Background/Objectives: Adolescents and young adults (AYA) with sickle cell disease (SCD) face challenges related to the disease and its treatment. The Transition Readiness Assessment Questionnaire (TRAQ) is a self-report tool for assessing transition readiness for youth with special health care needs (YSHCN), including SCD. This study uses the TRAQ to understand transition readiness in patients with SCD treated at the Boston Medical Center, evaluates associations between TRAQ scores and transition outcomes (e.g., EDr, EDu), and compares TRAQ scores in this population with other YSHCN. Methods: We reviewed electronic medical records of AYA with SCD who completed the TRAQ in the pediatric hematology clinic between January 1, 2019, and March 1, 2020, and categorized healthcare encounters to calculate EDu and EDr. We used t-tests and ANOVA models to analyze mean TRAQ scores, sex, age, genotype, EDu, and EDr. Results: The sample was 45 AYA patients with SCD between 13 and 22 years old. The mean TRAQ score for the overall patient sample was 3.67. Mean TRAQ scores did not significantly vary by sex or genotype but did significantly increase with age. TRAQ scores were lower in the SCD population than in other YSHCN. TRAQ scores did not correlate to EDu or EDr. Conclusions: AYA patients with SCD have lower transition readiness than other populations of YSHCN. The age of 18 may not be the most reliable attribute of readiness, though older patients do have higher readiness. The relationship between TRAQ scores, EDr, and EDu is not clear and requires further evaluation.