Wednesday Filet Day at Mary Ellen’s
Join the lively atmosphere at Mary Ellen's in Old Town Key West for Wednesday Filet Day. Enjoy classic American comfort food, including mouthwatering gourmet grilled…
Free
75 events found.
Events for April 16, 2026
Ongoing
DJ Todd at Red Garter Saloon Stage
Experience the electrifying talents of DJ Todd at the Red Garter Saloon Stage. Known for his innovative mixes and dynamic performances, DJ Todd captivates audiences…
Free
DJ Duke at Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Duke at Rick's Bar Upstairs Stage. Renowned for his dynamic and innovative music production, DJ Duke captivates global audiences…
Free
Crank Sinatra at Durty Harry’s Stage
Experience the electrifying energy of Krank Sinatra, a multi-talented musician in Key West, at Durty Harry's Stage. Known for his dynamic performances, Krank Sinatra captivates…
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 an unforgettable evening at Bobby's Monkey Bar, where the charismatic karaoke host steals the show. With their energetic presence, they turn every night into…
Tim Bradach at Irish Kevin’s Bar
Tim Bradach captivates audiences at Irish Kevin's Bar with his engaging performances. Known for his dynamic presence, he seamlessly blends a variety of musical genres,…
Free
Turning The Tide at Sloppy Joe’s Bar
Experience the captivating narrative of Turning The Tide at Sloppy Joe's Bar in Key West. This inspiring storyteller takes you on a transformative journey of…
Free
Karaoke w/ Davis at Rick’s Bar Downstairs Stage
Join the electrifying DJ Davis for an unforgettable night of karaoke at Rick's Bar Downstairs Stage. Known for his eclectic mix and infectious energy, Davis…
Free
Ambitious Morning Runners
The Ambitious Morning Runners event at White Street Pier in Key West features live entertainment against a stunning oceanfront backdrop. As runners gather to experience…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max for a memorable daily party boat fishing adventure departing from A & B Marina in Key West's historic seaport. Experience lively…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Experience tranquility at Yoga on the Beach with renowned instructor in the serene setting of Fort Zachary Taylor State Park, Key West. Enjoy a unique…
$20
Alfonse at Two Friends Patio Restaurant
Alfonse captivates audiences with his dynamic performances at Two Friends Patio Restaurant. Known for creating an enchanting atmosphere, he enhances the island dining experience with…
Free
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga at the Key West Tropical Forest & Botanical Garden. Monica brings her expertise to this serene setting,…
$20
Justin Angelo at Sloppy Joe’s Bar
Experience the captivating performances of Justin Angelo at Sloppy Joe's Bar, an iconic Key West venue. A versatile musician and songcrafter, Justin draws inspiration from…
Free
Robert Douglas at Rams Head Southernmost
Experience the captivating performance of Robert Douglas at Rams Head Southernmost. Known for his soulful melodies and dynamic stage presence, Robert enchants audiences in this…
Free
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O’Maolain captivates crowds at Irish Kevin’s Bar with his dynamic performances and engaging stage presence. Known for his unique blend of traditional and contemporary…
Free
Trenton Chandler at Rick’s DownStairs Stage
Trenton Chandler, a talented country musician hailing from Shallowater, Texas, brings his heartfelt compositions to Rick's DownStairs Stage. Inspired by West Texas legends like Buddy…
Free
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant nightlife atmosphere at Key West First Legal Rum Distillery in the Historic Seaport. Enjoy daily free tours, rum samples, and mojito-making classes.…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West Legal Rum Distillery, where a charismatic entertainer guides you through the art of crafting the perfect mojito. Set…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Explore the vibrant marine life of the Florida Keys on the Glass Bottom Boat Cruise, departing from Fury Key West. This captivating experience promises unforgettable…
$69.95
Dan Harvey at Hog’s Breath Saloon
Dan Harvey captivates audiences at Hog's Breath Saloon in Key West with his versatile musical talents. Known for his unique live music and DJ hybrid…
Free
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan brings his musical talent to the iconic Sloppy Joe's Bar in Key West. Known for electrifying performances, Tim captivates audiences with his dynamic…
Free
Ross Brown at Schooner Wharf Bar
Ross Brown is a talented musician based in Key West, Florida, known for his dynamic performances at Schooner Wharf Bar. Embracing a lifestyle infused with…
Free
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
At A Pirate Looks Back: Jimmy Buffett Tribute Show, acclaimed performer Caleb Hogan captures the essence of legendary musician Jimmy Buffett. With his vibrant portrayal…
