Tourist guides embrace multiple roles in a given day. Their contributions to developing tourism include a mediating role (brokering access, encounters, understanding and empathy), as interpreters, storytellers, timekeepers and psychologists. Although Tourist Guides’ contributions to sustainability are documented in academic literature, it is timely to revisit these a decade later. Namely, there are eight sustainability outcomes that depict eight instances of how Tourist Guides can contribute to meeting these outcomes. Tourist Guides act to enhance tourists’ understanding of communities, cultures and the environment. Tourist Guides can monitor and influence tourist behaviour and foster post-visit attitudes which ensure repeat visitation. This paper presents a fresh twist to Tourist Guides roles by introducing the Character Strengths (CS) approach into the equation. A simple yet rather profound proposition is made: truly sustainable tourism provides avenues for Tourist Guides to flourish and experience well-being if they nurture and apply the right Character Strengths for the specific role in that moment. Grounded in positive psychology, the Values-in-Action Classification of Character Strengths and Virtues (VIA-CS) approach is grounded in optimism and resilience. VIA-CS can be understood through the PERMATM Theory of Well-Being which proposes five pillars (Positive emotions, Engagement, Relationships, Meanings, Achievements) as pathways to leading the good life. Character Strengths are the bedrock of the human condition, and strength congruent activity represents an important route to the psychological good life. Character Strengths are the psychological ingredients for displaying virtues or human goodness. The VIA-CS model includes 24 values within six dimensions (wisdom & knowledge, courage, humanity, justice, temperance and transcendence). By embedding the VIA-CS into Tourist Guide training practices, Tourist Guides roles and sustainability outcomes can be nurtured to ensure every Tourist Guide flourishes whilst providing quality tourism experiences for tourists. Ultimately, any discussion on sustainable tourism for the future has to be reminded that nothing comes close to the role of a Tourist Guide. Therefore, it is imperative we nurture and equip our Tourist Guides with the VIA-CS toolkit.