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  • Jeff Harris at Irish Kevin’s Bar - Irish Kevin’s Bar - 2026-04-17

    Jeff Harris at Irish Kevin’s Bar

    Irish Kevin’s Bar 211 Duval Street, Key West, Florida, United States

    Jeff Harris brings his captivating blend of music and comedy to Irish Kevin's Bar in Key West. As a talented singer, songwriter, and comedian, Jeff…

    Free

  • Distillery Tour – Key West Legal Rum Distillery

    Key West First Legal Rum Distillery 107 Simonton Street, Key West, Florida, United States

    Explore the captivating Key West Legal Rum Distillery located in the Historic Seaport, offering an engaging atmosphere with daily free tours and tastings. Delight in…

    Free

  • Mojito Class by Key West Legal Rum Distillery – Min 4 people

    Key West First Legal Rum Distillery 107 Simonton Street, Key West, Florida, United States

    Join the Mojito Class at the Key West Legal Rum Distillery, where a talented entertainer guides you through the art of crafting the perfect mojito.…

    $75.00

  • Glass Bottom Boat Cruise – Key West’s Window to the Sea

    Fury Key West- Departure Point 2 0 Duval St, Key West, Florida, United States

    Join the Glass Bottom Boat Cruise in Key West for a captivating evening of ocean exploration. Highlighting a talented entertainer, the cruise combines marine beauty…

    $69.95
  • New Moon Magic w/Mermaid Dorian - Southernmost Beach Resort - 2026-04-17

    New Moon Magic w/Mermaid Dorian

    Southernmost Beach Resort 1319 Duval Street, Key West, Florida, United States

    Experience the enchanting world of Mermaid Dorian at New Moon Magic. Join this captivating entertainer on South Beach for an afternoon of swimming, storytelling, and…

    Free

  • Elle Haley at Hog’s Breath Saloon

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

    Elle Haley enchants audiences with her soulful performances at Hog's Breath Saloon in Key West. As a vibrant musician from the Florida Keys, she captivates…

    Free

  • Wynn Taylor at Rick’s Bar Downstairs Stage

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

    Wynn Taylor, a charismatic singer-songwriter from Lexington, captivates audiences with his soulful roots music at Rick's Bar Downstairs Stage in Key West. An Army veteran…

    Free

  • Brian Roberts at Sloppy Joe’s Bar

    Sloppy Joe's Bar 201 Duval St, Key West, Florida, United States

    Brian Roberts, a talented singer/songwriter from the Florida Keys, enchants audiences with his captivating live performances at Sloppy Joe's Bar. His engaging presence and soulful…

    Free
  • Tony Baltimore at Schooner Wharf Bar - Schooner Wharf Bar - 2026-04-15

    Tony Baltimore at Schooner Wharf Bar

    Schooner Wharf Bar 202 William St, Key West, Florida, United States

    Experience the musical artistry of Tony Baltimore at Schooner Wharf Bar in Key West. This talented singer/songwriter blends alternative roots-rock with captivating originality. Raised by…

    Free
  • DEAD FEST KEY WEST - April 17, 18, 19 - 2026 - The Alamo Key West - 2026-04-17

    DEAD FEST KEY WEST – April 17, 18, 19 – 2026

    The Alamo Key West 4 Charles Street, Key West, Florida, United States

    Join us for DEAD FEST KEY WEST 2026, a thrilling free festival celebrating the Grateful Dead's legacy. Headlined by the electrifying STEELY DEAD, the event…

    Free

  • Mike Stack & DLew at Tiki House Key West

    Tiki House Key West 203 Duval Street, Key West, Florida, United States

    Experience the innovative synergy of Mike Stack and DLew at Tiki House Key West. This dynamic duo captivates audiences with their blend of strategic insight…

    Free