What is the cheapest Caribbean island to retire to?

Among the popular US-retiree Caribbean destinations, the cheaper end runs Dominican Republic at roughly $1,450 and Trinidad at $1,875 per person per month on a moderate lifestyle, then Aruba at $2,700, Curaçao at $3,100, the Bahamas at $3,450, US Virgin Islands locations (St Croix $3,500 to $3,975), Cayman $3,800, and Bermuda well above $4,000. “Cheapest” usually means trading off infrastructure, healthcare quality, visa friction, and English use. Aruba and Curaçao tend to be the practical balance point for many US retirees: both materially cheaper than Cayman or the USVI, with clear retirement-permit routes, dollar-pegged currency in Aruba and Curaçao’s guilder on a stable dollar peg, and reasonable healthcare in Oranjestad and Willemstad. Cheaper islands compromise more on those factors. For the full Curaçao picture, see our Curaçao cost of living page.