Consumer purchasing online is considered, with interactivity highlighted as a critical end-user issue. Levels of user interactivity up to and including virtual reality environments are now realistic in e-tailing. Conceptualizing interactivity to recognize the relevance of perceptions to consumer engagement motivates a focus on the user interface. Aspects relating to trust, usability and involvement are identified, and examined in a series of linked studies focusing on hedonic and high-involvement products, particularly surfboards. Preliminary studies across a range of businesses and products indicated consumer willingness to purchase hedonic products online, but many businesses imposed a high workload on online purchasers. Despite successful web marketing of hedonic products such as CDs, we found that no contemporary providers of customized surfboards offered finished product e-tailing, nor used virtual reality technology to demonstrate performance. A real case study of online swimwear purchase demonstrated an improved purchase process. “Beachtown”, a virtual reality e-tailing environment related to a coastal tourism economy allowed further examination of apparel, surfboard and holiday purchase. Results indicate that an enhanced interactive virtual environment increases end user involvement and willingness to purchase.