Objectives: This research article tests Litwak and Longino’s first-move hypothesis by taking chain migration into account. Besides adding to the body of literature examining later-life migration and disability using large-scale and current data, my scholarly contribution is noteworthy because this analysis is among the handful which accounts for the influence of historical flows. Methods: Using the American Community Survey (ACS) from 2006 to 2007, the author employs multinomial logit (MNL) to test the likelihood of migrating within the state, outside the state, Florida, or Arizona based on mobility difficulty, personal care limitation, physical limitation, and cognitive difficulty. In addition, the author constructs chain migration variables from Census inflow–outflow tabulations and Internal Revenue Service (IRS) county-to-county migration files. Results: The descriptive statistics and MNL estimates show the probability of migration is greater for individuals with fewer disabilities (i.e., better health), even after controlling for long-standing patterns of established inflows. More specifically, migration to Florida is greater for those without physical limitations and cognitive difficulties, married, with greater income, and higher education levels. Interestingly, the author discovers migration to Florida remains high despite disability status, if and only if the individual comes from an area of chain migration. Discussion: Given the first wave of the baby boom generation having reached retirement age in 2011 and a steady increase in these numbers for the upcoming few decades, examining this group’s geographic mobility serves a practical purpose for economic growth. Several independent studies show migrating retirees boost local businesses and provide increased sales tax revenue. However, states must balance this financial gain with increased use of health services, roadways, and community resources.