Dominica

If you're comfortable living in a country with fewer people than a mid-sized American suburb — the entire population is just under 72,000 — Dominica will sell you citizenship outright for $200,000 through its Citizenship by Investment Program, though most retirees use the country's more straightforward approach of simply obtaining residency through property ownership or showing proof of income. There's no formal retirement visa with a minimum income threshold like you'd find in Panama or Portugal, which means the path in is surprisingly flexible, but also means you're navigating a system built more for wealthy second-passport buyers than for traditional Social Security retirees. The cost of living runs lower than most Caribbean islands — you're looking at $1,500 to $2,500 monthly for a comfortable lifestyle — but the infrastructure reflects the population size and the country's vulnerability to hurricanes, which have devastated the island multiple times in recent years, most recently in 2017.

The healthcare system is limited to a single main hospital in Roseau and a handful of clinics, so any serious medical issue means evacuation to Martinique, Barbados, or back to the States, which you'll be funding yourself since Medicare doesn't work here. The internet exists but remains inconsistent outside the capital, the banking system is small and can be frustrating for Americans used to instant transfers and robust online platforms, and you're dealing with a genuinely remote location where Amazon doesn't deliver and replacement parts for anything take weeks. The upside is zero taxes on foreign income for new residents, a slower pace that actually feels slow rather than tourist-brochure slow, and the kind of tight-knit expat community that forms when there aren't many of you. This is for the retiree who wants genuine seclusion, doesn't need frequent medical care, and values tax advantages and Caribbean access over conveniences like same-day prescription refills or reliable high-speed internet.