Background: Tall ship sail training, a form of outdoor adventure education, has historically been used with youth to build competency in seamanship and social and emotional skills. However, there is a void in the literature documenting precise program models connected to specific goals. Purpose: This paper presents a case study of the Shenandoah Model of sail training. It details its Positive Youth Development (PYD) framework and mean changes in PYD assets reported by participants. Methodology/Approach: Participants were surveyed using a one-group retrospective pretest-posttest pre-experimental design to assess the impact of participation. Findings/Conclusions: The participants reported significant mean increases across all PYD assets (Caring, Connection, Contribution, Competence, Character, Confidence, and Happiness), including moderate effect sizes for all measures except Happiness. In addition, over 70% of the participants would recommend the program and/or do it again, suggesting program satisfaction. Implications: Connecting different PYD assets to various program activities allows future program designs to intentionally develop sail training voyages to build competencies. Future follow-up research is needed, including qualitative methods to capture the impact of these programs from the participants’ viewpoint.