Abstract: High attrition rates have been a consistent occurrence among online learners, creating the challenge of how to design online instruction for the type of learning that encourages student engagement. With new technologies constantly evolving, the question becomes how educators can use these new web-based applications to engage students and possibly resolve the problem of high attrition among online learners? The purpose of this study was to assess the level of learning engagement through student participation in The Panhellenic Project, an instructional design model that integrated constructivist learning principles with Web 2.0 technologies. Additionally, the usefulness of structured orientations to the Web 2.0 technologies and the effectiveness of these technologies was also investigated. Using a mixed-methods case study design, The Panhellenic Project was framed around a collaborative group activity where undergraduate students worked in teams with the task of creating a three-dimensional virtual ancient Greek Parthenon and one ancient Olympic game event within the Second Life virtual world. A project wiki was established for student-participants to research sports history as well as share knowledge, information and resources. An informational blog with project resource information was developed as a Second Life learning reference. Multiple sources were used to capture data including the Survey of Student Engagement, pre- and post-project questionnaires, and electronic discourse analysis of wiki posts and Second Life chat transcripts. Research finding showed that the majority of the student-participants were engaged in The Panhellenic Project and that learning had occurred over the length of project implementation. The structured orientation and training sessions were perceived as effective in connecting theoretical and practical knowledge, though not effective for teaching students to use the Second Life virtual world. Overall, the level of difficulty experienced in learning the application influenced student-participant perceptions about the effectiveness of the Web 2.0 technologies used in this study. Further, analysis of the data revealed that the participants consistently demonstrated constructivist learning activities through interaction with other learners, collaborative teamwork and the sharing of multiple perspectives as they completed The Panhellenic Project.