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
71 events found.
Events for April 23, 2026
Ongoing
Wednesday Filet Day at Mary Ellen’s
Mary Ellen's Wednesday Filet Day is a must-visit in Old Town Key West, where the lively atmosphere pairs perfectly with live music from talented local…
Free
DJ Todd at Red Garter Saloon Stage
DJ Todd is an innovative and electrifying DJ renowned for his eclectic mixes and high-energy performances. Known for captivating audiences with his unique soundscapes and…
Free
DJ Duke at Rick’s Bar Upstairs Stage
DJ Duke is a renowned music producer and DJ celebrated for his captivating mixes and electrifying performances. Known for blending genres seamlessly, he enthralls audiences…
Free
Crank Sinatra at Durty Harry’s Stage
Experience the electric energy of Krank Sinatra at Durty Harry's Stage in Key West. This multi-talented musician captivates audiences with his powerful vocals and masterful…
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 transforming the modern cover band scene, Alex Anthony delivers unforgettable…
Free
Karaoke at Bobby’s Monkey Bar
Enjoy a vibrant night of music at Bobby's Monkey Bar in Key West's Old Town. Experience the lively island atmosphere as entertainers bring the karaoke…
Kari Wolf at Irish Kevin’s Bar
Kari Wolf, an electrifying musician from Key West, enthralls audiences at Irish Kevin's Bar with her soulful melodies and captivating performances. Her unique style creates…
Free
Radio Hero at Sloppy Joe’s Bar
Radio Hero is an electrifying party rock band performing at Sloppy Joe's Bar, known for their high-energy and dynamic sound. Their explosive performances blend rock…
Free
Karaoke w/ Davis at Rick’s Bar Downstairs Stage
Join DJ Davis at Rick's Bar Downstairs Stage for an electrifying karaoke night. Known for his charismatic performances and diverse music selections, Davis brings infectious…
Free
Ambitious Morning Runners
Join the Ambitious Morning Runners event at White Street Pier in Key West, a picturesque location ideal for early risers. Enjoy breathtaking ocean views as…
Free
Yoga on the Beach – Ft Zachary Taylor
Experience tranquility with Yoga on the Beach at Fort Zachary Taylor State Park. Immerse yourself in a serene environment while practicing yoga with expert guidance.…
$20
Aqua yoga
Experience the soothing practice of Aqua Yoga at the Doubletree by Hilton Key Resort. Led by skilled instructors, this unique activity combines the benefits of…
Free
Alfonse at Two Friends Patio Restaurant
Experience the vibrant performances of Alfonse, a talented musician, at Two Friends Patio Restaurant. This Key West staple, nestled near Mallory Square, offers an inviting…
Free
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga at the stunning Key West Tropical Forest & Botanical Garden. Monica, an experienced yoga instructor, guides participants…
$20
Justin Angelo at Sloppy Joe’s Bar
At Sloppy Joe's Bar, Justin Angelo captivates audiences with his versatile music, reminiscent of icons like John Mayer and Jason Mraz. As a Certified Pro…
Free
Robert Douglas at Rams Head Southernmost
Experience the captivating performance of Robert Douglas at Rams Head Southernmost, an open-air venue known for its vibrant island atmosphere and live music. Enjoy Douglas's…
Free
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O’Maolain brings vibrant energy to Irish Kevin’s Bar, captivating audiences with his dynamic performances and interactive style. Known for his engaging presence, Mylo transforms…
Free
Trenton Chandler at Rick’s DownStairs Stage
Experience the soulful sounds of Trenton Chandler at Rick's DownStairs Stage. A Shallowater, Texas native, Chandler captivates audiences with his heartfelt country music, influenced by…
Free
Dan Harvey at Hog’s Breath Saloon
Dan Harvey brings his versatile musical talent to Hog's Breath Saloon, creating unforgettable moments in the heart of Key West. Whether performing solo, as a…
Free
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan energizes Sloppy Joe's Bar with his captivating performances, bringing dynamic live music to this iconic Key West venue. As a talented musician, he…
Free
Ross Brown at Schooner Wharf Bar
Ross Brown is an adventurous and versatile musician performing at Schooner Wharf Bar in Key West. Known as a Spiritual Gangster, he infuses creativity and…
Free
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Experience an entertaining tribute to Jimmy Buffett at Comedy Key West, led by acclaimed musician Caleb Hogan. This lively show captures Buffett's essence through vibrant…
$28
Shanty Hounds at Two Friends Patio Restaurant
Experience the lively and inventive acoustic duo Shanty Hounds at Two Friends Patio Restaurant in Key West. Featuring Dani Hoy and Key West Chris Rehm,…
Free
