This submission to the special interactive session aims to develop testable design conjectures for a design-based research project involving a youth sailing camp. Youth sailing involves intensely immersive embodied experiences in boats, but also reflection on broader principles and processes. Coordinating between these two levels is often difficult for youth, particularly over a short time frame in an interest-driven environment. We present two existing tools that we believe have the potential to bridge this difficult conceptual and motivational gap, but involve very different epistemological hurdles. Using both existing footage of the tools in action and interactive reworking, we hope to collaborate with other participants to further specify the affordances and constraints of these tools, and potentially more effectively hybridize them toward our curricular goals.