Martini Monday at Virgilios
Experience Martini Monday at Virgilio’s in Old Town Key West, where you can savor exquisite martinis and enjoy live performances every evening. This stylish lounge…
Free
63 events found.
Events for April 14, 2026
Ongoing
DJ Marty at Red Garter Saloon Stage
DJ Marty, an innovative music curator, transforms the Red Garter Saloon Stage into an electrifying nightlife experience. Known for his seamless mixing skills and vibrant…
Free
DJ Duke at Rick’s Bar Upstairs Stage
DJ Duke delivers an electrifying performance at Rick's Bar Upstairs Stage. Known for his dynamic music production and mesmerizing mixes, his vibrant stage presence captivates…
Free
HYPER DRIVE at Durty Harry’s Stage
Experience the electrifying talent of Hyper Drive at Durty Harry's Stage, where his dynamic performances as a vocalist, guitarist, songwriter, and producer take center stage.…
Free
Homegrown at Hog’s Breath Saloon
Experience the vibrant sounds of Homegrown at Hog's Breath Saloon, a dynamic country band from Key West, Florida. With heartfelt lyrics and captivating melodies, they…
Free
Karaoke at Bobby’s Monkey Bar
Join the charismatic and talented performer at Bobby's Monkey Bar for an unforgettable night of karaoke in Key West's Old Town. The lively island atmosphere…
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O’Maolain delivers electrifying performances at Irish Kevin’s Bar, engaging audiences with his dynamic stage presence and captivating music. Known for creating an interactive and…
Free
Turning The Tide at Sloppy Joe’s Bar
Turning The Tide takes center stage at Sloppy Joe's Bar, weaving a compelling narrative about resilience and determination. Against a lively backdrop, this enthralling performance…
Free
Ambitious Morning Runners
Ambitious Morning Runners gather at the serene White Street Pier in Key West, a perfect backdrop for this invigorating event. While the pier offers breathtaking…
Free
Rising Star Series: Using AI to Improve Business Efficiency and Effectiveness
Join the Rising Star Series, hosted by the Greater Key West Chamber of Commerce at the elegant Casa Marina Resort. This interactive seminar focuses on…
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
Experience tranquility with Yoga on the Beach at Fort Zachary Taylor State Park in Key West. Immerse yourself in a unique session led by a…
$20
Jonthan Williams at Two Friends Patio Restaurant
Jonathan Williams captivates audiences at Two Friends Patio Restaurant with his dynamic live performances. Set against the backdrop of Key West's vibrant Duval Street, he…
Free
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga, a rejuvenating experience held at the unique Key West Tropical Forest & Botanical Garden. Monica, renowned for…
$20
Sid the Bayou Kid at Sloppy Joe’s Bar
Sid the Bayou Kid, a vibrant young musician from Louisiana, captivates audiences at Sloppy Joe's Bar with his bluesy harmonica tunes and storytelling flair. Embracing…
Free
Ross Brown at Rams Head Southernmost
Ross Brown, a versatile musician from Key West, captivates audiences at Rams Head Southernmost with his unique blend of creativity and adventure. Known as a…
Free
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck captivates audiences at Irish Kevin's Bar with his dynamic performances and engaging presence. Bringing a lively mix of music to the heart of…
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
Caleb Tyler at Tiki House Key West
Caleb Tyler brings his dynamic musical talent to Tiki House Key West, enlivening the cozy tiki bar with captivating performances. Known for his engaging presence,…
Free
Shanty Hounds at Rick’s Bar Downstairs Stage
Experience the vibrant acoustic duo Shanty Hounds at Rick's Bar Downstairs Stage in Key West. Dani Hoy and Key West Chris Rehm bring an inventive…
Free
Eric Aardema at Hog’s Breath Saloon
