Educational transitions take place when children move from home to start early childhood education and from primary school to secondary school then to universities and other tertiary institutions. Internationally, women are transitioning into tertiary education, achieving higher qualifications and securing jobs in areas that were once male dominated. Women in Papua New Guinea (PNG) are also entering tertiary education within PNG and abroad despite facing the barriers imposed by a male-dominated society, socio-cultural and socio-economic constraints and other setbacks which challenge their sense of self as women from PNG. The National Gender Equity Policy (2003) clearly advocates for fair and equal educational opportunities to be given to the female gender in PNG. However, the challenges and experiences of educational transition to university for female students from both urban and rural areas in PNG have not been researched to date. The main aim of the study was to explore and document educational transition experiences for female students from secondary to tertiary education in PNG. The study examined the students’ choices, challenges and sources of support. It also considered factors they perceived as possibly contributing to success and failure with university courses. A qualitative approach was used to gather data from twelve young women, six from urban settings and six from rural settings, in a university in PNG. Semi-structured and focus group interviews were used, with a thematic approach for data analysis to provide a comprehensive knowledge of their experiences of educational transition. The key findings showed that the participants made their own choices about choosing university study. Parents, teachers and other people inspired and acted as role models for the young women and initiated their interests in further education. It was evident that the socio-cultural context of PNG had a considerate impact on the choice of the young women. Both positive and negative stories were presented to the young women; however, they resisted the negative comments and pursued their education. Some men acted as role models and used their power within a patriarchal society to disrupt existing patterns to support women in education. Wider family involvement is a feature of PNG life and should be considered as having an important role in supporting transition. Upon entering the new micro-system of the university the young women encountered academic, social and welfare challenges which had an impact on their sense of self. They displayed different characteristics, including unconfidence, nervousness and despondency. However, the university provided a positive learning environment with its resources that encouraged and motivated learning to take place over time. The young women sought help and assistance from their families, lecturers, friends and others around them to sustain their transition to university. Having access to friends’ resources is an important determinant when negotiating transitions. Overall, the young women’s positive characteristics of interactions and interconnected relations with others in the new micro-system of the university played an important role in their transition. This study suggests that to enable more women to make a successful transition to university parental support, role modelling and cultural change are essential. This process will require the support and cooperation of all stakeholders.