Existing standards for the audience measurement and vehicle valuation of a website depend heavily on the traffic information of separate web pages. As a result, the hyperlink structure of a website has not been properly examined. This study attempts to extend the scope of existing web advertising planning perspectives by redirecting attention to the relational characteristics of websites as advertising vehicles. With two measures developed from network analysis methods (network density and network centrality), the hyperlink structures of five popular portal/search engine sites are analysed and compared. Based on the analysis, this study develops a typology for classifying web pages and discusses how the typology can be used to design effective web advertisements.