Wednesday Filet Day at Mary Ellen’s
Every Wednesday at Mary Ellen's Bar in Old Town Key West, enjoy Filet Day alongside live entertainment that electrifies the neighborhood atmosphere. While savoring comfort…
Free
53 events found.
Events for March 26, 2026
Ongoing
DJ Duke ~ Rick’s Bar Upstairs Stage
Experience an unforgettable night as DJ Duke takes over the Upstairs Stage at Rick's Bar. Known for his dynamic and innovative style, DJ Duke captivates…
Free
Crank Sinatra~ Durty Harry’s Stage
Crank Sinatra~ Durty Harry's Stage features the talented musician Spogga, who captivates the audience with his dynamic performances. At Rick's Entertainment Complex in vibrant Key…
Free
Kc Johns Band at Hog’s Breath Saloon
Experience the dynamic KC Johns Band at Hog's Breath Saloon, where powerhouse vocalist KC Johns delivers a captivating blend of country and rock. With roots…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant scene at Bobby's Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high,…
Karaoke w/ Davis ~ Rick’s Bar Downstairs Stage
Join DJ Davis for an unforgettable karaoke night at Rick's Bar Downstairs Stage in Key West. Known for his vibrant energy and engaging style, DJ…
Free
Ambitious Morning Runners
Join the Ambitious Morning Runners at White Street Pier in Key West for an invigorating start to your day. While there isn't a specific entertainer,…
Free
Fishmonster Max- Daily Party Boat Fishing
Fishmonster Max offers a thrilling daily party boat fishing experience in Key West, perfect for families and groups. With its stable twin hulls, the boat…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Join a unique yoga experience with renowned instructors at Yoga on the Beach at Fort Zachary Taylor. Set against the backdrop of Key West’s historic…
$20
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga, a rejuvenating experience amidst the serene beauty of the Key West Tropical Forest & Botanical Garden. Known…
$20
Izzy Zaidman at Sloppy Joe’s Bar
Izzy Zaidman brings the soulful sounds of American Roots to Sloppy Joe's Bar in Key West, where his Steel Resonator guitar captivates audiences. Since moving…
Free
Trenton Chandler ~ Rick’s DownStairs Stage
Trenton Chandler, hailing from Shallowater, Texas, is a charismatic country musician known for his heartfelt songwriting and engaging live performances. Drawing inspiration from legends like…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
There is a minimum of 4 people. Please contact mojitoclass@gmail.com to schedule. Please put how many people and date in the subject line. Join Key…
$75.00
Distillery Tour – Key West Legal Rum Distillery
Experience an engaging distillery tour at Key West Legal Rum Distillery, featuring a skillful entertainer who brings the history and craft of rum making to…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the captivating Glass Bottom Boat tour in Key West, where our knowledgeable captain and crew offer an engaging eco-tour. Enjoy unparalleled views of North…
$69.95
Dan Harvey at Hog’s Breath Saloon
Dan Harvey captivates audiences with his dynamic performances at Hog's Breath Saloon in Key West's Mallory Square District. Known for his engaging stage presence and…
Free
Sid The Bayou Kid at Sloppy Joe’s Bar
Experience the charismatic performance of Sid The Bayou Kid at Sloppy Joe's Bar. Originating from Thibodaux, Louisiana's swamps, Sid captivates audiences nationwide with his unique…
Free
Ross Brown at Schooner Wharf Bar
Ross Brown captivates audiences at Schooner Wharf Bar with his electrifying performances. As a talented musician, he perfectly complements the bar's laid-back island atmosphere with…
Free
Ross Brown at Schooner Wharf Bar
Ross Brown captivates audiences at Schooner Wharf Bar with his electrifying performances. As a talented musician, he perfectly complements the bar's laid-back island atmosphere with…
Free
Truman Waterfront Farmers Market
Enjoy the vibrant atmosphere at Truman Waterfront Farmers Market, where local entertainers set the mood with captivating performances. Every Thursday from 2 to 7 pm,…
Free
Truman Waterfront Farmers Market
Enjoy the vibrant atmosphere at Truman Waterfront Farmers Market, where local entertainers set the mood with captivating performances. Every Thursday from 2 to 7 pm,…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the magic of Key West's marine life aboard the Glass Bottom Boat. While our knowledgeable captain and crew guide you on an informative eco-tour,…
$69.95
Just George at The Alamo Key West
Experience the captivating performance of Just George at The Alamo Key West, a lively bar and grill in Old Town. As you indulge in mouthwatering…
Free
Just George at The Alamo Key West
Experience the captivating performance of Just George at The Alamo Key West, a lively bar and grill in Old Town. As you indulge in mouthwatering…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join us for a vibrant aquatic adventure in Key West with our Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise. Our passionate and friendly…
