Background: Many children who contracted Human Immunodeficiency Virus (HIV) through vertical transmission are now in their adolescent and early adult years. The aim was to explore the experiences of adolescents living with HIV (ALWHIV) during the transition from childhood to adulthood. Methods and Material: The study was conducted at selected primary healthcare facilities in the Mopani and Vhembe districts in July 2021. A qualitative research approach that included contextual, descriptive, and exploratory designs was used. The population comprised 27 ALWHIV who were purposively sampled and enrolled for ART care. Data were collected using in-depth interviews, and the question was“How is it for you as you live with a virus and transit from adolescent to adulthood”.The open coding approach was used to analyse the data. Measures to ensure trustworthiness articulated in Lincoln and Guba’s criteria and ethical considerations were adhered to. Findings: The findings revealed four themes: poor understanding of the disease condition, improved physical health when adhering to ARV treatments, challenges related to sexual maturity and intimate relationships, and parents not disclosing their children’s HIV status. Conclusion: Parents’ delayed and non-disclosure of adolescents’ positive HIV status led to a lack of awareness about the course of the disease, non-adherence to ART, and unsafe sex practices that could increase the risk of HIV transmission and re-infection. To address these multiple obstacles associated with ALWHIV, a comprehensive, multi-sectoral approach that is teenager-friendly should be undertaken.