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Lifestyle & Travel

A Road Trip to Retirement

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Use your summer vacation to check out places where you might want to live.

As I eagerly await the time of life when I can do as I please—no more alarm clocks or time clocks to answer to— I'm practically giddy at the chance to find the right place to spend my later years. The stakes are high: Too few of us have enough money for retirement, so we might need to find a town we can afford not just for now but for decades to come—not to mention one that has (we hope) the amenities and features we need and love, from restaurants and culture to good weather and jobs if we do have to work. (Plenty of folks, of course, want to stay where they are as they get older, and others don’t want to move but must. So the hunt isn’t a pleasure for everyone, for sure.)

My fiancé and I are a handful of years away from his early retirement (I’m eight years younger so I still have quite a few more years left to work) so we’re beginning to think, 'Where do we want to live next (and maybe for good)?' That’s why we’ve decided to dedicate  part of our summer  to visiting cities we think we might want to call home down the road. By starting the process early and making it part of something fun we’d want to do anyway, we hope to find a perfect spot. But we’re also open to what happens; we realize that we may well come across a place we didn’t know anything about that just feels right.

Someplace New, Someplace Old

Next summer, our plans are to head north from Long Beach, California, where we live, to Oregon. We’ve long targeted Portland for our retirement, for its good restaurants and breweries, progressive politics, ample greenery and natural beauty, and relatively low cost of living (at least compared to Southern California).

But the truth is that I’ve only visited the City of Roses a few times, and Fred has never been there. So our plan for summer 2017 is to not only go to Portland, but also head to Ashland (rated a “Best Boomer Town,” in fact), Eugene, maybe Corvallis, and Bend, about which Fred has heard good things. In other words, we’ll do our research on all five towns, then hit the road to explore the state, perhaps even making it up to Seattle or east to Boise while we’re at it. Once we’ve decided on a spot that seems right and we’re closer to actually retiring, our hope is to rent a place there for a few months—getting a feel for a city over a couple of seasons at least—before making a move.

Also on our list is my hometown: Scottsdale, Arizona. The brutal summers notwithstanding, the low cost of living here is legendary, having attracted snowbirds and retirees for decades, along with lovely winters and early springs. included Apache Junction, a small suburb east of Phoenix, in its “25 Best Places to Retire 2016” list, and a list gave Mesa, another Phoenix suburb, its top honors as the best U.S. city for retirement, followed by Prescott at No. 3 and Tucson at No. 4. Flagstaff has also cropped up on past “best of” lists for retirees, too. Call me nostalgic (or just not very adventurous), but there is something appealing about moving to a place where I already know how to get around and also have family.

Of course, there’s no reason to play it so safe; you may want to cast a very wide net—even scoping out a cross-country adventure this summer, in which you hit multiple places based on research you’ve done or simply on locales that have caught your fancy. One especially good source for finding the right place to retire is the “Best Cities for Successful Aging Report,” put out by the Milken Institute in 2014. Unlike a lot of other reports, this analysis is founded on good data; it assessed 352 U.S metro areas, large and small, “based on how well they enable older people to fulfill their potential.”

What Makes a Great Place to Retire?

To figure out what makes a great future retirement spot for you, you can simply use the same criteria the Institute looked at and ask yourself how important each is to you and what, exactly, you’re looking for in a place to live. Here are the categories, as well as some sample questions to consider: 

  • Health and wellness (How accessible is health care? What about quality nursing care and assisted living facilities, when you do need them?)
  • Crime rate (Which areas have the highest and lowest rates?)
  • Weather (How important is good weather to you?)
  • Economic and job conditions (Are there likely to be jobs for you if you want to keep working or work part-time? How stable is the economy?)
  • Housing (How expensive is an apartment, condo, or house? What about property taxes and other expenses to keep up a home? Can you transition to assisted living easily?)
  • Transportation (Is there public transportation if you want to use it, or need it later? How much are fares?)
  • Social engagement (Will you be able to be part of a connected community? Are there opportunities for volunteering, learning, and recreation?)

It is a little scary not to know where we’ll end up—or if that place will, in fact, be where we’ll retire—but it’s also exciting to create this next chapter together and making it a road trip makes it seem less daunting and a whole lot more fun.

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