WOOF Week 2026!
Experience the excitement of WOOF Week 2026 in Key West, featuring sizzling daytime and nighttime parties. The highlight of the event is electrifying performances by…
Free
65 events found.
Events for April 25, 2026
Ongoing
DJ Marty at Red Garter Saloon Stage
DJ Marty, a vibrant and innovative music curator, transforms the Red Garter Saloon Stage at Rick's Entertainment Complex into an electrifying experience with his seamless…
Free
DJ Duke at Rick’s Bar Upstairs Stage
DJ Duke is a dynamic music producer celebrated for his mesmerizing mixes and electrifying performances. Known for blending genres with a keen ear and vibrant…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience the electrifying performance of the Alex Anthony Band at Hog's Breath Saloon. Known for reinventing the modern cover band scene, Alex Anthony captivates audiences…
Free
Karaoke at Bobby’s Monkey Bar
Experience lively karaoke nights at Bobby's Monkey Bar in Key West's Old Town. Although specific entertainer details are not available, the vibrant island atmosphere and…
Mike Stack & DLew at Tiki House Key West
Mike Stack and DLew form a dynamic duo known for their innovative synergy at Tiki House Key West. Mike’s strategic insight combines seamlessly with DLew’s…
Free
Radio Hero at Sloppy Joe’s Bar
Experience the electrifying energy of Radio Hero at Sloppy Joe's Bar, a legendary Key West venue. Renowned for their dynamic sound and bold stage presence,…
Free
Riptide Riot at Irish Kevin’s Bar
Riptide Riot, a dynamic power duo from Key West, captivates audiences at Irish Kevin's Bar with their electrifying, all-request rock show. Featuring Jim Simonian on…
Free
Alfonse at Two Friends Patio Restaurant
Experience the captivating sounds of Alfonse at Two Friends Patio Restaurant, a beloved Key West venue. Enjoy his mesmerizing performances as Alfonse fills the open-air…
Free
Yoga on the Beach – Ft Zachary Taylor
Experience tranquility with Yoga on the Beach at Fort Zachary Taylor in Key West. While the park's stunning seascapes and rich Civil War history set…
$20
Prime of Life Yoga with Monica Haskell
Experience rejuvenation with Monica Haskell at Prime of Life Yoga, set amidst the enchanting Key West Tropical Forest & Botanical Garden. Monica, a seasoned yoga…
$20
Izzy Zaidman at Sloppy Joe’s Bar
Izzy Zaidman captivates audiences at Sloppy Joe's Bar with his dynamic guitar skills and engaging stage presence. A talented musician, composer, and singer-songwriter, Zaidman brings…
Free
OCEAN FEST – A COMMUNITY CELEBRATION
Join the vibrant Ocean Fest at Truman Waterfront Park for a lively community celebration. Enjoy captivating live music performances that set the perfect backdrop for…
Free
OCEAN & MANGROVE WEEKLY CLEANUP WITH THE CONCH REPUBIC MARINE ARMY
Join the Conch Republic Marine Army for the Ocean & Mangrove Weekly Cleanup, an engaging event dedicated to preserving Florida Keys' natural ecosystems. Departing from…
Free
Independent Bookstore Day
Celebrate Independent Bookstore Day at Books & Books on Saturday, April 25. This nationwide event highlights the charm of indie bookstores and honors book lovers…
Free
Jeff Harris at Irish Kevin’s Bar
Experience the captivating talent of Jeff Harris at Irish Kevin's Bar. A multi-talented American singer, songwriter, comedian, and author, Jeff skillfully blends music and humor,…
Free
5th Annual Cuban Sandwich Throwdown at Green Parrot Bar
Celebrate the 5th Annual Cuban Sandwich Throwdown at the Green Parrot Bar, an iconic dive bar in Key West renowned for its lively atmosphere. Experience…
Free
Joel Nelson at Two Friends Patio Restaurant
Experience the captivating performance of musician Joel Nelson at Two Friends Patio Restaurant, a renowned Key West venue. Nelson enchants guests with his melodic tunes…
Free
Cliff Cody at Hog’s Breath Saloon
Experience the soulful sounds of Cliff Cody at Hog's Breath Saloon. This Texas-born, Key West-based indie country singer captivates audiences with his powerful voice and…
Free
Zack Seemiller at Rick’s Bar Downstairs Stage
Experience the captivating performance of Zack Seemiller at Rick's Bar Downstairs Stage. Zack is a dynamic musician and songwriter celebrated for his engaging live shows.…
Free
Brian Roberts at Sloppy Joe’s Bar
Experience the captivating live performances of Brian Roberts at Sloppy Joe's Bar, where his talent as a singer and songwriter shines in the historic ambiance…
