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…
61 events found.
Events for February 19, 2026
Ongoing
Pierce August at Hog’s Breath Saloon
Pierce August captivates audiences at Hog's Breath Saloon with his dynamic performances and engaging stage presence. Known for his eclectic mix of genres, Pierce's music…
Free
Dan Harvey Duo at Hog’s Breath Saloon
Experience the vibrant sounds of the Dan Harvey Duo at Hog's Breath Saloon in Key West. Renowned for their captivating performances, the duo brings a…
Free
DJ Todd ~ Red Garter Saloon Stage
DJ Todd electrifies the Red Garter Saloon Stage at Rick's Entertainment Complex with an unforgettable mix of beats and rhythms. As the heart of Key…
Free
DJ Duke ~ Rick’s Bar Upstairs Stage
Experience the electrifying sounds of DJ Duke at Rick's Bar Upstairs Stage, where his vibrant beats set the perfect mood for an unforgettable night. Known…
Free
Marshall Morlock Band at General Horseplay
Experience the electrifying performances of the Marshall Morlock Band at General Horseplay, an iconic venue on Duval Street in Old Town Key West. Known for…
Free
CRANK SINATRA~ Durty Harry’s Stage
Join Krank Sinatra on Durty Harry's Stage at Rick's Entertainment Complex in Key West's vibrant Old Town. Known for their electrifying performances, Krank Sinatra delivers…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience the electrifying Alex Anthony Band live at Hog's Breath Saloon, where Alex's dynamic performance lights up Key West's favorite dive bar. Known for their…
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,…
Kari Wolf at Irish Kevin’s Bar
Experience the electrifying performance of Kari Wolf at Irish Kevin’s Bar in Key West. Known for her dynamic stage presence and musical talent, Kari captivates…
Free
Karaoke w/ Davis ~ Rick’s Bar Downstairs Stage
Join Davis for an unforgettable night of karaoke at Rick's Bar Downstairs Stage in Old Town Key West. Known for his dynamic energy and engaging…
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
Join Fishmonster Max for an unforgettable daily party boat fishing adventure in Key West, where entertainment meets the thrill of fishing. Whether it's a family…
$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
Victoria Leigh at Sloppy Joe’s Bar
Victoria Leigh, a dynamic Florida Keys singer, guitarist, and loop artist, electrifies audiences at Sloppy Joe's Bar. Known for her energetic performances and creative mashups,…
Free
Mylo O’Maolain at Irish Kevin’s Bar
Catch Mylo O'Maolain live at Irish Kevin's Bar in Key West's vibrant Old Town. Experience his dynamic musical performances, engaging the crowd with every note.…
Free
Trenton Chandler ~ Rick’s DownStairs Stage
Catch the electrifying performance of Trenton Chandler at Rick's DownStairs Stage in Key West. A talented country musician from Shallowater, Texas, Trenton draws inspiration from…
Free
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
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
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
Sid The Bayou Kid at Sloppy Joe’s Bar
Sid The Bayou Kid, a charismatic musician from Thibodaux, LA, captivates audiences with his swamp-infused sound. With over 30 years of experience, Sid brings his…
Free
Ross Brown at Schooner Wharf Bar
Experience the captivating sounds of Ross Brown at Schooner Wharf Bar, Key West. This talented musician brings vibrant energy to the historic, open-air setting, enhancing…
Free
Barrett Thomas at Hog’s Breath Saloon
Experience the dynamic performance of musician Barrett Thomas at Hog's Breath Saloon, where his captivating tunes energize the venue's lively atmosphere. Nestled in Key West's…
Free
Marjory Lee at Sunset Pier
Experience the captivating sounds of musician Marjory Lee at Sunset Pier, where her enchanting performances complement the vibrant ambiance of Key West's waterfront. Nestled where…
Free
Tony Baltimore at Hank’s Hair of the Dog Saloon
Tony Baltimore brings his captivating musical talent to Hank's Hair of the Dog Saloon in Key West. Known for his dynamic performances, Tony enchants audiences…
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
Jon Hollywood at Tiki House Key West
Join the charismatic Jon Hollywood at Tiki House Key West for an unforgettable evening of entertainment. Known for his captivating performances and energetic stage presence,…
Free
David Warren at The Bull & Whistle Bar
Experience the captivating performance of David Warren at The Bull & Whistle Bar in Key West. Known for his dynamic stage presence and soulful tunes,…
Free
Irish Kevin at Irish Kevin’s Bar
