Wednesday Filet Day at Mary Ellen’s
Mary Ellen's Wednesday Filet Day is a must-visit in Old Town Key West, where the lively atmosphere pairs perfectly with live music from talented local…
Free
29 events found.
Events for May 21, 2026
Ongoing
Karaoke at Bobby’s Monkey Bar
Enjoy a vibrant night of music at Bobby's Monkey Bar in Key West's Old Town. Experience the lively island atmosphere as entertainers bring the karaoke…
Kari Wolf at Irish Kevin’s Bar
Experience the enchanting melodies of Kari Wolf at Irish Kevin's Bar in Key West. This dynamic musician captivates audiences with her soulful performances, creating a…
Free
Ambitious Morning Runners
Join the Ambitious Morning Runners event at White Street Pier in Key West, a picturesque location ideal for early risers. Enjoy breathtaking ocean views as…
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 tranquility with Yoga on the Beach at Fort Zachary Taylor State Park. Immerse yourself in a serene environment while practicing yoga with expert guidance.…
$20
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga at the stunning Key West Tropical Forest & Botanical Garden. Monica, an experienced yoga instructor, guides participants…
$20
Mylo O’Maolain at Irish Kevin’s Bar
Experience the electrifying performance of Mylo O’Maolain at Irish Kevin’s Bar, where his energetic tunes captivate audiences in the bustling heart of Old Town Key…
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
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Experience the captivating talents of Caleb Hogan as he embodies Jimmy Buffett in A Pirate Looks Back at Comedy Key West. This lunch theater tribute…
$28
Truman Waterfront Farmers Market
The Truman Waterfront Farmers Market in Key West is a lively event held at Truman Waterfront Park, featuring local food and crafts. A key highlight…
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
Irish Kevin at Irish Kevin’s Bar
Irish Kevin is a charismatic entertainer known for his charm and humor at Irish Kevin's Bar in Key West. With a genuine spirit, he captivates…
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
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
World Famous 801 Girls- 5pm Show
Experience the dazzling talent of the World Famous 801 Girls in their 5pm show at the 801 Bourbon Bar. Renowned for their captivating performances, these…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square, where the true stars are the street performers. Be captivated by jugglers and the renowned cat man…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the lively sounds of Caribe at El Meson de Pepes on Mallory Square in Key West. This vibrant Cuban restaurant, known for its rich…
Walk on White
Discover the vibrant atmosphere of Walk on White in Key West's The Meadows neighborhood. This event invites you to enjoy the lively rhythms of talented…
Bria Ansara at Berlin’s Cocktail Bar
At Berlin's Cocktail Bar, immerse yourself in the enchanting melodies of Bria Ansara. Her captivating jazz performance complements the bar's timeless charm, creating an unforgettable…
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
Join the excitement at Brady's Pub in Key West for Catch The Mania Trivia. Hosted by a dynamic and entertaining quizmaster, this lively event promises…
Free
Andy’s Cabana Open Mic No Mic Night
Andy's Cabana in Key West's Bahama Village transforms into a lively stage during the Open Mic No Mic Night, where talented entertainers captivate the audience…
Free
Karaoke with Foss at RockHouse Live
Join Foss for an unforgettable karaoke night at RockHouse Live, Key West. Known for his electrifying presence and talent, Foss elevates the evening with engaging…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant nightlife at Bobby's Monkey Bar in Old Town Key West, where the standout entertainer takes the stage for an unforgettable karaoke experience.…
Riptide Riot at Irish Kevin’s Bar
Riptide Riot, a dynamic power duo hailing from Key West, electrifies audiences at Irish Kevin's Bar. Featuring Jim Simonian on drums and vocals and Tim…
Free