Free
Nick Brownell at Schooner Wharf Bar
Nick Brownell is a talented musician based in Key West renowned for his captivating live performances. At Schooner Wharf Bar, his diverse music sets enhance…
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
Joe The Show at Tiki House Key West
Experience the vibrant sounds of Joe The Show at Tiki House Key West. Known for his dynamic performances and tireless dedication, JTS captivates audiences with…
Free
43rd Annual Julie Hansen Memorial Bed Races on Duval
Experience the 43rd Annual Julie Hansen Memorial Bed Races on Duval and enjoy the vibrant entertainment provided by the World Famous 801 Girls. Known for…
Free
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary performer at Irish Kevin's Bar in Key West. Famed for his captivating shows, he delivers vibrant performances that seamlessly blend…
Free
Zac Kellum at Mac’s Place
Zac Kellum brings his dynamic musical talents to Mac's Place, a lively waterfront sports bar in Key West. Enjoy his captivating performances against the backdrop…
Free
Chris at Two Friends Patio Restaurant
Experience the vibrant island atmosphere as Chris entertains at Two Friends Patio Restaurant. This Key West classic, established in 1967, is renowned for its open-air…
Free
Bradd Shadduck at Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Bradd Shadduck at Rick's Bar Downstairs Stage, where his electrifying presence and musical prowess create an unforgettable night. Known…
Free
Jack Wolf at Tiki House Key West
Experience the soulful sounds of Jack Wolf at Tiki House Key West. A talented singer-songwriter, Jack captivates audiences with his heartfelt performances. Based in Key…
Free
Ross Brown Duo at Hog’s Breath Saloon
Experience the Ross Brown Duo at Hog's Breath Saloon and be captivated by Ross Brown's versatile musicianship. Based in Key West, Ross infuses his performances…
Free
World Famous 801 Girls- 5pm Show
Experience the dazzling performances of the World Famous 801 Girls at their 5pm show, held at the vibrant 801 Bourbon Bar in Key West. Known…
Charlie Miller at Rams Head Southernmost
Charlie Miller, an energetic musician and adventurous sailor, enchants audiences at Rams Head Southernmost. Embracing the spirit of a modern-day pirate and gypsy, Charlie's performances…
Free
Happy Dog at The Alamo Key West
Experience the captivating energy of Happy Dog Band at The Alamo Key West. This improvisational jam band channels the essence of the psychedelic era, inviting…
Free
Reelin for the Cause
Join us for the 6th Annual Reelin for the Cause Kids Fishing Tournament at the picturesque Ed Knight Pier in Key West on April 25,…
Free
Sunset Celebration at Mallory Square
Experience the Sunset Celebration at Mallory Square, where performers captivate with breathtaking acts. From daring jugglers to the enchanting antics of the famous cat man,…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant rhythms of Caribe of Key West at El Meson de Pepes on Mallory Square. This talented entertainer brings the lively spirit of…
Tim Palmieri & Friends at Green Parrot Bar
Join Tim Palmieri & Friends at the Green Parrot Bar, where their electrifying performances light up this iconic Key West dive bar. Known for his…
Free
Victoria Leigh at Sloppy Joe’s Bar
Victoria Leigh lights up Sloppy Joe's Bar with her captivating live performances. As a vibrant musician from the Florida Keys, she enchants audiences with feel-good…
Free
April’s Community Swim
Experience an enchanting evening at April's Community Swim with mesmerizing live music by Mermaid Dorian. Join us at the Shores Pool on April 25th at…
Free
Joe The Show at Durty Harry’s Stage
Joe The Show, a vibrant musician known for his relentless work ethic, lights up Durty Harry's Stage in Key West. Performing daily, he captivates with…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin is a charismatic and fun-loving entertainer known for his humor and charm at Irish Kevin's Bar in Key West’s Old Town. His captivating…
Free
42nd Annual Schooner Wharf Pirate Ball & Costume Competition
Experience the dynamic energy of the 42nd Annual Schooner Wharf Pirate Ball & Costume Competition, highlighted by captivating live music that brings a lively, island…
Free
42nd Annual Schooner Wharf Wreckers Cup Race Captains Meeting