Eric Aardema graces the stage at Hog's Breath Saloon, captivating audiences with his dynamic performances and magnetic presence. In Key West's vibrant Mallory Square District,…
Free
Jefff Clark at Sloppy Joe’s Bar
Jefff Clark is an emerging music artist captivating audiences at Sloppy Joe's Bar, a historic Key West venue. Known for his creativity and innovative sound,…
Free
Oren Polak at Schooner Wharf Bar
Oren Polak graces the stage at Schooner Wharf Bar with his dynamic performances and unique sound, embodying his mission of Music for Everyone, Everywhere. As…
Free
CW Colt at Two Friends Patio Restaurant
Experience the captivating performance of CW Colt at Two Friends Patio Restaurant. Known for his engaging stage presence and exceptional musical talent, CW Colt delights…
Free
Tony Baltimore at Hank’s Hair of the Dog Saloon
Tony Baltimore, a versatile singer/songwriter, enchants audiences with his genre-bending alternative roots-rock at Hank's Hair of the Dog Saloon. Raised by Italian immigrant parents in…
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
Industry Night at The Retro Room
Enjoy a night at The Retro Room in Old Town Key West where entertainment takes center stage. This nostalgic café and restaurant offers a unique…
Free
Joe The Show at Tiki House Key West
Catch Joe The Show at Tiki House Key West, where his dynamic energy and exceptional talent captivate audiences nightly. Known for his tireless work ethic…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin, a charismatic and humor-filled entertainer, brings his laid-back charm to Irish Kevin's Bar in Key West. Known for captivating audiences with his singing…
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
Jesse Lee at Rick’s Bar Downstairs Stage
Catch the vibrant sounds of emerging musician Jesse Lee Jr. at Rick's Bar Downstairs Stage in Key West. Originally from New Jersey, Jesse relocated to…
Free
Cliff Cody at Mac’s Place
Enjoy an unforgettable evening with Cliff Cody at Mac's Place, a vibrant waterfront bar in Key West. The Texas-born, Key West-based indie country singer captivates…
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
Telephone Tag at Hog’s Breath Saloon
Experience the playful antics of Telephone Tag at Hog's Breath Saloon in Key West. This unique entertainer brings humor to the art of communication, engaging…
Free
World Famous 801 Girls- 5pm Show
Experience the dynamic performances of the World Famous 801 Girls at their 5pm show. These talented drag queens captivate audiences with their charisma, artistry, and…
Glow Hours on Hugh’s View
Experience an enchanting evening at Glow Hours on Hugh's View, featuring captivating performances by world-class artists at The Studios of Key West. Set in a…
Jay Klein at Hank’s Hair of the Dog Saloon
Jay Klein, a multifaceted entrepreneur and musician, captivates audiences at Hank's Hair of the Dog Saloon in Key West's Old Town. Known for his innovation…
Free
Zack Seemiller at Rams Head Southernmost
Zack Seemiller, a dynamic musician and performer, captivates audiences with his engaging live shows at Rams Head Southernmost. Known for his motivational prowess, Zack transforms…
Free
Sunset Celebration at Mallory Square
Experience the Sunset Celebration at Mallory Square, a vibrant Key West spectacle where dazzling sunsets meet enthralling entertainment. The famous cat man steals the show…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant energy of Caribe of Key West at El Meson de Pepe's on Mallory Square. This talented entertainer captivates audiences with lively performances,…
Ericson Holt at Two Friends Patio Restaurant
Experience the soulful tunes of Ericson Holt at Two Friends Patio Restaurant. Known for his captivating performances, Holt brings a dynamic blend of blues and…
Free
Tom Petty Night at Green Parrot Bar
Tom Petty Night at Green Parrot Bar promises an electrifying tribute to the legendary rocker. Set in Key West's iconic, lively dive bar, the event…
