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Today's tourists seek authenticity and high-quality experiences. This chapter presents exploratory results from a tourist well-being project conducted in Madeira Island, Portugal. Using a tourism well-being scale, onsite and online data were collected in 2019. The study suggests that tourists with higher well-being are younger, have lower qualifications, are retired and/or students, first timers, and mainly Portuguese (mainland). Participants identify gastronomy, walk in nature, and landscape as the three most enjoyed activities/experiences. Results showed that tourists in Madeira want to have fun, experience something unique, and develop positive relationships. This study opens doors to offer customized experiences considering tourists psychological profile and their well-being.