Trip and conference chaperones are a wonderful resource in youth development programs. These well-intended volunteers, many parents of youth participating in the event, want the best experience for the youth but are not necessarily trained in positive youth development. A consequence of this circumstance is that not all chaperones provide the best opportunities for youth learning. Providing a card-based resource kit that allows for flexibility supports chaperones in running event meetings that are fun and engaging and that improve learning of content and development of life skills.