The 42nd Annual Schooner Wharf Wreckers Cup Race Captains Meeting at the Schooner Wharf Bar promises an unforgettable evening. Set in a vibrant open-air venue…
Free
DJ Of Course Dave at The Retro Room
Join DJ Of Course Dave at The Retro Room for an unforgettable night of nostalgia. Known for his electrifying mixes and dynamic presence, DJ Of…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar. A legendary magician, Everhart captivates audiences with innovative tricks and mesmerizing storytelling. His performances…
Free
Scallywags Band at Schooner Wharf Bar
Experience the infectious energy of Scallywags Band at Schooner Wharf Bar. Known for their dynamic performances, the band delivers an exhilarating mix of tunes that…
Free
DJ Marty at Red Garter Saloon Stage
Experience the electrifying energy of DJ Marty at the Red Garter Saloon Stage. Known for his seamless mixing skills and dynamic performances, DJ Marty captivates…
Free
Karaoke at Two Friends Patio
Experience lively karaoke at Two Friends Patio, a beloved Key West destination. The highlight of the event is the charismatic entertainer who engages and energizes…
Free
Ronnie & Gregory at La Te Da
Experience the captivating performances of Ronnie and Gregory at La Te Da in Key West. This dynamic duo lights up the stage with their vibrant…
Free
Thomas Barrett at Halo Rooftop Lounge Bar at The Saint
Experience the captivating performance of Thomas Barrett at Halo Rooftop Lounge Bar. Known for his dynamic stage presence and musical prowess, Barrett creates an unforgettable…
Free
Michael Corleto at Rick’s Bar Downstairs Stage
Experience the captivating performances of Michael Corleto, a talented singer-songwriter and multi-instrumentalist from Maine, at Rick's Bar Downstairs Stage. With heartfelt lyrics and rich melodies,…
Free
DJ Chaka at Rick’s Bar Upstairs Stage
DJ Chaka, the dynamic Key West entrepreneur and cancer survivor, electrifies Rick's Bar Upstairs Stage with his infectious energy and passion for life. Known as…
Free
Tony V at Comedy Key West
Tony V, the renowned comedian, celebrated as the Funniest Person in Massachusetts, brings his wit and charm to Comedy Key West. Known for his unique…
$35
Neil Young Tribute at The Alamo Key West
Experience an electrifying Neil Young Tribute at The Alamo Key West, where dynamic live performances capture the essence of Neil Young's legendary music. Set in…
Free
Tim Palmieri & Friends at Green Parrot Bar
Tim Palmieri & Friends bring their dynamic and captivating musical talent to the Green Parrot Bar, an iconic venue in Key West. Known for his…
Free
Randy Roberts at La Te Da
Immerse yourself in the spellbinding world of Randy Roberts at La Te Da, where his extraordinary live performances set a new standard for drag entertainment.…
$35
Alex Anthony Band at Hog’s Breath Saloon
Experience the captivating performance of the Alex Anthony Band at Hog's Breath Saloon, where they redefine the modern cover band with seamless talent and an…
Free
The Tiki Bombs at Tiki House Key West
The Tiki Bombs, a dynamic band celebrated for their energetic performances, bring a tropical flair to Tiki House Key West. Blending traditional island melodies with…
Free
Durtbags at Durty Harry’s Stage
Experience the electrifying atmosphere of Key West with The Durtbags, the premier party rock band, at Durty Harry's Stage. Performing live from Thursday to Sunday,…
Free
Karaoke at Bobby’s Monkey Bar
Experience an unforgettable night of karaoke at Bobby's Monkey Bar, where the star of the show is the charismatic karaoke host. With their vibrant energy…
The Audio Files at Sloppy Joe’s Bar
Experience an unforgettable evening with The Audio Files at Sloppy Joe's Bar. Known for crafting rich, immersive auditory journeys, The Audio Files blend storytelling, meditative…
Free
Jack and Jim Show at Irish Kevin’s Bar
Experience the electrifying Jack and Jim Show at Irish Kevin's Bar in Key West. Renowned for dynamic performances, Jack and Jim captivate audiences with their…
Free
Tim Palmieri & Friends at Green Parrot Bar
Tim Palmieri, renowned for his musical prowess, takes center stage at the Green Parrot Bar with his band. Known for captivating performances, Tim blends diverse…
Free
Karaoke w/ Jason at Rick’s Bar Downstairs Stage
Experience an unforgettable night with DJ Jason at Rick's Bar Downstairs Stage. Known for his electrifying beats and seamless mixes, Jason transforms karaoke into a…
Free