Background: Individual differences have been seen to play a key role in spatial orientation. Gender implications have been previously described but little is known about how other variables, such as wayfinding anxiety, emotional difficulties and wayfinding experience can mediate this relationship. Methods: A group of 269 participants were involved in this study and completed questionnaires on their self-reported allocentric orientation strategy, wayfinding experience and satisfaction with the ability for wayfinding. Emotional outcomes were also investigated: spatial and trait anxiety, neuroticism, difficulties in emotion regulation, and personal safety. First, a principal component analysis was conducted and the studied variables were grouped into four components: outdoor wayfinding experience, wayfinding-related fear, emotional difficulties, and effective wayfinding skill. Afterwards, structural equation modelling was performed, using the MPLUS statistical program. Results: The results showed that gender constitutes a predictor for using an effective wayfinding skill and for feeling wayfinding-related fear. However, outdoor wayfinding experience, wayfinding-related fear and emotional difficulties did not mediate the relationship between effective wayfinding skill and gender. Conclusion: These results highlight the differential contribution of gender in the emotions that are experienced during spatial orientation and emotions that are related to other types of situations. The limitations, strengths and theoretical implications of the proposed model are discussed. Further investigation is needed in order to understand the role of emotions in spatial orientation.