Methodology To find MONEY’s Best Places to Retire, we looked only at places with populations above 50,000…, collected about 47,500 different data points…, considered data on each place’s economic health, cost of living, health care, safety, diversity, quality of life, and amenities. To pick the retirement destinations noted here, we put the greatest weight on health and safety, cost of living, housing and economic factors, as well as the percentage of residents age 50 or above.