DJ Marty at Red Garter Saloon Stage
Experience the electrifying energy of DJ Marty at the Red Garter Saloon Stage in Key West's Rick's Entertainment Complex. Renowned for his seamless mixing and…
Free
58 events found.
Events for April 20, 2026
Ongoing
Homegrown at Hog’s Breath Saloon
Homegrown is a dynamic country band from Key West, celebrated for their heartfelt lyrics and captivating melodies. Performing at Hog's Breath Saloon, they offer a…
Free
Karaoke at Bobby’s Monkey Bar
Experience an unforgettable evening at Bobby's Monkey Bar with dynamic karaoke sessions led by an engaging and talented entertainer. Nestled in Key West's Old Town,…
Mylo O’Maolain at Irish Kevin’s Bar
Experience the charismatic Mylo O'Maolain captivating audiences at Irish Kevin's Bar in Key West. Known for his vibrant performances, Mylo brings infectious energy and musical…
Free
Radio Hero at Sloppy Joe’s Bar
Experience the electrifying energy of Radio Hero at Sloppy Joe's Bar, where this edgy party rock band delivers high-octane performances that captivate audiences. Known for…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max daily party boat fishing excursion at A & B Marina in Key West's historic seaport. While the details of the entertainer…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Enjoy a serene yoga session at Fort Zachary Taylor State Park's stunning beach location. While an emphasis on the entertainer is absent, the park itself…
$20
Aqua Yoga at Southernmost Beach Resort
Join us at Southernmost Beach Resort for a unique Aqua Yoga experience. This tranquil oasis offers the perfect blend of modern luxury and tradition with…
$20
Lance Taylor at Two Friends Patio Restaurant
Lance Taylor takes the stage at Two Friends Patio Restaurant, bringing his vibrant musical talents to this beloved Key West venue. Known for his captivating…
Free
Rolando Rojas at Sloppy Joe’s Bar
Experience the captivating performance of Rolando Rojas at Sloppy Joe's Bar, where his electrifying presence and unique style energize the iconic Key West venue. Renowned…
Free
Nick Norman at Rams Head Southernmost
Nick Norman, a talented singer-songwriter from South Carolina, enchants audiences with his soulful vocals and poignant songwriting. Now a Key West resident, he effortlessly blends…
Free
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck brings vibrant energy to Irish Kevin's Bar in Old Town Key West. With live performances that captivate audiences, he elevates the pub's lively…
Free
Distillery Tour – Key West Legal Rum Distillery
Explore the Key West First Legal Rum Distillery, nestled in the Historic Seaport. Delight in daily tours and rum samples while embracing vibrant nightlife vibes.…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West First Legal Rum Distillery, where a charismatic entertainer will guide you through a lively mojito-making experience. Delight in…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West for an unforgettable journey beneath the sea. While soaking in vibrant marine life through crystal-clear waters,…
$69.95
Webb Dillard at Rick’s Bar Downstairs Stage
Experience the enchanting performance of Webb Dillard at Rick's Bar Downstairs Stage. Known for his work with TikiBar Nation, Dillard transforms live entertainment into a…
Free
Zack Seemiller at Hog’s Breath Saloon
Zack Seemiller captivates audiences at Hog's Breath Saloon with his dynamic performances, combining his talents as a musician and songwriter. Known for engaging and inspiring…
Free
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan brings his musical talents to Sloppy Joe's Bar, creating an unforgettable live music experience in Key West. Known for his dynamic performances, Tim…
Free
Jay Klein at Schooner Wharf Bar
Jay Klein, an innovative musician and dynamic performer, brings his unique style to the lively Schooner Wharf Bar in Key West. As a multifaceted artist,…
Free
Rick Fusco at Two Friends Patio Restaurant
Enjoy the captivating performance of musician Rick Fusco at Two Friends Patio Restaurant in Key West. With his engaging style and musical talent, Rick enhances…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
The Glass Bottom Boat Cruise in Key West offers a unique marine adventure, enhanced by a captivating entertainer who brings the vibrant sea life into…
$69.95
Jon Hollywood at Tiki House Key West
Experience the enigmatic charm of Jon Hollywood at Tiki House Key West, where his charismatic presence and captivating storytelling take center stage. Known for blending…
Free
Jeff Harris at Irish Kevin’s Bar
Jeff Harris is a dynamic entertainer performing at Irish Kevin's Bar in Key West. Known for his talent as a singer, songwriter, and comedian, Jeff…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience an unforgettable adventure with Sunset Watersports' Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise in Key West. Guided by knowledgeable and engaging staff,…
$79.95
Just George at Rick’s Bar Downstairs Stage
Experience the soulful melodies of Just George at Rick's Bar Downstairs Stage. A dedicated musician from Key West, Just George delivers heartfelt acoustic performances that…
Free
Cliff Cody at Mac’s Place
Enjoy an evening with Cliff Cody at Mac's Place, a talented indie country singer-songwriter hailing from Texas and now based in Key West. Known for…
Free
Monday Night Commander
Join us at Monday Night Commander for an exciting evening of Commander gameplay and thrilling competitions. Enjoy the chance to win free promos and prize…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West for an unforgettable maritime adventure. While the vibrant marine life and crystal-clear waters captivate, it's…
$69.95
Puff Puff… Float! A 4/20 Bud Crawl
Join us for Puff Puff... Float! A 4/20 Bud Crawl featuring a lively mobile DJ who will set the rhythm for our high-vibe celebration. With…
