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  • Trenton Chandler at Rick’s Bar Downstairs Stage

    Rick's Entertainment Complex 202 Duval Street, Key West, Florida, United States

    Trenton Chandler, a talented country musician from Shallowater, Texas, graces Rick's Bar Downstairs Stage in Key West. Influenced by the timeless sounds of Buddy Holly…

    Free

  • 801 Karaoke – Hosted by Jeff

    801 Bourbon Bar 801 Duval Street, Key West, Florida, United States

    Join Jeff for a lively karaoke night at 801 Bourbon Bar, nestled in the heart of Old Town Key West. This vibrant venue, known for…

    Free

  • Adam Lufkin Duo at Hog’s Breath Saloon

    Hog's Breath Saloon 400 Front St, Key West, Florida, United States

    The Adam Lufkin Duo, led by the dynamic vision of Adam Lufkin, captivates audiences with their unique blend of reggae, hip-hop, and rock. Performing live…

    Free

  • World Famous 801 Girls- 5pm Show

    801 Bourbon Bar 801 Duval Street, Key West, Florida, United States

    Experience the captivating World Famous 801 Girls in their dazzling 5pm show at 801 Bourbon Bar. Nestled in Old Town Key West, these iconic drag…

  • QMitch Drag Queen Bingo at 22&Co

    22 & Co 504 Angela Street, Key West, Florida, United States

    Join the fabulous QMitch for an unforgettable night of Drag Queen Bingo at 22&Co in Old Town Key West. Known for captivating performances and sparkling…

    Free

  • Sunday Jazz at the Gardens

    The Gardens Hotel 526 Angela Street, Key West, Florida, United States

    Experience the enchanting Sunday Jazz at the Gardens, where the lush tropical setting of The Gardens Hotel comes alive with the soulful melodies of talented…

    Free

  • Jay Klein at Hank’s Hair of the Dog Saloon

    Hank's Hair of the Dog Saloon 409 Caroline Street, Key West, Florida, United States

    Jay Klein, a dynamic musician and tech enthusiast, captivates audiences at Hank's Hair of the Dog Saloon in Key West. Known for his innovative performances,…

    Free

  • Rick Fusco at Rams Head Southernmost

    Rams Head Southernmost 804 Whitehead Street, Key West, Florida, United States

    Experience the captivating musical talent of Rick Fusco at Rams Head Southernmost. As a seasoned musician, Rick mesmerizes audiences with his dynamic performances in this…

    Free

  • Caribe of Key West at El Meson de Pepes on Mallory Square

    El Meson De Pepes Restaurant and Bar 410 Wall Street, Key West, Florida, United States

    Enjoy a captivating performance by Caribe of Key West at El Meson de Pepes on Mallory Square. Delight in the vibrant ambiance and live Cuban…

  • Sunset Celebration at Mallory Square

    Mallory Square 1 Whitehead Street, Key West, Florida, United States

    At the Sunset Celebration at Mallory Square, witness mesmerizing performances by talented entertainers like the iconic cat man. As jugglers and street performers captivate audiences,…

    Free
  • Shanty Hounds at Two Friends Patio Restaurant - Two Friends Patio Restaurant - 2026-04-12

    Shanty Hounds at Two Friends Patio Restaurant

    Two Friends Patio Restaurant 512 Front Street, Key West, Florida, United States

    Join the Shanty Hounds at Two Friends Patio Restaurant for an entertaining evening with the talented acoustic duo of Dani Hoy and Key West Chris…

    Free

  • Xperimento Soundcheck Set at Green Parrot Bar

    Green Parrot Bar 601 Whitehead Street, Key West, Florida, United States

    Experience the dynamic rhythms and vibrant energy of Xperimento at the iconic Green Parrot Bar in Key West. This talented ensemble brings their unique fusion…

    Free