 There are certain people I tell they'd worry me to death, so I better know that I'm going to do it. Shifting to where you will be retired, this is from Money Wise. Top retirement destinations, Sarasota, Florida, Asheville, North Carolina, and Huntsville, Alabama, among the top cities for retirement, offering a mix of affordability, recreational opportunities, and health care facilities. And, of course, health care facilities, that is an important consideration. But it's not only about geographically where you will retire, but maybe what will be your dwelling.