Free
Jerico Duo at Sloppy Joe’s Bar
Experience the electrifying performance of the Jerico Rockabilly Duo at Sloppy Joe's Bar, an iconic Key West venue. Known for their dynamic rock 'n' roll…
Free
Bo Fodor at RockHouse Live Key West
Bo Fodor brings his innovative artistry and captivating storytelling to RockHouse Live Key West. Known for blending traditional techniques with contemporary ideas, Bo inspires audiences…
Free
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary performer at Irish Kevin’s Bar in Key West. Renowned for his captivating shows, he seamlessly blends music and entertainment, creating…
Free
Happy Dog at The Alamo Key West
Experience the electrifying performance of Happy Dog Band, an improvisational jam band channeling the essence of the psychedelic era, at The Alamo Key West. Known…
Free
Gary Hempsey at Schooner Wharf Bar
Experience the captivating sounds of musician Gary Hempsey at the vibrant Schooner Wharf Bar in Key West. Known for his engaging performances, Gary brings the…
Free
Joe the Show at Rick’s Bar Downstairs Stage
Experience the remarkable talents of Joe The Show at Rick's Bar Downstairs Stage. Known for his dynamic energy and tireless dedication, Joe The Show captivates…
Free
DJ Todd at Red Garter Saloon Stage
Experience the electrifying beats of DJ Todd at the Red Garter Saloon Stage. Known for his innovative and dynamic performances, DJ Todd captivates audiences with…
Free
Gastor Almonte at Comedy Key West
Gastor Almonte, a Dominican-American comedian based in New York City, captivates audiences with his engaging storytelling and warm delivery. Known for blending personal anecdotes with…
$35
Marshall Morlock at Halo Rooftop Lounge Bar at The Saint
Marshall Morlock, the charismatic frontman of The Marshall Morlock Band, is set to captivate audiences at Halo Rooftop Lounge Bar at The Saint. Known for…
Free
Ronnie & Gregory at La Te Da
Ronnie and Gregory light up La Te Da in Key West with their engaging and dynamic performances. Renowned for their vibrant personalities and synergy, the…
Free
Aaron Hudgins at Tiki House Key West
Experience the captivating sounds of musician Aaron Hudgins at Tiki House Key West. Known for his engaging performances, Aaron brings an energetic and soulful vibe…
Free
DJ Duke at Rick’s Bar Upstairs Stage
Experience the electrifying energy of DJ Duke at Rick's Bar Upstairs Stage. Renowned for his dynamic mixes and vibrant performances, DJ Duke captivates audiences with…
Free
Tom Petty Night at Green Parrot Bar
Celebrate Tom Petty Night at the Green Parrot Bar in Key West, a vibrant dive bar bursting with charm and history. Enjoy classic hits and…
Free
Randy Roberts at La Te Da
Randy Roberts at La Te Da is an unparalleled spectacle in Key West's cabaret scene. Renowned for his awe-inspiring live vocals and captivating impersonations of…
$35
Elle Haley at Hank’s Hair of the Dog Saloon
Elle Haley, a vibrant musician from the Florida Keys, captivates audiences with soulful performances at Hank's Hair of the Dog Saloon. Known for her engaging…
Free
Homegrown at Hog’s Breath Saloon
Experience the vibrant sounds of Homegrown at Hog's Breath Saloon, a dynamic country band from Key West, Florida. With heartfelt lyrics and captivating melodies, they…
Free
Karaoke at Bobby’s Monkey Bar
Enjoy a vibrant evening at Bobby's Monkey Bar, nestled in Key West's Old Town. This lively venue offers karaoke nightly, featuring charismatic entertainers who engage…
Tim Bradach at Irish Kevin’s Bar
Tim Bradach captivates audiences at Irish Kevin’s Bar with his energetic performances and musical talent. Known for engaging the crowd, Tim creates an unforgettable night…
Free
Turning The Tide at Sloppy Joe’s Bar
Experience the remarkable journey of Turning The Tide at Sloppy Joe's Bar. This event showcases the entertainer's narrative mastery as they explore themes of resilience…
Free