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This study examines the extent to which Generation Y (Gen Y) serves as an opportunity or challenge for visitor attractions in the UK and the corresponding strategies adopted to seek engagement with this generational segment. A multiple-case study design was adopted with face-to-face interviews undertaken with senior personnel at leading visitor attractions across the UK. The paper advances a number of marketing and experiential strategies before advocating that further research is required to explore the growing pains of Gen Y from ‘adolescence’ to ‘adulthood’ if the industry is going to be able to understand, meet and hopefully exceed their needs, wants and expectations in the challenging years to come.