Free
Ross Brown Duo at Hog’s Breath Saloon
Experience the captivating performance of the Ross Brown Duo at Hog's Breath Saloon. Ross Brown, a versatile musician from Key West, infuses his love for…
Free
World Famous 801 Girls- 5pm Show
Experience the captivating performances of the World Famous 801 Girls during their 5pm matinee show at 801 Bourbon Bar in Key West. Known for their…
Monday, April 20 SRC Meeting 🇺🇸
Join the Monday, April 20 SRC Meeting at American Legion Post 28, where all registered Republicans are welcome. This event emphasizes local action for impactful…
Free
Glow Hours on Hugh’s View
Join Glow Hours on Hugh's View at The Studios of Key West for a captivating evening featuring remarkable live performances. Set in a beautifully renovated…
Tony Roberts at Rams Head Southernmost
Tony Roberts, a versatile American actor renowned for his film, television, and theater contributions, graces Rams Head Southernmost. Known for his roles in Woody Allen…
Free
CONCH REPUBLIC MILITARY MUSTER
The Conch Republic Military Muster celebrates its annual Independence at the Key West Cultural Center and Veterans Museum. After the Muster, attendees can enjoy an…
Free
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square, where the highlight is the captivating performances by street entertainers. With acts ranging from jugglers to the…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant rhythms of Caribe of Key West at El Meson de Pepes on Mallory Square. Caribe captivates audiences with lively performances that perfectly…
CW Colt at Two Friends Patio Restaurant
Experience the captivating performances of musician CW Colt at Two Friends Patio Restaurant in Key West. Known for his engaging stage presence and soulful tunes,…
Free
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Experience the dynamic talents of Pete & Larry Sloppy 2nds at Sloppy Joe's Bar, Key West. Known for their eclectic style and spontaneous energy, this…
Free
Barrett Thomas at The Alamo Key West
Experience the captivating sounds of Barrett Thomas, a talented live musician and looper based in Key West. Known for his innovative performances, Barrett expertly layers…
Free
NY Pauly at Irish Kevin’s Bar
NY Pauly, a legendary performer at Irish Kevin's Bar in Key West, Florida, captivates audiences with his extraordinary blend of music and entertainment. His vibrant…
Free
Martini Monday at Virgilios
Martini Monday at Virgilios in Old Town Key West offers an enchanting evening filled with live music that captivates the audience. As you savor premier…
Free
Charity Bingo at The Green Parrot
Join us for Charity Bingo at The Green Parrot in Key West, an iconic dive bar with a vibrant atmosphere. Discover captivating entertainment that elevates…
Free
Movie Night at The Retro Room
Join us at The Retro Room in Old Town Key West for an unforgettable Movie Night. With a lively atmosphere featuring 24 taps of cold…
Free
Lary Smith Jazz Jam at William Weech American Legion Post 168
Larry Smith, a renowned musician, leads a captivating Jazz Jam at the William Weech American Legion Post 168 in Key West. Known for his soulful…
Free
Charles Miller at Rick’s Bar Downstairs Stage
Experience the captivating performance of Charlie Miller at Rick's Bar Downstairs Stage. A dynamic musician and spirited sailor, Charlie embodies a modern-day pirate and gypsy,…
Free
Joe The Show at Schooner Wharf Bar
Experience the electrifying Joe The Show at Schooner Wharf Bar, where his dynamic energy and exceptional talent light up the vibrant Key West music scene.…
Free
DJ Marty at Red Garter Saloon Stage
Experience the electrifying beats of DJ Marty at the Red Garter Saloon Stage in Key West. Known for his innovative mixing and dynamic performances, DJ…
Free
Elle Haley at Halo Rooftop Lounge Bar at The Saint
Experience the enchanting musical talent of Elle Haley at the Halo Rooftop Lounge Bar at The Saint Hotel. Known for her vibrant and soulful performances,…
Free
Gregory James at La Te Da
Experience the dynamic talent of Gregory James at La Te Da in Key West. A versatile entertainer, Gregory is skilled in acting, modeling, and performing…
Free
Jefff Clark at Tiki House Key West
Experience the vibrant soundscapes of Jefff Clark at Tiki House Key West. A rising star in the music industry, Jefff captivates audiences with his innovative…
Free
DJ Duke at Rick’s Bar Upstairs Stage
Experience the electrifying energy of DJ Duke at Rick's Bar Upstairs Stage. Renowned for his mesmerizing mixes and vibrant stage presence, DJ Duke captivates audiences…
Free
HYPER DRIVE at Durty Harry’s Stage
Experience the electrifying performance of Hyper Drive at Durty Harry's Stage. This dynamic entertainer, known for his captivating vocals and guitar prowess, delivers powerful melodies…
Free
DRUNKEN SPELLING BEE
Experience a night of laughter and linguistic challenges at the Drunken Spelling Bee hosted by Comedy Key West at Mary Ellen’s Bar. Known for its…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience the electrifying energy of the Alex Anthony Band at Hog's Breath Saloon in Key West. Renowned for reinventing the modern cover band experience, Alex…
Free
Karaoke at Bobby’s Monkey Bar
Experience a vibrant night at Bobby's Monkey Bar in Key West's Old Town, featuring karaoke nightly in a lively island atmosphere. Though the entertainer details…
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O’Maolain captivates audiences at Irish Kevin's Bar with his dynamic performances and engaging charisma. Known for his lively music and infectious energy, Mylo creates…
Free
Radio Hero at Sloppy Joe’s Bar
Experience the electrifying energy of Radio Hero at Sloppy Joe's Bar. Known for their explosive party rock performances, Radio Hero captivates audiences with their dynamic…
Free