This article describes the SS "School Library Leadership" maiden voyage, which departed from the University of Vermont (UVM) during the 2010 fall semester. Twelve intrepid sailors followed their sense of adventure into uncharted waters with cocaptains Judy Kaplan and Susan Ballard in an online collaboration that provided a powerful learning experience for all. The metaphor of the voyage set the scene for an interactive experience that transcended time constraints and geographic isolation, and encouraged networking and collaborative projects. Facilitators and participants explored leadership roles and opportunities for school librarians (SLs), as they examined their own practices and educational environments through an inquiry-based model based in an asynchronous online graduate-level course School Library Leadership for 21st-Century Schools. In addition, the instructors provided a working model of coteaching and reflective practice. Building on concepts found in AASL's "Learning4Life National Implementation Plan" (L4L) to provide support for "on the ground" practitioners, a new series of online courses offered by UVM for school library professionals in practice provides opportunities to focus on current issues within education and school librarianship in a sustained and supportive learning environment. The key component of the coursework is collaboration between both the facilitators (instructors) and the participant SLs. Learning from and with colleagues in a professional learning community, or community of practice, is demonstrated to be a best-practice model for transformational learning.