In this article, the author describes the Jazz Workshop, a unique blend of collaboration and constructivist learning using videoconferencing and Web 2.0 tools. Each summer it draws about 400 participants--mostly teachers, technology facilitators, teacher librarians, and videoconferencing coordinators--who convene in 20 locations across three countries and five states. Facilitators who have attended the workshop in the past as participants host the workshop at each of the sites, and lead facilitators, who have several years of experience with videoconferencing and at least two years of experience facilitating the workshop, organize the event. The goal of the Jazz Workshop is to teach participants how to integrate videoconferencing into their curricula.