In this paper, we present a two-part study. The first part was a cultural appreciation study. Through this study, we explored the specific approach of cross-cultural aesthetic appreciation and mapped out the potential insights for a prototype design. In the second part, we carried out a design-led study. We designed a tablet application and conducted focus group studies to explore the interactive technology that assists in the support of cross-cultural audiences’ aesthetic appreciation and engagement of traditional Chinese painting. Based on these findings, we went on to further explore an approach of interactive engagement which is specific to supporting cross-cultural appreciation, while also reflecting upon the interactive design suggestions for the development of aesthetic appreciation to offer various transferable insights to the Human–Computer Interaction (HCI) community.