Firms and organizations are increasingly exploiting electronic channels to reach their customers and create new business opportunities. To this end, electronic shops have been developed, either offering products from a single firm or encompassing multiple individual electronic stores, comprising thus electronic shopping malls. Besides development activities, electronic shopping has attracted the attention of researchers, who have studied various perspectives, including user attitude, critical success factors, security, technical aspects, and so forth (e.g., Fang & Salvendy, 2003; Wang, Makaroff, & Edwards, 2003). Two main concerns for e-commerce are personalization and enhancement of user experience. Personalization addresses the ability to offer content tailored to the preferences of each user (Anupam, Hull, & Kumar, 2001) or user group (Wang et al., 2003). Preferences may be explicitly declared by the user, or derived by the system through inspecting user interaction; if the system dynamically reacts to changes of visitor behavior, it is termed as adaptive. Personalization allows customers to focus on the items they are interested in, and enables electronic shops to make targeted suggestions and send promotions to customers (Lekakos & Giaglis, 2005). Enhancement of user experience is another major issue in e-commerce, given that 2D images and texts on the screen are not sufficient to provide information on product aspects such as physical dimensions, textures, and manipulation feedback (Park & Woohun, 2004). Major e-commerce categories that could benefit from giving a more accurate and/or complete view of the products include real estate brokers who could present detailed models of properties, furniture stores that could allow their customers to view how certain pieces would fit in the target place (Hughes, Brusilovsky, & Lewis, 2002), and clothing shops that could provide a virtual fitting room with customizable avatars (Compucloz Corporation, 2003). Multimedia presentations can also be used as a means for “information acceleration” for promoting “really new” products (Urban et al., 1997). Enhancement of user experience may finally compensate for the loss of the pleasure associated with a visit to a shopping mall (Laskaridis, Vassilakis, Lepouras, & Rouvas, 2001). Nowadays, the technological potential of Internet systems provides adequate means for building online multimedia applications that can help e-commerce sites attract e-shoppers. Applications can be built to adapt to the user’s profile and provide the user with a suitable set of information in the most efficient way. Virtual reality (VR) technologies are also now mature enough to be used for the wide public, offering vivid and highly interactive environments, allowing users to view synthetic worlds within which they can visualize and manipulate artifacts. This article aims to specify a system that exploits capabilities offered by adaptation and VR technologies to offer e-shoppers personalized and enhanced experiences, while addressing challenges related to the cost, complexity, and effort of building and maintaining such a system.