The term Web 2.0 was coined around 2004 and was used to describe more interactive types of websites developed after the dot-com crash. An important characteristic of Web 2.0 sites is premised on being able to incorporate various technologies and applications within the site to enhance functionality. This enhanced functionality is primarily associated with such sites being able to publish and display diverse content— content that is user-contributed, or where the site might draw information synergistically from a third party. This increased functionality potentially affects two traditional areas of website implementation. Firstly, the embedding of applications within a website tends to increase design complexity that can contribute to a detrimental user experience when browsing— in turn, affecting website usability. Secondly, Web 2.0 sites in allowing users to publish, display and list diverse views, opinions, pictures, sounds, and so forth, will impact content and design features that are not encountered on traditional websites. Consequently, this chapter investigates a set of Web 2.0 tourism sites for their usability as well as reporting an overview of website content encountered. In examining these issues the paper provides a background primer on the advent of Web 2.0 sites, novel aspects of their design, including the potential for incorporating user content. Tourism sites are the focus of this chapter— both commercial and noncommercial Web 2.0 sites being of interest.