This paper is a discussion of the development of graduate programs in Nassau and Freeport, Bahamas. In 2010, our university made a conscious decision to offer an off-shore graduate program to Bahamian educators, at one specific site (one island), in response to a particular request. Today, we offer five different programs at three sites (2 islands) to teachers, school administrators, counseling professionals and organizational leaders across a range of institutional contexts. To date, over 20 professors from our School of Education have traveled in order to provide face-to-face off-shore instruction to Bahamians wishing to continue their education, in order to enhance professional learning and growth. Several of the administrators and faculty members who have been involved have begun to examine their experiences, individually and collaboratively, and are exploring the possibilities of future expansion of the international program, due to the success of the graduate programs offered in the Bahamas. This paper describes one of these sites, and the experiences of one administrator and one faculty member, of teaching, lessons learned, and suggestions for institutions of Higher Education considering developing off-shore graduate teacher education, educational services and organizational leadership programs.