Following the introduction of highly active antiretroviral therapy, an expanding cohort of adolescents with perinatally acquired HIV (PaHIV) is surviving and emerging from pediatric services with complex transition health care requirements. Transfer from pediatric to adult services has been associated with poorer health outcomes in other chronic diseases. Young people with HIV have the additional burden of stigma, secrecy, and the risk of transmitting HIV to partners and offspring. Maintaining engagement in health care during adolescence is critical. We compare reported satisfaction surveys of health care experiences and preferences of young people with PaHIV attending a U.K. transition outpatient service with young people attending a young persons' diabetes transition service in Australia. All 21 patients in the United Kingdom and 39 young people approached in Australia agreed to participate. The median age for both groups was 19 years, 67% of the PaHIV group were black African and 74% of diabetic group white Australian. Ninety-five percent (18/19) of those with PaHIV and 87% (34/39) with diabetes felt their transition was an easy process. Sixty-eight percent (13/19) of young people with PaHIV and 72% (28/39) of diabetic patients felt moving to their current service had a positive effect on their health. Being treated as an individual, comprehensive management explanations and encouragement to develop independence were cited as "strongly important" by over three quarters of participants with PaHIV. This service evaluation illustrates that careful transition can be a positive event for young people with PaHIV, comparable to that of a well-established diabetes services.