In this piece, we put forth a Deweyian framework for youth development activities in outdoor and adventure education programs, and we show how such a framework may be exemplified by activities in sail training and sailing instruction. The paper begins with a discussion of the theoretical features of Deweyian educational experiences and makes connections between these ideas and positive youth development. We then, by reference to the educational activities aboard vessels large and small, provide concrete illustrations of these theoretical features. The goal of the paper is to propose a framework that educators in outdoor and adventure programs--and in youth development programs generally--can employ to bring Dewey's ideas to bear on program design and assessment.