Families are an important context for learning astronomy, one that researchers on astronomy teaching and learning have largely overlooked. At public observatories, families have an opportunity to learn both the substance and practices of astronomy together. However, the typical structure of public observations (one visitor looking through a telescope while an expert explains what they see) creates tension with families engaging in the disciplinary practice of building disciplined perception through collaborative sensemaking. In this paper, we report on a preliminary study in which a family pilot tested new activities to encourage collaborative sensemaking. Key factors that supported the family's collaborative learning include (1) Using activities that shift authority and control to each member of the family, (2) Having a variety of activities that can be deployed at strategic times rather than a fixed schedule, and (3) Being responsive to the family dynamics, including the emotional needs of each family member.