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
22 events found.
Events for May 19, 2026
Ongoing
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 brings a dynamic and unforgettable performance to Irish Kevin's Bar. An Irish-born musician, he captivates audiences with his unique blend of traditional Irish…
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 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 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
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
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck brings his vibrant musical talent to Irish Kevin’s Bar in the heart of Old Town Key West. Known for electrifying performances that engage…
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
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
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
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
Irish Kevin at Irish Kevin’s Bar
Irish Kevin is a laid-back and fun-loving entertainer renowned for his charm and humor at Irish Kevin’s Bar in Key West. His genuine spirit and…
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
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
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…
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…
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary performer captivating audiences at Irish Kevin's Bar in Key West. Known for his dynamic shows, he seamlessly blends music and…
Free
Comedy Key West Open Mic at Comedy Key West
Join Comedy Key West Open Mic for a dynamic night of laughter and creativity, where both budding comedians and seasoned performers take the stage. Revel…
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…
Simonian Wolf at Irish Kevin’s Bar
Simonian Wolf captivates audiences at Irish Kevin's Bar with their charismatic presence and multifaceted talents. Known for their passion for innovation and creative problem-solving, they…
Free