Moving away from a product-logic focussed luxury literature, this chapter follows the need for greater attention on the experience dimension of luxury. Focussing on luxury yachting (superyachting), the chapter outlines how the luxury experiences involve co-creation through multi-sided interactions and, significantly, how in this mutual co-value creation process, technology (digitisation and social media) is playing an increasingly important role. This increase in part follows the developments in technology that enable parties to play a more active role in service interactions. It also in part follows the rise of the technologically capable Gen Z group of consumers, many of whom have the high net worth to be luxury yacht charter consumers. The chapter also outlines some of the dilemmas involved in promoting hedonic luxury experience propositions. Notably, these include how the essence of the experience that makes it a luxury one can be presented through the Internet and social media. Additionally, how the ‘Internet dilemma’ associated with the democratisation of luxury through social media can influence luxury perceptions. Using data captured from the luxury yacht industry, the chapter first sets out how the industry currently presents luxury online. It then proposes strategies on how to improve the design of their digital promotions to effectively convey luxury yacht charter value proposition offers, particularly regarding its experience-oriented dimensions.