Wednesday Filet Day at Mary Ellen’s
Enjoy a vibrant evening at Mary Ellen's in Old Town Key West with Wednesday Filet Day. While savoring gourmet grilled cheese and craft beers, let…
Free
58 events found.
Events for April 9, 2026
Ongoing
DJ Todd at Red Garter Saloon Stage
Experience the electric energy of DJ Todd at the Red Garter Saloon Stage. Known for his eclectic mixes and captivating performances, DJ Todd masterfully blends…
Free
DJ Duke at Rick’s Bar Upstairs Stage
DJ Duke, a dynamic and innovative music producer, brings his mesmerizing mixes to Rick's Bar Upstairs Stage. Known for electrifying performances and a keen ear…
Free
Crank Sinatra at Durty Harry’s Stage
Experience the vibrant energy of Krank Sinatra at Durty Harry's Stage in Key West. As a versatile musician and engaging performer, he captivates audiences with…
Free
Matthew Curry Band at Hog’s Breath Saloon
Experience the electrifying Matthew Curry Band at Hog's Breath Saloon in Key West. Fronted by virtuoso guitarist and singer Matthew Curry, this blues-rock ensemble captivates…
Free
Karaoke at Bobby’s Monkey Bar
Join the lively atmosphere at Bobby's Monkey Bar in Key West's Old Town, where the spotlight shines on vibrant karaoke entertainers. Every night, talented performers…
Crownz at Sloppy Joe’s Bar
Crownz, the electrifying pop rock band from Tampa, FL, lights up Sloppy Joe's Bar with their dynamic sound and energetic performances. Known for blending catchy…
Free
Tim Bradach at Irish Kevin’s Bar
Tim Bradach captivates audiences at Irish Kevin's Bar with his dynamic musical performances. As a talented musician, he brings energy and excitement to the lively…
Free
Karaoke w/ Davis at Rick’s Bar Downstairs Stage
Join DJ Davis for an electrifying karaoke night at Rick's Bar Downstairs Stage. Known for his dynamic style and ability to captivate any audience, Davis…
Free
Ambitious Morning Runners
Join the Ambitious Morning Runners at White Street Pier in Key West, a vibrant gathering where stunning oceanfront views take center stage. As dawn breaks,…
Free
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for a daily party boat fishing experience at A & B Marina in Key West's historic seaport. Enjoy live entertainment amidst the…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Join us for Yoga on the Beach at Fort Zachary Taylor in Key West, where serene natural beauty meets history. Breathe in the salt-kissed air…
$20
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga at the stunning Key West Tropical Forest & Botanical Garden. As an experienced yoga instructor, Monica guides…
$20
Justin Angelo at Sloppy Joe’s Bar
Justin Angelo captivates the audience at Sloppy Joe's Bar with his versatile musicianship and evocative songwriting style, reminiscent of icons like John Mayer and Jason…
Free
Robert Douglas at Rams Head Southernmost
Robert Douglas captivates audiences at Rams Head Southernmost with his exceptional musical talent. Known for his engaging performances and dynamic presence, Robert brings an unforgettable…
Free
Mylo O’Maolain at Irish Kevin’s Bar
At Irish Kevin's Bar, Mylo O’Maolain captivates audiences with his dynamic performances and infectious energy. Known for his lively Irish tunes and charismatic stage presence,…
Free
Trenton Chandler at Rick’s DownStairs Stage
Trenton Chandler, a talented country musician from Shallowater, Texas, captivates audiences at Rick's DownStairs Stage with his heartfelt compositions. Drawing inspiration from West Texas legends…
Free
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant Key West Legal Rum Distillery with daily free tours and tastings. Although there’s no specific entertainer mentioned, the lively setting itself offers…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West Legal Rum Distillery with a minimum group of four. The entertainer, a spirited mixologist, will guide you through…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise for a unique maritime experience in Key West. While the tour offers breathtaking views of vibrant marine life through…
$69.95
Dan Harvey at Hog’s Breath Saloon
Experience the captivating talents of Dan Harvey at Hog's Breath Saloon in Key West. As a versatile musician, Dan Harvey delivers an unforgettable live music…
Free
Tim Hollohan at Sloppy Joe’s Bar
Experience the captivating performance of musician Tim Hollohan at Sloppy Joe's Bar, a historic venue in Key West. Known for his engaging presence and musical…
Free
Ross Brown at Schooner Wharf Bar
Ross Brown, a dynamic musician from Key West, captivates audiences with his unique blend of creativity and adventure at the Schooner Wharf Bar. Known as…
Free
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Experience Caleb Hogan's captivating performance in A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West. As a talented musician, actor, and Buffett…
$28
Tony Baltimore at Hank’s Hair of the Dog Saloon
Experience the captivating sounds of Tony Baltimore at Hank's Hair of the Dog Saloon. A multi-talented singer-songwriter and instrumentalist, Baltimore delivers genre-bending alternative roots-rock inspired…
Free
Truman Waterfront Farmers Market
Enjoy vibrant performances at the Truman Waterfront Farmers Market held at Truman Waterfront Park in Key West. The amphitheater hosts a variety of entertainers who…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the vibrant marine life of Key West aboard the Glass Bottom Boat Cruise, featuring captivating performances by talented local entertainers. This unique excursion combines…
$69.95
Jefff Clark at Tiki House Key West
Experience the captivating sounds of Jefff Clark at Tiki House Key West. A budding music artist, Jefff showcases his evolving talent through engaging visuals and…
Free
Just George at The Alamo Key West
