Karaoke with Foss at RockHouse Live
Join Foss for an unforgettable karaoke night at RockHouse Live Key West. Known for his vibrant energy and engaging performances, Foss transforms the venue into…
Free
28 events found.
Events for May 8, 2026
Ongoing
Karaoke at Bobby’s Monkey Bar
Experience a vibrant night of entertainment at Bobby's Monkey Bar in Key West's Old Town. The highlight is the dynamic karaoke sessions led by a…
Riptide Riot at Irish Kevin’s Bar
Experience the electrifying performance of Riptide Riot, a dynamic power duo at Irish Kevin's Bar in Key West. With Jim Simonian on drums and vocals…
Free
Yoga on the Beach – Smather’s Beach
Join the invigorating Yoga on the Beach at Smather's Beach, where the serene ocean backdrop enhances your experience. Led by a dynamic and inspiring instructor,…
$20
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
Experience the serene practice of Yoga on the Beach at Fort Zachary Taylor State Park. This event combines the tranquil surroundings of a historic Civil…
$20
Story Time at the Key West Library
Join Story Time at the Key West Library where a captivating storyteller brings tales to life, enchanting children and adults alike. Nestled in the historic…
Free
Jeff Harris at Irish Kevin’s Bar
Experience the dynamic talents of Jeff Harris at Irish Kevin's Bar in Key West. As a singer, songwriter, comedian, and author, Jeff captivates audiences with…
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
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Experience the captivating performance of Caleb Hogan at A Pirate Looks Back: Jimmy Buffett Tribute Show in Comedy Key West. As a skilled musician, actor,…
$28
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
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O'Maolain captivates audiences at Irish Kevin's Bar with his dynamic performances, blending traditional Irish tunes and modern hits. Known for engaging with the crowd,…
Free
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for a thrilling daily party boat fishing adventure at A & B Marina in Key West's historic seaport. While enjoying the vibrant…
$85.00
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
The World Famous 801 Girls light up the stage at 801 Bourbon Bar in Key West's vibrant nightlife scene. Known for their dazzling and energetic…
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience an unforgettable evening with Caribe of Key West at El Meson de Pepe on Mallory Square. This family-owned Cuban restaurant offers more than just…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square in Key West, where talented street performers captivate audiences daily. Amid stunning ocean sunsets, watch jugglers and…
Free
Jason Ricci & The Bad Kind at Green Parrot Bar
Experience the electrifying performance of Jason Ricci & The Bad Kind at the iconic Green Parrot Bar in Key West. Known for his harmonica virtuosity…
Free
NY Pauly at Irish Kevin’s Bar
NY Pauly, a legendary performer at Irish Kevin's Bar in Key West, captivates audiences with his seamless blend of music and entertainment. Known for his…
Free
Karaoke at Two Friends Patio
Experience a lively night of karaoke at Two Friends Patio Restaurant, a Key West favorite since 1967. The highlight is the charismatic entertainer who keeps…
Free
Eddie Gossling at Comedy Key West
Eddie Gossling brings his seasoned comedic flair to Comedy Key West, captivating audiences with his sharp wit and engaging storytelling. With over 20 years in…
$35
Jason Ricci & The Bad Kind at Green Parrot Bar
Experience the electrifying energy of Jason Ricci & The Bad Kind at the iconic Green Parrot Bar in Key West. Known for his dynamic harmonica…
Free
Karaoke at Bobby’s Monkey Bar
Karaoke at Bobby's Monkey Bar is a vibrant event featuring an exceptional entertainer who brings energy and excitement to the lively island atmosphere of Key…
Riptide Riot at Irish Kevin’s Bar
Riptide Riot, a dynamic power duo from Key West, electrifies Irish Kevin's Bar with their high-energy, all-request rock show. Comprised of Jim Simonian on drums…
Free
Jason Ricci & The Bad Kind at Green Parrot Bar
Experience the electrifying performance of Jason Ricci & The Bad Kind at the iconic Green Parrot Bar in Key West. Known for his exceptional harmonica…
Free