Karaoke at Bobby’s Monkey Bar
Join the vibrant atmosphere at Bobby's Monkey Bar in Key West for an unforgettable evening of karaoke. Enjoy captivating performances by talented entertainers as they…
21 events found.
Events for May 27, 2026
Ongoing
Simonian Wolf at Irish Kevin’s Bar
Simonian Wolf brings an electrifying presence to Irish Kevin’s Bar in Key West. Known for their charisma and innovative flair, Wolf captivates audiences through an…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max for a daily party boat fishing adventure at A & B Marina in Key West. While the marina offers excellent boating…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Join celebrated instructor Sarah Martinez for Yoga on the Beach at Fort Zachary Taylor State Park in Key West. Experience a rejuvenating session surrounded by…
$20
Aqua Yoga at Southernmost Beach Resort
Experience tranquility and rejuvenation with Aqua Yoga at Southernmost Beach Resort. Set amidst lush gardens and ocean views, this session offers a unique blend of…
$20
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
Distillery Tour – Key West Legal Rum Distillery
Explore the captivating Key West Legal Rum Distillery located in the Historic Seaport, offering an engaging atmosphere with daily free tours and tastings. Delight in…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at the Key West Legal Rum Distillery, where a talented entertainer guides you through the art of crafting the perfect mojito.…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West for a captivating evening of ocean exploration. Highlighting a talented entertainer, the cruise combines marine beauty…
$69.95
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
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West for an unforgettable journey with spectacular views of marine life. The highlight of the cruise is…
$69.95
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck captivates audiences at Irish Kevin's Bar with his engaging performances and vibrant energy. As a talented musician, he brings live music to life,…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience an unforgettable aquatic adventure with Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise at Sunset Watersports in Key West. Dive into vibrant coral…
$79.95
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West and enjoy the mesmerizing views of the ocean beneath you, all while being entertained by talented…
$69.95
World Famous 801 Girls- 5pm Show
Experience the dazzling World Famous 801 Girls at the 5pm show, where these talented drag queens mesmerize audiences with their sensational performances. Located at 801…
Sunset Celebration at Mallory Square
At the Sunset Celebration at Mallory Square, entertainment steals the show with a dynamic lineup of street performers and the legendary cat man captivating audiences.…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the enchanting entertainment at El Meson de Pepe's on Mallory Square, featuring the dynamic Caribe of Key West. This vibrant performance, set against the…
Irish Kevin at Irish Kevin’s Bar
Irish Kevin is a charismatic entertainer who brings humor and charm to Irish Kevin's Bar in Key West. Known for captivating audiences with his laid-back…
Free
Line Dancing at Kaya Island Eats
Join the fun at Kaya Island Eats in Key West for an unforgettable line dancing experience. With a vibrant Caribbean atmosphere, this local gem offers…
Free
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