Martini Monday at Virgilios
Martini Monday at Virgilios in Old Town Key West offers an enchanting evening filled with live music that captivates the audience. As you savor premier…
Free
64 events found.
Events for April 21, 2026
Ongoing
DJ Marty at Red Garter Saloon Stage
Experience the electrifying beats of DJ Marty at the Red Garter Saloon Stage in Key West. Known for his innovative mixing and dynamic performances, DJ…
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 mesmerizing mixes and vibrant stage presence, DJ Duke captivates audiences…
Free
HYPER DRIVE at Durty Harry’s Stage
Experience the electrifying performance of Hyper Drive at Durty Harry's Stage. This dynamic entertainer, known for his captivating vocals and guitar prowess, delivers powerful melodies…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience the electrifying energy of the Alex Anthony Band at Hog's Breath Saloon in Key West. Renowned for reinventing the modern cover band experience, Alex…
Free
Karaoke at Bobby’s Monkey Bar
Experience a vibrant night at Bobby's Monkey Bar in Key West's Old Town, featuring karaoke nightly in a lively island atmosphere. Though the entertainer details…
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O’Maolain captivates audiences at Irish Kevin's Bar with his dynamic performances and engaging charisma. Known for his lively music and infectious energy, Mylo creates…
Free
Radio Hero at Sloppy Joe’s Bar
Experience the electrifying energy of Radio Hero at Sloppy Joe's Bar. Known for their explosive party rock performances, Radio Hero captivates audiences with their dynamic…
Free
Ambitious Morning Runners
Ambitious Morning Runners at White Street Pier in Key West is a vibrant event that captures the essence of oceanfront beauty. While the scenic locale…
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 serenity with Yoga on the Beach at Fort Zachary Taylor State Park in Key West. Immerse yourself in nature's tranquility as an expert instructor…
$20
Jonathan Williams at Two Friends Patio Restaurant
Jonathan Williams captivates audiences at Two Friends Patio Restaurant with his soulful melodies and engaging performances. As a talented musician, he enhances the vibrant atmosphere…
Free
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga, a rejuvenating experience set amidst the lush surroundings of the Key West Tropical Forest & Botanical Garden.…
$20
Joe The Show at Sloppy Joe’s Bar
Experience the dynamic energy of Joe The Show at Sloppy Joe's Bar, where his exceptional talent captivates audiences daily. Known as JTS, Joe is celebrated…
Free
Ross Brown at Rams Head Southernmost
Ross Brown, a versatile musician from Key West, brings his dynamic energy and adventurous spirit to Rams Head Southernmost. Known as a Spiritual Gangster, his…
Free
Bradd Shadduck at Irish Kevin’s Bar
At Irish Kevin's Bar, Bradd Shadduck energizes the crowd with his captivating performances. As a skilled musician, he engages the audience in the lively atmosphere…
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
Caleb Tyler at Tiki House Key West
Experience an unforgettable evening with Caleb Tyler at Tiki House Key West. Known for his captivating performances, Caleb brings a unique blend of energy and…
Free
Shanty Hounds at Rick’s Bar Downstairs Stage
Experience the dynamic energy of Shanty Hounds, a lively acoustic duo based in Key West, at Rick's Bar Downstairs Stage. Comprised of Dani Hoy and…
Free
Barrett Thomas at Hog’s Breath Saloon
Barrett Thomas is a dynamic musician known for his innovative looping techniques and captivating performances at Hog's Breath Saloon in Key West. His vibrant energy…
Free
Ross Brown at Sloppy Joe’s Bar
Ross Brown, a dynamic musician from Key West, captivates audiences at Sloppy Joe's Bar with his unique blend of creativity and adventure. Infused with a…
Free
Oren Polak at Schooner Wharf Bar
Oren Polak, a versatile musician and band leader, captivates audiences at Schooner Wharf Bar with his unique sound and charisma. Known for his engaging performances,…
Free
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
CW Colt at Two Friends Patio Restaurant
Experience the captivating performance of CW Colt at Two Friends Patio Restaurant, a vibrant live music venue in Key West. Known for his dynamic musical…
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
Industry Night at The Retro Room
Experience Industry Night at The Retro Room in Old Town Key West, where nostalgia meets entertainment in a vibrant setting. While the event details are…
Free
Joe The Show at Tiki House Key West
Experience the electrifying talent of Joe The Show at Tiki House Key West. Known for his dedication and passion, Joe captivates audiences with his dynamic…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin, a beloved figure at Irish Kevin's Bar in Key West, is renowned for his laid-back, fun-loving nature and captivating charm. With his humor…
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
Jesse Lee at Rick’s Bar Downstairs Stage
Catch the rising star Jesse Lee Jr at Rick's Bar Downstairs Stage in Key West, where his passion for music shines. Originally from New Jersey,…
Free
Cliff Cody at Mac’s Place
Experience the captivating performance of Cliff Cody at Mac's Place. A Texas-born, Key West-based indie country singer/songwriter, Cody is renowned for his powerful voice and…
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
Ross Brown Duo at Hog’s Breath Saloon
Experience the vibrant performance of the Ross Brown Duo at Hog's Breath Saloon. Ross Brown, a dynamic Key West musician known for his adventurous spirit…
Free
World Famous 801 Girls- 5pm Show
Experience the unparalleled talent of the World Famous 801 Girls at their 5pm show. Known for their dynamic performances and captivating presence, these drag queens…
