In 2026, the Dominican Republic is widely considered the cheapest Caribbean country for expats to live a comfortable, "Western-style" life. While Haiti is technically cheaper in terms of raw costs, it is often excluded from expat lists due to ongoing political and safety concerns. In the Dominican Republic, a single person can live modestly on a budget of $1,200 to $1,500 per month, while a couple can live well for under $2,500, including rent in popular areas like Las Terrenas or Puerto Plata. Other affordable options include Grenada and Dominica, which are part of the "Windward Islands" and offer a lower cost of living compared to high-end hubs like the Cayman Islands or the Bahamas. For those seeking "Citizenship by Investment" programs, Dominica remains one of the most accessible and cost-effective entry points into the Caribbean. The affordability of these nations is driven by lower real estate prices, cheaper local produce, and a more "local" economy compared to the tourist-centric, import-heavy islands of the North.