$28
Shanty Hounds at Two Friends Patio Restaurant
Shanty Hounds, the dynamic acoustic duo of Dani Hoy and Key West Chris Rehm, brings infectious joy to Two Friends Patio Restaurant. Known for their…
Free
Truman Waterfront Farmers Market
At Truman Waterfront Farmers Market in Key West, enjoy lively performances at the amphitheater amidst a vibrant community setting. While vibrant stalls offer local produce…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the mesmerizing Glass Bottom Boat Cruise in Key West, featuring a captivating entertainer who brings the marine wonders to life. Depart from Fury Key…
$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 with engaging visuals and…
Free
Just George at The Alamo Key West
Experience the soulful tunes of Just George at The Alamo in Key West, where he brings his heartfelt acoustic performances to life. This passionate local…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin, a charismatic and humorous entertainer, captivates audiences at Irish Kevin's Bar in Key West. Known for his laid-back charm and engaging performances, he…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience the ultimate aquatic adventure with Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise at Sunset Watersports, Key West. Guided by skilled entertainers, explore…
$79.95
Jeff Harris at Rick’s Bar Downstairs
Enjoy an unforgettable evening with Jeff Harris at Rick's Bar Downstairs in Key West. A singer, songwriter, comedian, and author, Jeff captivates audiences with his…
Free
Collette Campbell at Mac’s Place
Collette Campbell, a gifted singer-songwriter from Long Island, brings her NYC musical theatre flair to Key West's Mac's Place. Leading her band, CC and The…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise from Key West with a stellar entertainer elevating the journey. Enjoy captivating commentary and lively performances as you…
$69.95
Telephone Tag at Hog’s Breath Saloon
Experience the lively tunes of Telephone Tag at Hog's Breath Saloon. Known for their unique twist on playful communication, the entertainer brings a fun, engaging…
Free
World Famous 801 Girls- 5pm Show
Experience the captivating World Famous 801 Girls at their 5pm show, where talented drag queens dazzle the stage with charisma and flair. Held at 801…
Ice Society Ice Bath Thursdays
Join Ice Society Ice Bath Thursdays at Kava Culture, Key West, for an invigorating experience. Alongside ice baths and conscious conversations, enjoy the vibrant atmosphere…
Free
Elle Haley at Hank’s Hair of the Dog Saloon
Elle Haley, a dynamic musician from the Florida Keys, captivates audiences with her soulful performances at Hank's Hair of the Dog Saloon. Known for her…
Free
Micah Read at Rams Head Southernmost
Micah Read captivates audiences at Rams Head Southernmost with his soulful and dynamic performances, blending a variety of musical styles. His engaging stage presence and…
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 Pepes on Mallory Square. This captivating entertainer brings the spirit of Cuban…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square in Key West where talented street performers take center stage. Revel in the artistry of jugglers and…
Free
Ericson Holt at Two Friends Patio Restaurant
Experience the captivating performances of Ericson Holt at Two Friends Patio Restaurant. Known for his dynamic musical talent, Ericson's live shows create an enchanting atmosphere…
Free
AstroYeti at Green Parrot Bar
AstroYeti brings an electrifying performance to the iconic Green Parrot Bar in Key West, captivating audiences with their dynamic sound and vibrant energy. Known for…
Free
Preacher Pete Presents at Sloppy Joe’s Bar
Experience the captivating presence of Preacher Pete at Sloppy Joe's Bar, where his warm demeanor and insightful storytelling illuminate the vibrant, historic venue. Known for…
Free
Bria Ansara at Berlin’s Cocktail Bar
Bria Ansara enchants patrons at Berlin's Cocktail Bar with her captivating performance. Her jazz-infused vocals and magnetic stage presence create an unforgettable experience. As guests…
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 Waynard Scheller for an unforgettable evening at Viva Argentinian Steakhouse, where his exceptional keyboard skills and vibrant stage presence with Rainbow Full of Sound…
Free
April’s Walk On White
April's Walk On White features captivating live music, creating a dynamic atmosphere for this monthly art walk. Held along picturesque White Street in Key West,…
Free
Barrett Thomas at The Alamo Key West
Barrett Thomas is a dynamic musician based in Key West, renowned for his innovative live performances. Using his talent as a looper, he creates captivating…
Free
Oren Polak at Irish Kevin’s Bar
Oren Polak captivates audiences at Irish Kevin's Bar with his versatile music and charismatic stage presence. Known for delivering Music for Everyone, Everywhere, his performances…
