This study investigated the effect of tour leader playfulness on the quality of interactions between tour members and leaders, tour leader attachment, and tour member delight. The study employed a cross-level approach by considering the perspectives of both tour leaders and tour members participating in group package tours. A questionnaire survey was conducted to obtain insights from both perspectives. A total of 54 sets of samples (including 54 tour leaders and 520 tour members) were collected. The results demonstrated that tour leader playfulness had a positive effect on tour member delight, interaction quality, and tour leader attachment. Furthermore, the study validated the mediating effects of interaction quality and tour leader attachment. By integrating social exchange theory with dramaturgy theory, group dynamics, and attachment theory, this study extends the theoretical gap in research on tour guide playfulness. Practical suggestions for tourism operators and managers are also provided.