Experience the captivating performances of Just George at The Alamo Key West. This talented musician brings soulful acoustic melodies to life, embodying the vibrant spirit…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin, the beloved entertainer at Irish Kevin's Bar in Key West, is renowned for his infectious charm and humor. A charismatic performer, Kevin captivates…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience the vibrant Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise at Sunset Watersports in Key West's Historic Seaport. Dive into an adventure with…
$79.95
Jeff Harris at Rick’s Bar Downstairs
Experience the captivating talents of Jeff Harris at Rick's Bar Downstairs in Key West. As a singer, songwriter, comedian, and author, Jeff delivers engaging performances…
Free
Collette Campbell at Mac’s Place
Collette Campbell, a talented singer-songwriter based in Key West, enchants audiences with her captivating storytelling and original music. With roots in Long Island and a…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West, where the ocean comes alive beneath your feet. Marvel at the vibrant marine life through…
$69.95
Adam Lufkin Duo at Hog’s Breath Saloon
Experience the unique sound of the Adam Lufkin Duo at Hog's Breath Saloon. Known as LuFFKiD, Adam Lufkin masterfully blends reggae, hip-hop, and rock, creating…
Free
World Famous 801 Girls- 5pm Show
Experience the dazzling charisma of the World Famous 801 Girls in their 5pm show. These talented drag performers captivate audiences with their vibrant energy and…
Elle Haley at Hank’s Hair of the Dog Saloon
Elle Haley enchants audiences with her soulful music at Hank's Hair of the Dog Saloon in Key West. Known for her captivating performances, Elle creates…
Free
Micah Read at Rams Head Southernmost
Micah Read brings his captivating musical talent to Rams Head Southernmost, offering an unforgettable live performance. In the heart of historic Bahama Village, guests can…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant sounds of Caribe of Key West at El Meson de Pepe's on Mallory Square. This family-owned Cuban restaurant is not only known…
Sunset Celebration at Mallory Square
Experience the Sunset Celebration at Mallory Square, where the vibrant atmosphere comes alive with captivating street performers. Among the highlights is the renowned cat man,…
Free
Bearly Dead at Green Parrot Bar
Experience the electrifying performance of Bearly Dead at the iconic Green Parrot Bar in Key West. Known for their dynamic renditions of Grateful Dead classics,…
Free
Preacher Pete Presents at Sloppy Joe’s Bar
Experience the captivating presence of Preacher Pete at Sloppy Joe's Bar, where this charismatic spiritual leader transforms a historic venue into a hub of faith…
Free
Bria Ansara at Berlin’s Cocktail Bar
Experience the enchanting performance of Bria Ansara at Berlin's Cocktail Bar, where her captivating jazz vocals resonate through the historic venue. As you relax in…
Free
Dinner with the Dead – Rainbow Full of Sound Waynard in the Grand Piano at Viva Argentinian Steakhouse
Join Dinner with the Dead at Viva Argentinian Steakhouse and experience the remarkable talents of Waynard Scheller. As a dynamic keyboardist and vocalist with Rainbow…
Free
Filming Sit with Kit Podcast Episodes
Join Kit for the filming of Sit with Kit Podcast Episodes at Angelina's Pizzeria in Key West. Known for lively and engaging conversations, Kit brings…
Free
Barrett Thomas at The Alamo Key West
Experience the dynamic performances of Barrett Thomas at The Alamo Key West. This talented musician and skilled looper captivates audiences with his innovative sound layering,…
Free
Oren Polak at Irish Kevin’s Bar
Oren Polak, a dynamic musician known for his captivating performances and distinctive sound, brings his energetic presence to Irish Kevin's Bar. As a versatile artist…
Free
Catch The Mania Trivia at Brady’s Pub
Join the electrifying Catch The Mania Trivia at Brady's Pub, where the spotlight shines on a captivating entertainer who keeps the night lively and engaging.…
Free
Wicked Bingo at The Retro Room
Join the vibrant atmosphere at The Retro Room for Wicked Bingo, led by a charismatic entertainer who brings energy and excitement to every round. Amidst…
Free
Andy’s Cabana Open Mic No Mic Night
Experience the electrifying talent of local performers at Andy's Cabana Open Mic No Mic Night in Key West's vibrant Bahama Village. With a lively atmosphere…
Free
Joe The Show at Rick’s Bar Downstairs Stage
Experience the captivating energy of Joe The Show at Rick's Bar Downstairs Stage. Known as JTS, this renowned musician performs daily in Key West, enchanting…
Free
Nick Brownell at Schooner Wharf Bar
Nick Brownell is a talented Key West musician renowned for his captivating live performances. He brings a diverse musical set to the Schooner Wharf Bar,…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting artistry of Frank Everhart at Schooner Wharf Bar. Renowned for his innovative tricks and captivating storytelling, Everhart mesmerizes audiences with a blend…
Free
DJ Marty at Red Garter Saloon Stage
DJ Marty, a dynamic and innovative music curator, thrills audiences at the Red Garter Saloon Stage with his electrifying performances and seamless mixing skills. Known…
Free
Kristen McNamara at La Te Da
Kristen McNamara is a gifted artist performing at La Te Da in Key West, captivating audiences with her soulful voice and evocative songwriting. Known for…
Free
Zach Lovering at Halo Rooftop Lounge Bar at The Saint
Zach Lovering, a vibrant musician from the Florida Keys, enchants audiences at Halo Rooftop Lounge Bar, The Saint Hotel, with his soulful melodies and island…
Free
Tony Baltimore at Tiki House Key West
Tony Baltimore, a dynamic singer/songwriter, brings his genre-bending alternative roots-rock to Tiki House Key West. With a strong work ethic instilled by his Italian immigrant…
Free
DJ Chaka at Rick’s Bar Upstairs Stage
DJ Chaka electrifies Rick's Bar Upstairs Stage with his unstoppable energy and passion for life. A resilient cancer survivor and vibrant entrepreneur from Key West,…
Free