Purpose A pilot study was conducted to assess correspondence among measures of program characteristics (opportunities and intervention strategies) and youth experiences in a range of activity settings in a residential immersive life skills (RILS) program. Method Opportunities and intervention strategies were assessed in 18 activity settings in the 21-day program. On two occasions each, four youth completed a measure of experiences and took part in onsite interviews. Results There was good convergence between observed program opportunities and the use of socially-mediated, teaching/learning, and non-intrusive strategies. Youth experiences of social interaction, choice, and personal growth were further informed by interview information. There was substantial convergence between program characteristics and youth experiences, indicating the program was provided and experienced as intended. Conclusions This pilot study indicated the fidelity of the program and the feasibility of using the measures in a future study. The preliminary findings suggest that RILS programs may provide a favorable environment for developmental experiences concerning social interaction, autonomy, and personal growth.