HaveFun.NOW

Rolando Rojas at Sloppy Joe's Bar
2026-02-13 10:00 - 11:45 (America/New_York)
Renowned for his charismatic stage presence and exceptional guitar skills, Rolando Rojas electrifies audiences at Sloppy Joe’s Bar. A Key West wedding favorite, his performances blend talent and energy seamlessly. At the historic bar, guests enjoy lively tunes, capturing the vibrant essence of Old Town Key West in an unforgettable musical experience.

Story Time at the Key West Library
2026-02-13 11:00 - 12:00
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. Held in the picturesque Key West Tropical Forest & Botanical Garden, this free event invites young minds to explore nature and imagination through engaging stories, crafts, and activities.

Jeff Harris at Irish Kevin’s Bar
2026-02-13 11:00 - 14:30
Experience the electrifying performances of Jeff Harris at Irish Kevin’s Bar, where his captivating live music brings the crowd to life. Situated in Key West’s vibrant Old Town, this energetic venue ensures unforgettable nights with nonstop entertainment and audience participation, all while enjoying craft beers and hearty pub fare. Don’t miss Jeff Harris’s unforgettable show!

Wynn Tayor ~ Rick's Bar Downstairs Stage
2026-02-13 12:00 - 16:00
Experience the captivating performance of musician Wynn Taylor at Rick’s Bar Downstairs Stage in Key West’s iconic Rick’s Entertainment Complex. Known for his engaging and soulful melodies, Wynn captivates the audience with every note. Dive into an unforgettable night of live music and vibrant nightlife at Key West’s largest entertainment venue.

Tim Hollohan at Sloppy Joe's Bar
2026-02-13 12:00 - 16:45
Experience the vibrant energy of Tim Hollohan at Sloppy Joe’s Bar, Key West. Originally from Columbia, South Carolina, Tim graces this iconic venue with captivating performances nearly every day. His dynamic presence and engaging interaction with the audience create unforgettable musical experiences in this historic landmark of live entertainment.

Tony Baltimore at Schooner Wharf Bar
2026-02-13 12:00 - 17:00
Experience the captivating rhythms of Tony Baltimore at the Schooner Wharf Bar in Key West. Known for his dynamic performances, Tony enchants audiences with his musical prowess in this laid-back, open-air venue. Enjoy the vibrant atmosphere, live tunes, and stunning dockside views, making for an unforgettable night of entertainment by the sea.

Elle Haley at Hog's Breath Saloon
2026-02-13 12:00 - 2026-02-14 16:00
Experience a captivating evening with Elle Haley at Hog’s Breath Saloon in Key West’s vibrant Mallory Square District. Known for her mesmerizing performances, Elle brings an energizing mix of music that complements the lively atmosphere. Enjoy her enchanting melodies while savoring pub delights on the covered patio of this iconic dive bar.

Sheldon Benton at Sunset Pier
2026-02-13 13:00 - 16:00
Join us at Sunset Pier for an unforgettable evening with Sheldon Benton, a captivating performer known for his soulful melodies and engaging stage presence. Set against the stunning Key West sunset, enjoy an experience filled with vibrant entertainment and refreshing tropical drinks. Perfect for music lovers and sunset chasers alike.

Jessie Cotton Stone at The Bull & Whistle Bar
2026-02-13 14:00 - 18:00
Experience the electrifying performance of Jessie Cotton Stone at The Bull & Whistle Bar in Key West. Known for his soulful melodies and dynamic stage presence, Jessie captivates audiences in this lively, open-air venue. Surrounded by murals and vibrant crowds, enjoy potent cocktails and an unforgettable night of live music on Duval Street.

Mylo O'Maolain at Irish Kevin’s Bar
2026-02-13 14:30 - 18:30
Mylo O’Maolain is a captivating musician performing at Irish Kevin’s Bar. Known for his engaging live shows and infectious energy, Mylo expertly blends traditional tunes with modern flair, inviting audience participation. His performances transform the lively Key West venue into a spirited celebration, making every night unforgettable with harmonious melodies and vibrant entertainment.

Daytime event to test 38, Stage C
2026-02-13 16:00 - 18:00 | test venue 7, 416 Applerouth Ln, Key West, FL, 33040, United States
Do not fear mistakes. There are none.

Joe the Show ~ Rick's Bar Downstairs Stage
2026-02-13 16:00 - 20:00
Experience the electrifying performance of Joe the Show at Rick’s Bar Downstairs Stage in Key West. As a captivating musician, Joe brings unparalleled energy and charisma, transforming every night into a memorable musical journey. Enjoy a vibrant atmosphere with live tunes, refreshing drinks, and an unforgettable nightlife experience at Key West’s largest club.

Alex Anthony Duo at Hog's Breath Saloon
2026-02-13 16:30 - 2026-02-14 20:30
Experience the dynamic performance of the Alex Anthony Duo at the iconic Hog’s Breath Saloon in Key West. Known for their electrifying live music, Alex Anthony captivates audiences with a blend of vibrant tunes and engaging stage presence, making them a must-see act for music lovers visiting this lively dive bar.

World Famous 801 Girls- 5pm Show
2026-02-13 17:00 - 18:30
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 charisma and talent, these entertainers deliver unforgettable drag shows filled with energy and creativity. Join the 5pm show to witness the magic and embrace the vibrant nightlife atmosphere.

Barrett Thomas at Hank's Hair of the Dog Saloon
2026-02-13 17:00 - 20:00
Experience the captivating performance of musician Barrett Thomas at Hank’s Hair of the Dog Saloon in Key West. Known for his engaging live music, Barrett’s show promises a vibrant atmosphere perfect for a memorable night out. Enjoy Garbo’s food truck offerings and refreshing mojitos while savoring the sounds of a gifted entertainer.