Experience the charismatic performances of Irish Kevin at Irish Kevin’s Bar in Key West's Old Town. Known for his engaging live music and dynamic crowd…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join an exhilarating aquatic adventure with the Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise. Led by our passionate and expert staff, enjoy thrilling…
$79.95
Jeff Harris ~ Rick’s Bar Downstairs Stage
Experience the captivating talent of musician Jeff Harris at Rick's Bar Downstairs Stage. Located in vibrant Old Town Key West, this venue is part of…
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
Dan Harvey Duo at Hog’s Breath Saloon
Experience the vibrant sounds of the Dan Harvey Duo at Hog's Breath Saloon. Known for their captivating performances, this talented musical duo creates an unforgettable…
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…
Elle Haley at Hank’s Hair of the Dog Saloon
Elle Haley captivates audiences at Hank's Hair of the Dog Saloon with her mesmerizing musical performances. Known for her dynamic vocals and engaging stage presence,…
Free
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…
Reggae Lou and The Kind Buda at Sunset Pier
Experience the captivating rhythms of Reggae Lou and The Kind Budz at Sunset Pier, Key West. This dynamic band infuses the air with reggae vibes,…
Free
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Catch the dynamic duo Pete & Larry, better known as Sloppy 2nds, at the iconic Sloppy Joe's Bar. With their infectious humor and lively performances,…
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 iconic Schooner Wharf Bar, a beloved Key West venue known for its relaxed atmosphere and stunning dockside…
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
Joe the Show ~ Rick’s Bar Downstairs Stage
Experience the electrifying performance of Joe the Show at Rick's Bar Downstairs Stage in the heart of Key West. This dynamic musician captivates audiences with…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar in Key West's Seaport. A master magician, Everhart captivates audiences with mesmerizing illusions and…
Free
DJ Marty ~ Red Garter Saloon Stage
Experience the electrifying beats of DJ Marty on the Red Garter Saloon Stage at Rick's Entertainment Complex in Key West. Known for his high-energy sets,…
Free
Hot Girl Bummer at General Horseplay
Join the excitement at General Horseplay with Hot Girl Bummer, an electrifying entertainer known for her dynamic performances and infectious energy. Located in vibrant Old…
Free
Marty Stuart And His Fabulous Superlatives at Key West Theater
Experience the legendary Marty Stuart and His Fabulous Superlatives as they bring their electrifying performance to the historic Key West Theater. Known for his mastery…
$
Sandra Lee at The Bull & Whistle Bar
Sandra Lee captivates audiences at The Bull & Whistle Bar in Key West with her electrifying performances. Known for her dynamic musical talent, Sandra brings…
Free
DJ Chaka ~ Rick’s Bar Upstairs Stage
Experience an electrifying night with DJ Chaka on the Rick's Bar Upstairs Stage. Known for spinning an eclectic mix of tunes that keep the crowd…
Free
The Tiki Bombs at Tiki House Key West
Experience an unforgettable night with The Tiki Bombs at the Tiki House Key West. This electrifying band brings a vibrant, energetic performance, delivering explosive sounds…
Free
DURTBAGS~ Durty Harry’s Stage
Experience the electrifying energy of The Durtbags, Key West’s premier party rock band, at Durty Harry's Stage. Every Thursday through Sunday, they deliver unforgettable live…
Free
Barrett Thomas at Hank’s Hair of the Dog Saloon
Experience the captivating sounds of Barrett Thomas at Hank's Hair of the Dog Saloon in Key West. Known for his engaging performances, Barrett brings lively…
Free
Elle Haley and the Why Nots at General Horseplay
Elle Haley and the Why Nots captivate audiences at General Horseplay with their eclectic sound and magnetic stage presence. Known for their lively performances, this…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience the electrifying Alex Anthony Band live at Hog's Breath Saloon, Key West. Known for their dynamic performances and captivating energy, Alex Anthony leads a…
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,…
Naked Karate Girls at Sloppy Joe’s Bar
The Naked Karate Girls, hailed as the best band in the galaxy, bring their high-energy performance to Sloppy Joe's Bar from 10:00 pm to 2:00…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable karaoke experience at Rick's Bar on the Downstairs Stage. Known for his engaging presence and charismatic hosting style, Jason turns…
Free