at Sloppy Joe's Bar, Key West. This dynamic platform delivers an immersive auditory journey, seamlessly blending captivating…
Free
Doug South Band at Green Parrot Bar
Doug South Band is set to energize the iconic Green Parrot Bar in Key West. Known for their dynamic performances and engaging musical prowess, Doug…
Free
Riptide Riot at Irish Kevin’s Bar
Experience the electrifying performance of Riptide Riot, a dynamic power duo captivating audiences at Irish Kevin's Bar in Key West. With Jim Simonian on drums…
Free