Sunset Celebration at Mallory Square
2026-02-13 17:00 - 21:00
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 atmosphere. This historic waterfront location transforms with lively acts, local artisans, and delicious food vendors, all set against stunning sunset views, providing an enchanting experience for all ages.

Caribe of Key West at El Meson de Pepes on Mallory Square
2026-02-13 17:00 - 21:00
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 enjoy authentic Cuban cuisine, the band’s captivating rhythms set the stage for an unforgettable evening. Experience a fusion of culture and entertainment in this historic Key West locale.

Snacks and Five at Sunset Pier
2026-02-13 17:30 - 20:30
Experience the exhilarating performance of Snacks and Five at Sunset Pier, where Duval Street meets the Gulf of Mexico. Revel in their vibrant live music as you savor tropical seafood delights and refreshing mojitos. Set against breathtaking sunsets, this unforgettable Key West event promises lively entertainment and stunning waterfront views.

Pete & Larry Sloppy 2nds at Sloppy Joe's Bar
2026-02-13 17:30 - 21:30
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, they guarantee an evening filled with laughter and musical joy. Their engaging presence ensures an unforgettable night at this historic Key West venue.

JOE THE SHOW ~ Durty Harry's Stage
2026-02-13 18:00 - 21:00
Experience the electrifying performance of Joe The Show at Durty Harry’s Stage, located within Rick’s Entertainment Complex. Known for captivating audiences with his dynamic musical talent, Joe The Show promises an unforgettable night of live entertainment. Don’t miss this energetic musician at Key West’s bustling nightlife hotspot.

Turner Harrison at Tiki House Key West
2026-02-13 18:30 - 21:30
Experience an unforgettable evening at Tiki House Key West with the vibrant Turner Harrison. Known for his captivating performances and dynamic stage presence, Turner effortlessly blends genres, creating a unique musical journey. Dive into an island oasis while enjoying his charismatic and energetic artistry, making for an exhilarating night out.

NY Pauly at Irish Kevin’s Bar
2026-02-13 18:30 - 22:30
NY Pauly is the charismatic musician lighting up the stage at Irish Kevin’s Bar in Key West’s Old Town. Known for his energetic performances and magnetic connection with the audience, Pauly transforms each show into an unforgettable experience, making him a beloved staple of the lively entertainment scene on Duval Street.

Skidaddles Band at Schooner Wharf Bar
2026-02-13 18:30 - 23:30
Experience the vibrant sounds of the Skidaddles Band at the iconic Schooner Wharf Bar in Key West. Known for their energetic performances, they bring a unique blend of music to this historic open-air venue. Enjoy captivating tunes as you soak in stunning dockside views and the laid-back island atmosphere.

Scott Kirby With Mike Michaels at Key West Theater
2026-02-13 19:00 - 21:00
Join acclaimed musician Scott Kirby for an intimate performance at the historic Key West Theater. Known for his captivating acoustic style, Kirby delivers an unforgettable experience alongside Mike Michaels. Set in the charming Back Stage Listening Room, this event highlights Kirby’s engaging presence and musical talent in an iconic, newly renovated venue.

Magic Of Frank Everhart at Schooner Wharf Bar
2026-02-13 19:00 - 23:59
Experience the mesmerizing Magic of Frank Everhart at Schooner Wharf Bar, where this talented magician captivates audiences with his spellbinding performances. Set against the backdrop of Key West’s enchanting seaport, Frank’s magic is a must-see attraction, bringing wonder and excitement to this laid-back, open-air waterfront venue.

DJ Marty ~ Red Garter Saloon Stage
2026-02-13 19:00 - 2026-02-14 04:00
Experience the vibrant beats of DJ Marty at the Red Garter Saloon Stage in Rick’s Entertainment Complex, Old Town Key West. Renowned for his electrifying mixes and dynamic energy, DJ Marty crafts unforgettable nights in Key West’s liveliest club, surrounded by eight iconic bars and nonstop entertainment. Dive into an exhilarating musical journey!

LuffKiD at General Horseplay
2026-02-13 19:00 - 2026-02-14 22:00
Experience the magnetic energy of LuffKiD at General Horseplay in Old Town Key West. Known for his captivating performances, LuffKiD brings an electrifying blend of music that perfectly complements the lively atmosphere of this vibrant cocktail bar. Enjoy craft drinks, tasty bites, and unforgettable entertainment on Duval Street’s bustling nightlife scene.

Benmont Tench at Key West Theater
2026-02-13 20:00 - 22:00
Experience the musical brilliance of Benmont Tench at the Key West Theater. Renowned for his transformative artistry as a founding member of Tom Petty and the Heartbreakers, Tench captivates audiences with his masterful keyboard skills and evocative melodies. Join him for an intimate performance, showcasing his exceptional talent in this historic venue.

Karaoke at Two Friends Patio
2026-02-13 20:00 - 23:00
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 the vibrant atmosphere and engaging with the talented hosts who bring the event to life. It’s a must-visit for music lovers in historic Key West.

Elle Haley ~ Rick's Bar Downstairs Stage
2026-02-13 20:00 - 23:59
Experience the captivating performance of musician Elle Haley at Rick’s Bar Downstairs Stage. Known for her dynamic presence and mesmerizing vocals, Elle brings an unforgettable energy to Key West’s largest entertainment complex. Enjoy a night of live music and vibrant nightlife in the heart of Old Town Key West.
