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This paper addresses usability issues in city tourism Web site design. Through content analysis, the paper examines the content and functions of fifty-five city tourism Web sites covering North America, Europe, Asia, Australia and Africa. The paper analyzes the characteristics of city tourism Web sites and target users. It generalizes the existing literature and identifies key factors influencing city tourism Web site usability. The paper focuses on usability challenges and analyzes cross-cultural differences on city tourism Web sites. It reports the content analysis data and provides suggestions for making tourism Web sites more effective, efficient and easy-to-use.