Over the past three decades, travel to Poland for youth and young adults has become increasingly popular, to the extent that it is even seen as a "rite of passage" for members of many Jewish communities. For these groups, the accompanying guides or educators are central to their educational experience. Based on a series of interviews with educational guides, this article sets out to understand the trips from the perspective of the guides. A deeper appreciation of the guiding experience--the guides' goals and reflections--will enable a more holistic understanding of these trips.