Truman Waterfront Farmers Market
The Truman Waterfront Farmers Market in Key West is a lively event held at Truman Waterfront Park, featuring local food and crafts. A key highlight…
Free
Just George at The Alamo Key West
Join Just George at The Alamo Key West for a captivating acoustic experience. Known for his heartfelt performances, Just George brings soulful melodies that embody…
Free
TRUMAN WATERFRONT FARMERS MARKET – CONCH REPUBLIC EDITION
Experience the vibrant TRUMAN WATERFRONT FARMERS MARKET – CONCH REPUBLIC EDITION at Key West's picturesque Truman Waterfront Park. While soaking in breathtaking ocean views, enjoy…
Free
Zack Lovering at Tiki House Key West
Zack Lovering, an accomplished local musician from the Florida Keys, brings his enchanting performances to Tiki House Key West. Known for his soulful melodies and…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin is the heart and soul of Irish Kevin’s Bar in Key West. This laid-back entertainer captivates audiences with his charm, humor, and musical…
Free
Jeff Harris at Rick’s Bar Downstairs
Experience a captivating evening with Jeff Harris at Rick's Bar Downstairs in Key West. Jeff, a multi-talented artist, seamlessly blends music and comedy, captivating audiences…
Free
Erica Sunshine Lee at Mac’s Place
Join Erica Sunshine Lee at Mac's Place in Key West for an unforgettable live music experience. This Nashville recording artist and passionate country singer from…
Free
44th Annual INDEPENDENCE DAY CEREMONY
The 44th Annual Independence Day Ceremony at Mallory Square celebrates our Tiny Island Nation's founding. Delight in vibrant street performances amidst stunning ocean sunsets, featuring…
Free
Ross Brown Duo at Hog’s Breath Saloon
Experience the captivating performance of Ross Brown Duo at the Hog's Breath Saloon in Key West. Celebrated for his versatility and adventurous spirit, Ross Brown…
Free
World Famous 801 Girls- 5pm Show
Experience the dazzling talent of the World Famous 801 Girls in their 5pm show at the 801 Bourbon Bar. Renowned for their captivating performances, these…
Micah Read at Rams Head Southernmost
Experience the captivating performance of Micah Read at Rams Head Southernmost. Known for his soulful vocals and dynamic guitar skills, Micah creates an unforgettable musical…
Free
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square, where the true stars are the street performers. Be captivated by jugglers and the renowned cat man…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the lively sounds of Caribe at El Meson de Pepes on Mallory Square in Key West. This vibrant Cuban restaurant, known for its rich…
Ericson Holt at Two Friends Patio Restaurant
Experience the captivating sounds of Ericson Holt at Two Friends Patio Restaurant in Key West. Known for his soulful performances, Ericson effortlessly blends blues and…
Free
LuffKid & Friends at Green Parrot Bar
Headlined by LuffKid & Friends, the event at the Green Parrot Bar promises a night of unforgettable live music. LuffKid, known for their electrifying performances…
Free
Preacher Pete Presents at Sloppy Joe’s Bar
Experience the captivating presence of Preacher Pete at Sloppy Joe's Bar in Key West. Known for his charismatic delivery and profound spiritual insights, Pete engages…
Free
PARADE PRE-PARTY
Join the PARADE PRE-PARTY at Mansion by the Sea’s Seaside Café, 1400 Duval St., featuring vibrant live music that sets the stage for an unforgettable…
Free
Bria Ansara at Berlin’s Cocktail Bar
At Berlin's Cocktail Bar, immerse yourself in the enchanting melodies of Bria Ansara. Her captivating jazz performance complements the bar's timeless charm, creating an unforgettable…
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
Dinner with the Dead – Rainbow Full of Sound Waynard in the Grand Piano at Viva Argentinian Steakhouse
Join the captivating Waynard Scheller at Viva Argentinian Steakhouse for an unforgettable evening. Known for his dynamic performances with Rainbow Full of Sound, Scheller's energetic…
Free
Barrett Thomas at The Alamo Key West
Barrett Thomas, a dynamic and talented musician based in Key West, is renowned for his innovative live performances. As a skilled looper, he artfully layers…
Free
Oren Polak at Irish Kevin’s Bar
Experience the dynamic performance of Oren Polak at Irish Kevin’s Bar, where his captivating talent and unique sound light up the stage. As a versatile…
Free
Terri, Larry and Friends Live Music at William Weech American Legion Post 168
Terri, Larry, and Friends Live Music is a dynamic musical ensemble celebrated for their electrifying performances. With a blend of diverse genres, they captivate audiences…
Free
Catch The Mania Trivia at Brady’s Pub
Join the excitement at Brady's Pub in Key West for Catch The Mania Trivia. Hosted by a dynamic and entertaining quizmaster, this lively event promises…
