Travestisand transgender women (TrTGW) constitute the groups with the highest HIV prevalence in the world, with higher probability of infection compared with the general population and lower adherence to prevention and treatment strategies than other vulnerable groups. Considering these challenges, this study describes the factors associated with the retention of TrTGW with HIV to the TransAmigas project. Participants were recruited from April 2018 to September 2019 in a public health service in São Paulo, Brazil. A total of 113 TrTGW were randomly assigned to either a peer navigation intervention (75) or a control group (38) and followed up for nine months. To analyze the association between the selected variables and the outcome (“retention at nine months”, regardless of contact at three months, defined by the “full completion of the final questionnaire”), bivariate and multivariate logistic regression models were used. Peer contact forms were qualitatively assessed to validate and complement the previous selection of quantitative component variables. Of the 113 participants, 79 (69.9%) participated in the interview after nine months, of which 54 (72%) were from the intervention group and 25 (66%) from the control group. In the final multivariate model, contact at three months (adjusted odds ratio – aOR = 6.15; 95% confidence interval – 95%CI: 2.16–17.51) and higher schooling level (≥ 12 years) (aOR = 3.26; 95%CI: 1.02–10.42) remained associated with the outcome, adjusted by race/skin color, age ≤ 35 years, and HIV serostatus disclosure. Future studies with TrTGW should include contact at regular intervals, with additional efforts aimed at participants with lower schooling level.