Working in different countries provides huge learning opportunities for theatre practitioners in understanding the capacity of drama pedagogies to uncover deep human connections beneath more superficial cultural differences, and to learn ways of negotiating the obstacles those cultural differences create. As recent years have brought more focus on both the social justice imperatives and the overall value of diversity and inclusion across schools and societies, the need to connect across cultures becomes ever more important. In this chapter we describe the journeys of our work exploring Shakespeare through intercultural dialogue with Omani colleagues. We describe the content and timeline of two interlinked multiphase education projects on Shakespeare with Omani teachers and students: the first with the Royal Shakespeare Company, which began as part of an education enquiry for the World Shakespeare Festival in 2012, and the second with Butterfly Theatre Collective, a small Meisner rooted company who specialise in exploring the uniqueness of every performance and performer. We offer a comparison of the practicalities in carrying out similar projects with two very different arts companies, and share the conceptual and emotional learning we found through our associations with Omani teachers, directors, actors and young people.