$79.95
Jeff Harris ~ Rick’s Bar Downstairs Stage
Experience the captivating talent of musician Jeff Harris at Rick's Bar Downstairs Stage. Known for his engaging performances, Jeff brings an array of musical styles…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience an unforgettable journey with Glass Bottom Boat - Key West's Window to the Sea. With an engaging and knowledgeable captain and crew, embark on…
$69.95
Alex Anthony Duo at Hog’s Breath Saloon
Experience the electrifying performance of the Alex Anthony Duo at Hog's Breath Saloon. Known for their modern take on the cover band scene, Alex Anthony…
Free
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls captivate audiences with their dazzling performances at the lively 801 Bourbon Bar in Old Town Key West. Known for their…
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
Free
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Enjoy an unforgettable night at Sloppy Joe's Bar with Pete & Larry, known as Sloppy 2nds. This dynamic duo brings infectious energy, delivering belly-aching laughs…
Free
Filming Sit with Kit Podcast Episodes
Join charismatic host Kit in filming Sit with Kit podcast episodes at Angelina's Pizzeria in Key West. Known for its vibrant energy and engaging conversations,…
Free
Bria Ansara at Berlin’s Cocktail Bar
Immerse yourself in an unforgettable evening with Bria Ansara at Berlin's Cocktail Bar. Nestled in Key West's A&B Lobster House, this hidden gem offers a…
Free
Nick Brownell at Schooner Wharf Bar
Nick Brownell brings his musical talents to the laid-back atmosphere of Schooner Wharf Bar in Key West. As a musician, he captivates audiences with his…
Free
Shine & Friends at The Alamo Key West
Experience an unforgettable evening with Shine at The Alamo Key West. Known for mesmerizing performances, Shine captivates audiences with a unique blend of music, creating…
Free
Nick Brownell at Schooner Wharf Bar
Nick Brownell brings his musical talents to the laid-back atmosphere of Schooner Wharf Bar in Key West. As a musician, he captivates audiences with his…
Free
Shine & Friends at The Alamo Key West
Experience an unforgettable evening with Shine at The Alamo Key West. Known for mesmerizing performances, Shine captivates audiences with a unique blend of music, creating…
Free
Catch The Mania Trivia at Brady’s Pub
Join us at Brady's Pub for Catch The Mania Trivia, hosted by an enigmatic entertainer who promises a night of fun and excitement. Dive into…
Free
Andy’s Cabana Open Mic No Mic Night
At Andy's Cabana Open Mic No Mic Night, the real star is the performer who captivates the audience with raw, acoustic talent. In the heart…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting world of Frank Everhart at Schooner Wharf Bar. Known for his masterful sleight of hand and captivating storytelling, Everhart takes you on…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting world of Frank Everhart at Schooner Wharf Bar. Known for his masterful sleight of hand and captivating storytelling, Everhart takes you on…
Free
Joe the Show ~ Rick’s Bar Downstairs Stage
Experience the electrifying talent of Joe The Show, a dynamic musician revered for his captivating performances at Rick's Bar Downstairs Stage. Known for his energetic…
Free
iWitness Crime Tour – Meeting Place
Join the iWITNESS True Crime Walking Tour and embark on a thrilling journey through Key West's most notorious crime scenes. Led by an engaging expert…
$45.00
iWITNESS True Crime Walking Tour
Join the iWITNESS True Crime Walking Tour and embark on a thrilling journey through Key West's most notorious crime scenes. Led by an engaging expert…
$45.00
DJ Chaka ~ Rick’s Bar Upstairs Stage
Experience an electrifying night with DJ Chaka at Rick's Bar Upstairs Stage in Key West. Known for his dynamic beats and infectious energy, DJ Chaka…
Free
The Durtbags ~ Durty Harry’s Stage
Experience the electrifying performance of The Durtbags at Durty Harry's Stage, located within Rick's Entertainment Complex in Key West. This dynamic rock band lights up…
Free
Kc Johns Band at Hog’s Breath Saloon
Experience the electrifying KC Johns Band at Hog's Breath Saloon, where powerhouse vocalist KC Johns delivers an irresistible fusion of country and rock. With her…
Free
Karaoke with Foss at RockHouse Live
Experience an unforgettable night of entertainment with Foss at RockHouse Live in Key West. Known for electrifying performances, Foss brings charisma and energy to the…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant scene at Bobby's Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high,…
The Audio Files at Sloppy Joe’s Bar
Experience the electrifying energy of The Audio Files at Sloppy Joe's Bar, where this ultimate party rock band delivers Top 40 pop and rock hits…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join DJ Jason at Rick's Bar Downstairs Stage for an exhilarating night of karaoke. Known for his electrifying mixes and innovative soundscapes, Jason blends genres…
Free