The author reflects on her experience as an ethnographer accompanying a family trip to Israel from Congregation B'nai Jacob (CBJ). She explores three dimensions of the experience that she believes were uniquely attributable to the fact that this was a trip taken with fellow congregants. First, she examines how the trip built community among the participants. Next, she describes how the trip invited the participants to explore questions of religious development. Finally, the author reflects on how the role of Conservative Judaism in Israel was used by the rabbi and the guide as the lens through which the participants were encouraged to see and define a relationship to the land and the people of Israel. The author argues that the richness of an Israel experience and its ability to retain a place in American Jewish Life lies in its complexity. If trip planners and educators hope to help participants expand the depth of their understanding about how Israel and Judaism intersect, the author argues that the trip structure must risk introducing dissonance since this will allow for both critical thinking and shared community, teach people to be comfortable in seeking questions, help them recognize their inherent biases, and keep Israel as a dynamic force in their lives.