Health progress in the 1960s and 1970s placed Cuba at the vanguard of longevity in Latin America and the Caribbean. This success has often been attributed to equity of access to the health care system and its cost-effectiveness in the country. Cuba also has a small gender gap in life expectancy. In this study, we examined how this pattern is reflected in the gender differences in health among the population aged 60+ in Havana. We compared gender differences in health in samples drawn from Havana, Mexico City, and the US Hispanic population: three geographic settings with very different political, health care, and social systems. The data come from the Survey on Health, Well-Being, and Aging in Latin America and the Caribbean and the 2000 Health and Retirement Study. Age-adjusted prevalence and logistic regressions were estimated for poor self-rated health, limitations on activities of daily living, depression, and mobility limitations. While an absolute female disadvantage in health was apparent in all three populations, the relative gender differences were inconsistent across all four health domains. Gender differences were most pronounced in Havana, even after adjusting for age, socio-economic status, family characteristics, and smoking behaviour. Despite having higher overall life expectancy and more equitable and universal access to primary care and preventive medicine, women in Havana appear to have a larger burden of ill health than women in less equitable societies. The study provides indirect evidence that Cuba faces challenges in combating the health threats posed by chronic diseases and other diseases and conditions common among the population aged 60+.