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  • Jam Night Mondays, GT Post

    The Outpost at Rackams, George Town Waterfront

    Join The Outpost at Rackams for Jam Nights! Join other musicians and enjoy creating/listening to live music. Drink specials and the largest variety of imported craft beers exclusive to this […]

  • Stingray Award 2025

    Grand Cayman Marriott Beach Resort , Cayman Islands

    The Stingray Tourism Award is an annual event hosted by the Cayman Islands Tourism Association (CITA), celebrating excellence within the tourism and hospitality industry of the Cayman Islands. The event honors individuals, […]

  • International Scuba Diving Hall of Fame

    Hotel Indigo Cayman Islands , Cayman Islands

    Join us for an unforgettable evening as we honour the first-ever all-women cohort inducted into the International Scuba Diving Hall of Fame. Set against the stunning backdrop of the Hotel […]

  • Wine & Cheese Tasting

    Le Petit Bar

    Le Petit Bar Tasting Series 2025–2026 From September 30 to May 28, LPB transforms into a world of unforgettable wine & spirits adventures — from rare Bordeaux verticals and Escape-the-Cellar puzzle nights to indulgent pairings […]

  • Restaurant Month

    This October the Cayman Islands Tourism Association marks the 12th anniversary of Restaurant Month, a vibrant celebration of Cayman’s diverse and outstanding culinary scene. For 31 delicious days, local restaurants […]

  • Pilates for Pink 2025

    Camana Bay ARC Centre, Cayman International School

    Pilates for Pink 2025 – Heart + Core Date: Saturday, October 4, 2025 Location: ARC, Cayman International School Time: 9:00 AM – 10:00am – Pre Pink Party, 10:00am – 11:00am […]

  • Miss Global International 2025

    Hotel Indigo Cayman Islands , Cayman Islands

    The Annual Miss Global International Pageant Returns to Cayman! This October, the Cayman Islands proudly hosts the empowering and highly-anticipated Miss Global International Pageant for its 21st edition, a beacon […]

  • 2025 World Mental Health Day Symposium

    Camana Bay Cinema

    Attendees will have the opportunity to experience a variety of sessions led by Infinite Mindcare’s team of Masters and PhD CPAM-registered therapists. Every hour there will be four (4) sessions […]

  • Cayman Wine Fest

    Westin Grand Cayman Beach Resort

    Tortuga’s Annual Wine & Spirits Festival Returns to Cayman! This October, Tortuga brings back its much-anticipated Wine & Spirits Festival for its fifth sensational year– a vibrant celebration of flavour […]

  • Women Empowerment Brunch Empower HER

    Kimpton Seafire Resort , Cayman Islands

    Now in its fifth year, the brunch has become the most anticipated event of its kind, selling out each year while uniting a diverse group of women to empower and […]

  • Spotlight on Memories

    Harquail Theatre, FJ Harquail Cultural Centre , Cayman Islands

    Jasmine’s Spotlight returns to the Harquail Theatre on October 17–19 with this year’s theme, Spotlight on Memories —a musical journey through the decades, bringing back timeless and unforgettable hits. With dynamic […]

  • Salud 2025

    Hotel Indigo Cayman Islands , Cayman Islands

    Cayman’s premier wine experience showcasing over 150 quality wines from leading producers of the world’s finest wine-growing regions.