This study compares the health conditions of domestic Caribbeans with those living in the United States to explore how national context and migration experiences might influence substance use (i.e., alcohol or drug) and other mental and physical health conditions. The study is based upon probability samples of non-institutionalized Caribbeans living in the United States (1621), Jamaica (1216) and Guyana (2068) 18 years of age and over. Employing descriptive statistics and multivariate analytic procedures, the results revealed that substance use and other physical health conditions and major depressive disorder and mania vary by national context, with higher rates among Caribbeans living in the United States. Context and generation status influenced health outcomes. Among first generation black Caribbeans, residing in the United States for a longer length of time is linked to poorer health outcomes. There were different socio-demographic correlates of health among at-home and abroad Caribbeans. The results of this study support the need for additional research to explain how national context, migratory experiences and generation status contribute to understanding substance use and mental disorders and physical health outcomes among Caribbean first generation and descendants within the United States, compared to those remaining in the Caribbean region.