Glow Hours on Hugh’s View
Experience captivating performances at Glow Hours on Hugh's View, located at The Studios of Key West. This prime cultural venue presents a fusion of world-class…
Zack Seemiller at Rams Head Southernmost
At Rams Head Southernmost, enjoy an unforgettable performance by Zack Seemiller, a dynamic musician and songwriter. Known for his engaging presence and motivational speaking, Zack…
Free
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is an unforgettable experience, showcasing breathtaking sunsets and vibrant street performances. The highlight is the entertainment,…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant melodies of Caribe of Key West at El Meson de Pepes on Mallory Square. This family-owned Cuban restaurant offers not only authentic…
Ericson Jolt at Two Friends Patio Restaurant
Experience the vibrant sounds of Ericson Holt at Two Friends Patio Restaurant. Known for his captivating performances, Ericson brings a unique blend of musical talent…
Free
Claire Finley and Dave Scher at Green Parrot Bar
Claire Finley and Dave Scher bring their exceptional musical talents to the iconic Green Parrot Bar in Key West. Known for their electrifying performances, Claire…
Free
Jefff Clark Band at Sloppy Joe’s Bar
Immerse yourself in the lively atmosphere of Sloppy Joe's Bar with the Jefff Clark Band. Jefff Clark, an emerging music artist known for his creativity…
Free
Bo Fodor at RockHouse Live Key West
Experience the captivating artistry of Bo Fodor at RockHouse Live Key West. Renowned for his innovative approach and passion for storytelling, Bo combines traditional techniques…
Free
Happy Dog at The Alamo Key West
Experience the exhilarating performances of Happy Dog Band at The Alamo Key West. Known for their improvisational jam sessions, this psychedelic rock band captivates audiences…
Free
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary performer at Irish Kevin's Bar in Key West, captivating audiences with his seamless blend of music and entertainment. His vibrant…
Free
Havana Nights Salsa Dancing Lessons!
Immerse yourself in the rhythm of Havana Nights Salsa Dancing Lessons every Tuesday at Southernmost Beach Resort. Let our talented entertainers guide you through electrifying…
Free
Gary Hempsey at Schooner Wharf Bar
Enjoy an unforgettable evening with musician Gary Hempsey at the renowned Schooner Wharf Bar. Known for his captivating performances, Gary brings vibrant energy and soulful…
Free
Joe the Show at Rick’s Bar Downstairs Stage
Experience the magnetic charm of Joe The Show at Rick's Bar Downstairs Stage. Known for his relentless dedication and vibrant performances, JTS captivates with unmatched…
Free
DJ Todd at Red Garter Saloon Stage
DJ Todd, an innovative DJ known for his eclectic mixes and dynamic performances, commands the Red Garter Saloon Stage with his unique soundscapes. His energetic…
Free
Comedy Key West Open Mic at Comedy Key West
Join Comedy Key West's Open Mic Night for an exhilarating evening of laughter and creativity. This vibrant event invites both novice comedians and seasoned performers…
Free
Jack Wolf at Halo Rooftop Lounge Bar at The Saint
Jack Wolf, a renowned singer-songwriter from Key West, enchants audiences at the Halo Rooftop Lounge Bar with his soulful performances. Known for his captivating melodies…
Free
Ronnie & Gregory at La Te Da
Experience the captivating energy of Ronnie and Gregory at La Te Da, where their dynamic personalities and creative synergy light up the stage. This talented…
Free
Aaron Hudgins at Tiki House Key West
Experience the charismatic performance of Aaron Hudgins at Tiki House Key West. As a talented musician, Hudgins brings vibrant energy and soulful melodies to this…
Free
DJ Duke at Rick’s Bar Upstairs Stage
DJ Duke is a dynamic music producer renowned for his mesmerizing mixes and electrifying performances. Known for blending genres with a vibrant stage presence, he…
Free
LUVBOM at Durty Harry’s Stage
Experience the electrifying energy of LUVBOM at Durty Harry's Stage in Key West. This dynamic performer captivates audiences with his vocal prowess and guitar skills.…
Free
Claire Finley and Dave Scher at Green Parrot Bar
Claire Finley and Dave Scher bring vibrant energy to the Green Parrot Bar, captivating audiences with their electrifying performances. Known for their skillful musical prowess,…
Free
Randy Roberts at La Te Da
Randy Roberts is a captivating performer at La Te Da's cabaret in Key West, celebrated for his electrifying vocals and iconic impersonations of legends like…
$35
CAPTAINS’ MEETING – INDEPENDENCE NAVAL PARADES
Join the captivating event at Schooner Wharf Bar for the CAPTAINS’ MEETING - INDEPENDENCE NAVAL PARADES, featuring live music that embodies the laid-back island vibe…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience the Alex Anthony Band at Hog's Breath Saloon, where Alex Anthony redefines the cover band scene. Known for their electrifying performances and unique blend…
Free
Karaoke at Bobby’s Monkey Bar
Enjoy a vibrant evening of karaoke at Bobby's Monkey Bar in Key West's Old Town. This lively venue features talented local entertainers who bring excitement…
Radio Hero at Sloppy Joe’s Bar
Radio Hero energizes Sloppy Joe's Bar with their explosive and edgy party rock performances. Known for their dynamic sound and bold stage presence, this band…
Free
Simonian Wolf at Irish Kevin’s Bar
Simonian Wolf graces Irish Kevin's Bar with their captivating presence, blending diverse talents to create an unforgettable experience. Known for their charismatic charm and strategic…
Free
Karaoke w/ Jorge at Rick’s Bar Downstairs Stage
Join DJ Jorge for an electrifying karaoke night at Rick's Bar Downstairs Stage. Known for his vibrant performances and energetic beats, DJ Jorge keeps the…
Free