Free
Terri, Larry and Friends Live Music at William Weech American Legion Post 168
Terri, Larry, and Friends deliver electrifying performances at the William Weech American Legion Post 168 in Key West. Known for their dynamic stage presence, this…
Free
Catch The Mania Trivia at Brady’s Pub
Join the excitement at Brady's Pub for Catch The Mania Trivia, hosted by a dynamic entertainer who brings energy and fun to every question. Enjoy…
Free
Wicked Bingo at The Retro Room
Experience a captivating evening with the lively entertainer at Wicked Bingo in The Retro Room, nestled in Old Town Key West. This nostalgic venue offers…
Free
Andy’s Cabana Open Mic No Mic Night
Andy's Cabana showcases a unique night where talented performers captivate audiences in an intimate environment, relying solely on their pure acoustic sounds. Nestled in Key…
Free
Joe The Show at Rick’s Bar Downstairs Stage
Experience the magic of Joe The Show, the hardest working musician in Key West, live at Rick's Bar Downstairs Stage. JTS captivates audiences with his…
Free
Nick Brownell at Schooner Wharf Bar
Nick Brownell is a talented musician known for his captivating live performances at Schooner Wharf Bar. His diverse musical repertoire enchants audiences every Thursday evening…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at the Schooner Wharf Bar in Key West. Celebrated for his innovative illusions and captivating storytelling, Everhart mesmerizes…
Free
DJ Marty at Red Garter Saloon Stage
Experience the electrifying energy of DJ Marty at the Red Garter Saloon Stage. Known for his dynamic mixing skills and innovative music curation, DJ Marty…
Free
Kristen McNamara at La Te Da
Kristen McNamara, a multifaceted artist, enchants audiences at La Te Da in Key West with her soulful singing and evocative songwriting. Inspired by her love…
Free
Zach Lovering at Halo Rooftop Lounge Bar at The Saint
Zach Lovering captivates audiences at the Halo Rooftop Lounge Bar in The Saint Hotel with his vibrant performances and soulful melodies. A beloved local musician…
Free
Tony Baltimore at Tiki House Key West
Experience the musical artistry of Tony Baltimore at Schooner Wharf Bar in Key West. This talented singer/songwriter blends alternative roots-rock with captivating originality. Raised by…
Free
DJ Chaka at Rick’s Bar Upstairs Stage
Experience the dynamic beats of DJ Chaka at Rick's Bar Upstairs Stage in Key West. A lively entrepreneur and cancer survivor, DJ Chaka channels his…
Free
AstroYeti at Green Parrot Bar
AstroYeti takes the stage at the iconic Green Parrot Bar in Key West, bringing their unique blend of cosmic sounds to this historic dive bar.…
Free
Amos Gill at Comedy Key West
Amos Gill, a standout Australian comedian, brings his sharp wit and engaging storytelling to Comedy Key West. Known for captivating audiences with hilarious insights and…
$35
Durtbags at Durty Harry’s Stage
Experience the ultimate party with The Durtbags, Key West's premier rock band, at Durty Harry's Stage. Performing live every Thursday through Sunday, their energetic shows…
Free
Randy Roberts at La Te Da
Experience the unparalleled talent of Randy Roberts at La Te Da's cabaret. With over thirty years of captivating performances, Randy's live vocals and charismatic stage…
$35
Elle Haley & the Why Nots at General Horseplay
Elle Haley, a vibrant musician from the Florida Keys, brings her captivating performances to General Horseplay. Known for soulful tunes, Elle offers audiences a musical…
Free
Homegrown at Hog’s Breath Saloon
Homegrown is a dynamic country band originating from Key West, Florida, captivating audiences with heartfelt lyrics and engaging melodies. Performing live at Hog's Breath Saloon,…
Free
Karaoke with Foss at RockHouse Live
Join Foss for an electrifying night of karaoke at RockHouse Live in Key West. Known for his dynamic stage presence, Foss elevates the karaoke experience,…
Free
Karaoke at Bobby’s Monkey Bar
Enjoy electrifying evenings with top-notch entertainers at Bobby's Monkey Bar's karaoke nights. Nestled in Key West's Old Town, the bar boasts a lively island atmosphere…
Turning The Tide at Sloppy Joe’s Bar
At Sloppy Joe's Bar, Turning The Tide captivates audiences with a powerful narrative of resilience and determination. This transformative performance explores personal and social challenges,…
Free
AstroYeti at Green Parrot Bar
AstroYeti brings a cosmic blend of energetic beats and vibrant melodies to the iconic Green Parrot Bar in Key West. Known for electrifying performances, AstroYeti…
Free
Tim Bradach at Irish Kevin’s Bar
Experience the vibrant energy of Tim Bradach at Irish Kevin's Bar, where his captivating performances bring the venue to life. As a talented musician, Tim…
Free
Karaoke w/ Jason at Rick’s Bar Downstairs Stage
Join DJ Jason at Rick's Bar Downstairs Stage for an unforgettable karaoke night. Renowned for his electrifying beats and seamless mixing, Jason captivates audiences with…
Free