This paper explores the potential of technology and artificial intelligence (AI) to revolutionize leisure sailing experiences by dynamically tailoring onboard environments to individuals’ emotions and preferences. Traditionally, leisure activities have been somewhat static, offering limited scope for personalization. However, advancements in sensor technology and AI systems have opened new possibilities for enhancing well-being and enjoyment during leisure activities. Using leisure sailing as a case study, this paper demonstrates how onboard sensors and AI systems can respond in real-time to participants’ emotions, adjusting various environmental factors such as lighting, music, ventilation, colours, and furniture layout to optimize comfort and enjoyment. By harnessing the power of technology and AI, leisure sailing experiences can be personalized and enriched, leading to enhanced relaxation and joy for participants. Furthermore, this paper encourages discussions on the broader potential of technology and AI to elevate leisure experiences across different domains. By focusing on advancements, applications, and ethical considerations, it aims to deepen our understanding of personalized and engaging leisure experiences. By fostering collaborations between technology developers, leisure industry professionals, and researchers, this paper seeks to inspire the creation of innovative solutions that reshape the future of leisure. In summary, this paper envisions a future where leisure sailing experiences are enhanced through seamless integration of technology and AI. By dynamically adapting to individuals’ emotions and preferences, the onboard environment can be optimized to maximize comfort and happiness, providing a truly personalized and engaging leisure experience.