Abstract Background Retirement migration from northern countries to southern countries is increasing in both Europe and North America, and retiree experiences will impact future migration and health services utilization. We therefore sought to describe the healthcare experiences and perceptions of retired U.S. citizens currently living in Mexico and Panama. Methods 46 retired U.S. citizens (23 per country) who had been hospitalized (61%) or had a chronic health condition (78%) in two regions per country with large communities of retired U.S. citizens were identified. Detailed semi-structured interviews were conducted to explore experiences with, attitudes toward, and costs of healthcare. Interviews were analyzed using quantitative and qualitative methods. Results Respondents averaged 68–70 years old, were well educated, had few physical dependencies, and had moderate incomes. They praised physician services as more personalized than in the U.S. and home care as inexpensive and widely available, expressed favorable opinions regarding outpatient and dental care, gave mixed ratings on hospital services, and expressed concerns about emergency services. Numerous concerns about health insurance were expressed, including the unavailability of Medicare and reductions in Tricare. Payment concerns and lack of data on local health providers made deciding where to obtain services challenging. Conclusions Retirees living abroad report dilemmas regarding healthcare choices, insurance availability, and quality of care. As this population segment grows, pressure will increase for policy and business solutions to existing medical care challenges.