Teachers today are expected to develop lessons that not only teach students academic content knowledge, but help them develop 21st Century Skills that enable them to be effective team players, inventive thinkers, active problem solvers, and digital literate citizens (Partnership for 21st Century Skills 2004; Solomon and Schrum 2007). Emphasis on 21st Century Skills arises from a firm belief that only with these skills can students succeed in a globally competitive world where interconnectivity, knowledge production and technological innovations are essential to productivity and success. Web 2.0 is a term referring to various emerging web-based technologies that allow users to (1) share knowledge through collaborative editing, communicating, publishing, and commenting and/or to (2) dynamically change the content of knowledge published on the web. With such affordances, Web 2.0 and virtual world technologies are rapidly gaining attention from educators globally. Meaningful incorporation of these applications alongside constructivist pedagogical approaches (e.g., project-based learning, inquiry based learning, cooperative learning, or etc.) are believed to help cultivate 21st Century Skills (Moylan 2008).