Free
Wicked Bingo at The Retro Room
Experience Wicked Bingo at The Retro Room, where the spotlight is on our dynamic entertainer who flawlessly blends humor and excitement, creating an unforgettable atmosphere.…
Free
Andy’s Cabana Open Mic No Mic Night
Andy's Cabana in Key West's Bahama Village transforms into a lively stage during the Open Mic No Mic Night, where talented entertainers captivate the audience…
Free
Joe The Show at Rick’s Bar Downstairs Stage
Joe The Show, also known as JTS, is a powerhouse performer captivating audiences with his vibrant energy and exceptional talent. Well-regarded for his dedication and…
Free
Nick Brownell at Schooner Wharf Bar
Nick Brownell, a talented musician from Key West, brings his captivating live performances to Schooner Wharf Bar. Known for his diverse setlist, Nick performs on…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the captivating Magic of Frank Everhart at Schooner Wharf Bar, where the legendary magician enchants audiences with his innovative tricks and spellbinding storytelling. Renowned…
Free
DJ Marty at Red Garter Saloon Stage
DJ Marty is a dynamic and innovative music curator renowned for his electrifying performances at the Red Garter Saloon Stage. His seamless mixing skills and…
Free
43rd Annual WORLD’S LOOOOONGEST PARADE
Join the 43rd Annual WORLD’S LOOOOONGEST PARADE on Duval Street, featuring captivating entertainers who bring the lively spirit of the Conch Republic to life. Amidst…
Free
Kristen McNamara at La Te Da
Kristen McNamara, performing at La Te Da in Key West, captivates audiences with her soulful singing and evocative songwriting. Her music, inspired by the Caribbean's…
Free
Zach Lovering at Halo Rooftop Lounge Bar at The Saint
Join vibrant local musician Zach Lovering at the Halo Rooftop Lounge Bar at The Saint Hotel in Key West. Known for his captivating performances and…
Free
Nick Mazza Miss Island Queen Fundraiser at Tiki House Key West
Join the Nick Mazza Miss Island Queen Fundraiser at Tiki House Key West for an unforgettable evening. Known for his dynamic performances, Nick Mazza promises…
Free
DJ Chaka at Rick’s Bar Upstairs Stage
Experience the electric energy of DJ Chaka at Rick's Bar Upstairs Stage. A dynamic entrepreneur and cancer survivor, DJ Chaka infuses every performance with passion…
Free
LuffKid & Friends at Green Parrot Bar
LuffKid and Friends take the stage at the legendary Green Parrot Bar in Key West, bringing their vibrant energy and captivating performances to this iconic…
Free
Tony V at Comedy Key West
Experience the comedic genius of Tony V at Comedy Key West. Crowned Funniest Person in Massachusetts, Tony has graced HBO, Comedy Central, and more. Known…
$35
Durtbags at Durty Harry’s Stage
Catch The Durtbags live at Durty Harry's Stage, where they deliver the ultimate party experience in Key West. As the town's biggest party/rock band, their…
Free
Randy Roberts at La Te Da
Randy Roberts captivates at La Te Da with extraordinary drag performances in Key West. Celebrated for live, impassioned vocals rather than lip-syncing, Randy has wowed…
$35
SCHOONER WHARF BAR PARADE AFTER-PARTY
Experience the lively Schooner Wharf Bar Parade After-Party, where the star attraction is captivated by phenomenal live music under the stars. Dance alongside CR VIPs,…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience an unforgettable night with the Alex Anthony Band at Hog's Breath Saloon in Key West. Renowned for reinventing the modern cover band experience, the…
Free
Karaoke with Foss at RockHouse Live
Join Foss for an unforgettable karaoke night at RockHouse Live, Key West. Known for his electrifying presence and talent, Foss elevates the evening with engaging…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant nightlife at Bobby's Monkey Bar in Old Town Key West, where the standout entertainer takes the stage for an unforgettable karaoke experience.…
Radio Hero at Sloppy Joe’s Bar
Experience the electrifying energy of Radio Hero at Sloppy Joe's Bar. Known for their explosive and edgy party rock, this dynamic band captivates audiences with…
Free
LuffKid & Friends at Green Parrot Bar
Experience the dynamic energy of LuffKid & Friends at the Green Parrot Bar in Key West. Known for their electrifying performances, LuffKid brings an unforgettable…
Free
Riptide Riot at Irish Kevin’s Bar
Riptide Riot is a dynamic power duo from Key West performing at Irish Kevin's Bar. Comprised of Jim Simonian on drums and vocals and Tim…
Free
Karaoke w/ Jason at Rick’s Bar Downstairs Stage
Join DJ Jason at Rick's Bar Downstairs Stage for an exhilarating night of karaoke. Known for his electrifying beats and seamless mixes, Jason effortlessly transforms…
Free