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
55 events found.
Events for February 20, 2026
Ongoing
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
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
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
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
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,…
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
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
Rolando Rojas at Sloppy Joe’s Bar
Experience the electrifying performance of Rolando Rojas at Sloppy Joe's Bar, where his charismatic stage presence and exceptional guitar skills captivate audiences. As a leading…
Free
Story Time at the Key West Library
Join us every Tuesday at the Key West Library for an enchanting Storytime in the Garden with a captivating storyteller who brings tales to life.…
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
Mike Stack & D-Lew at Tiki House Key West
Experience an unforgettable night at Tiki House Key West with the dynamic duo, Mike Stack & D-Lew. Their electrifying performance blends captivating melodies and energizing…
Free
Wynn Tayor ~ Rick’s Bar Downstairs Stage
Catch the captivating Wynn Taylor performing live at Rick's Bar Downstairs Stage. Known for his energetic and soulful performances, Wynn brings a dynamic blend of…
Free
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan, a talented musician originally from Columbia, South Carolina, captivates audiences at Sloppy Joe's Bar in Key West. Known for his engaging stage presence,…
Free
Tony Baltimore at Schooner Wharf Bar
Tony Baltimore brings his vibrant musical talent to the Schooner Wharf Bar, infusing the historic Key West venue with captivating live performances. In a laid-back,…
Free
Elle Haley at Hog’s Breath Saloon
Experience the captivating performance of musician Elle Haley at Hog's Breath Saloon, a vibrant venue in Key West's Mallory Square District. Elle fills the dive…
Free
Jockey Jord at Sunset Pier
Experience an unforgettable evening with Jockey Jord at Sunset Pier. This talented musician captivates audiences with lively tunes against the stunning backdrop of Key West's…
Free
Pat Guadano and Friends at Hank’s Hair of the Dog Saloon
Pat Guadano and Friends bring an electrifying performance to Hank's Hair of the Dog Saloon in Key West. Known for his soulful voice and masterful…
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
Jessie Cotton Stone at The Bull & Whistle Bar
Experience the captivating sounds of Jessie Cotton Stone at The Bull & Whistle Bar, a vibrant venue in Key West's Old Town. Known for engaging…
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
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
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
Joe the Show ~ Rick’s Bar Downstairs Stage
Experience an electrifying performance by Joe the Show at Rick's Bar Downstairs Stage. Known for his dynamic presence and musical prowess, Joe captivates audiences with…
Free
Dan Harvey Duo at Hog’s Breath Saloon
Experience the electrifying performance of the Dan Harvey Duo at Hog's Breath Saloon in Key West. Known for their captivating tunes and vibrant energy, the…
Free
Rochi and Prince at Hank’s Hair of the Dog Saloon
Experience the captivating performance of Rochi and Prince at Hank's Hair of the Dog Saloon in Key West. Known for their dynamic stage presence and…
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
Snacks and Five at Sunset Pier
Snacks and Five captivate audiences at Sunset Pier with vibrant live performances set against the stunning Key West sunset. Nestled where Duval Street meets the…
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
JOE THE SHOW ~ Durty Harry’s Stage
Experience the electrifying performance of Joe The Show at Durty Harry's Stage in Key West's iconic Rick's Entertainment Complex. Known for his dynamic musical talent…
Free
Scallywagz Band at Schooner Wharf Bar
Experience the vibrant sounds of the Scallywagz Band at the Schooner Wharf Bar in Key West. Known for their lively performances, the band brings an…
Free
Gerd Rube at Tiki House Key West
Experience the captivating sounds of Gerd Rube at Tiki House Key West. Renowned for his dynamic performances and eclectic music style, Gerd Rube brings a…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at the Schooner Wharf Bar in Key West. Known for captivating performances, Everhart's illusions and sleight-of-hand tricks mesmerize…
Free
DJ Marty ~ Red Garter Saloon Stage
Experience the electrifying vibes of DJ Marty at the Red Garter Saloon Stage in Rick's Entertainment Complex. Known for his dynamic mixes and infectious energy,…
Free
The Original Key West Pub Crawl
Join The Original Key West Pub Crawl for a lively 2.5-hour adventure spotlighted by entertaining guides who infuse humor and energy into the experience. Enjoy…
$39.95
Elle Haley ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Elle Haley on the Downstairs Stage at Rick's Bar. Known for her dynamic presence and soulful sound, Elle creates…
Free
DJ Duke ~ Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Duke at Rick's Bar Upstairs Stage. Known for his dynamic sets and unparalleled energy, DJ Duke transforms the vibrant…
Free
Karaoke at Two Friends Patio
Experience unforgettable evenings at Two Friends Patio with lively karaoke sessions hosted by charismatic entertainers. Sing your heart out on the open-air patio, soaking in…
Free
Bone Island Haunted Pub Crawl & Ghost Tour
Join the Bone Island Haunted Pub Crawl & Ghost Tour for an enthralling evening led by a charismatic entertainer. With captivating narration, journey through America's…
$29.95
Victoria Leigh at Hank’s Hair of the Dog Saloon
Victoria Leigh captivates audiences with her electrifying performances at Hank's Hair of the Dog Saloon. This talented musician brings her dynamic sound to Key West’s…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience the vibrant sounds of the Alex Anthony Band at Hog's Breath Saloon. Known for electrifying performances, Alex Anthony captivates audiences with a unique blend…
Free
David Warren Band at The Bull & Whistle Bar
Experience the electrifying performance of the David Warren Band at The Bull & Whistle Bar in Key West. Renowned for their dynamic stage presence and…
Free
DURTBAGS ~ Durty Harry’s Stage
Catch Key West's ultimate party experience with The Durtbags at Durty Harry's Stage! This electrifying rock band performs live every Thursday through Sunday at Rick’s…
Free
Tequila Time Machine at General Horseplay
Experience the electrifying energy of Tequila Time Machine at General Horseplay, where this captivating band transports you through musical eras with their dynamic performances. Nestled…
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
Experience the electrifying energy of the Naked Karate Girls, the ultimate party band hailing from Cincinnati. Known as The Best Band in the Galaxy, their…
Free
Trumastr at Tiki House Key West
Experience the captivating performance of Trumastr at Tiki House Key West! Known for his dynamic presence and exceptional musical talent, Trumastr creates an unforgettable atmosphere…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable karaoke night at Rick's Bar Downstairs Stage. Known for his infectious energy and captivating charisma, Jason transforms the evening into…
Free