Wednesday Filet Day at Mary Ellen’s
Every Wednesday, Mary Ellen's in Old Town Key West hosts Filet Day, featuring an exciting lineup of entertainers to enhance your dining experience. Enjoy the…
Free
30 events found.
Events for May 28, 2026
Ongoing
Karaoke at Bobby’s Monkey Bar
Karaoke at Bobby's Monkey Bar features a vibrant island atmosphere in Key West's Old Town. The highlight is the dynamic karaoke sessions led by charismatic…
Kari Wolf at Irish Kevin’s Bar
Kari Wolf, a dynamic musician from Key West, captivates audiences with her soulful melodies and unique style at Irish Kevin's Bar. Her engaging performances bring…
Free
Ambitious Morning Runners
Join the Ambitious Morning Runners at White Street Pier in Key West, where you can start your day with invigorating runs and breathtaking oceanfront views.…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max daily party boat fishing adventure at A & B Marina in Key West's historic seaport. Enjoy a vibrant atmosphere with live…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Enjoy a rejuvenating Yoga on the Beach session at Fort Zachary Taylor in Key West. This historic location offers a unique blend of Civil War…
$20
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga at the breathtaking Key West Tropical Forest & Botanical Garden. Monica, renowned for her transformative yoga sessions,…
$20
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O'Maolain captivates audiences at Irish Kevin's Bar with his energetic performances and engaging stage presence. Known for his lively tunes and magnetic charisma, Mylo…
Free
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant nightlife atmosphere at Key West First Legal Rum Distillery. Enjoy free daily tours and tastings in this historic seaport location, once a…
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 of four people for an unforgettable experience. Enjoy lively entertainment as expert…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the Glass Bottom Boat Cruise in Key West, where a charming entertainer guides you through the vibrant marine life visible beneath your feet. With…
$69.95
Truman Waterfront Farmers Market
Every week, the Truman Waterfront Farmers Market in Key West buzzes with excitement as visitors enjoy lively performances from talented entertainers. Set against the stunning…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West where the stars of the show are the vibrant marine life visible through the crystal-clear…
$69.95
Irish Kevin at Irish Kevin’s Bar
Irish Kevin, the charismatic entertainer at Irish Kevin’s Bar in Key West, is renowned for his engaging performances. With a laid-back style and infectious humor,…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join Sunset Watersports in Key West's Historic Seaport for an unforgettable adventure. Although details about the entertainer are sparse, the experienced staff ensures a thrilling…
$79.95
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join us for the Glass Bottom Boat Cruise in Key West, a unique journey showcasing the magical underwater world. Delight in live entertainment that enhances…
$69.95
World Famous 801 Girls- 5pm Show
Experience the dazzling spectacle of the World Famous 801 Girls at their 5pm show. These renowned entertainers captivate audiences with their charisma and vibrant performances…
Sunset Celebration at Mallory Square
Experience the lively Sunset Celebration at Mallory Square in Key West. As the sun dips below the horizon, be captivated by enchanting street performers like…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West, a dynamic entertainer, captivates audiences at El Meson de Pepe’s on Mallory Square. Known for their vibrant performances, Caribe infuses the…
Tony Baltimore Record Release Party with Conch Town Records at Green Parrot Bar
Join Tony Baltimore at the Green Parrot Bar for his dynamic record release party with Conch Town Records. Experience his genre-bending alternative roots-rock as he…
Free
Bria Ansara at Berlin’s Cocktail Bar
Experience the mesmerizing talent of Bria Ansara at Berlin's Cocktail Bar, where her captivating jazz performances enhance the venue's nostalgic ambiance. Nestled within the historic…
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
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
Catch The Mania Trivia at Brady’s Pub
Immerse yourself in a thrilling evening hosted by the captivating entertainer at Brady's Pub's Catch The Mania Trivia night. Set in the vibrant atmosphere of…
Free
Andy’s Cabana Open Mic No Mic Night
Experience an unforgettable evening at Andy's Cabana Open Mic No Mic Night, where talented local entertainers shine without amplification. Set in the vibrant ambiance of…
Free
Tony Baltimore Record Release Party with Conch Town Records at Green Parrot Bar
Join Tony Baltimore at the Green Parrot Bar for his dynamic record release party with Conch Town Records. Experience his genre-bending alternative roots-rock as he…
Free
Karaoke with Foss at RockHouse Live
Join Foss for an unforgettable karaoke night at RockHouse Live Key West, where his charisma and engaging presence light up the stage. Experience a lively…
Free
Karaoke at Bobby’s Monkey Bar
Experience the vibrant energy of Karaoke at Bobby's Monkey Bar, where the star is the charismatic karaoke host who engages the lively crowd. Located in…
Tony Baltimore Record Release Party with Conch Town Records at Green Parrot Bar
Join Tony Baltimore at the Green Parrot Bar for his dynamic record release party with Conch Town Records. Experience his genre-bending alternative roots-rock as he…
Free
Riptide Riot at Irish Kevin’s Bar
Riptide Riot, the dynamic power duo from Key West, captivates audiences every week at Irish Kevin's Bar. Featuring Jim Simonian on drums and vocals and…
Free