Contact Us: 781-705-6400

Where Should You Retire?

Being able to retire is a bit like being independently wealthy — you can live anywhere you choose. But where should you live if you have so much choice?

Of course, that level of freedom and financial security probably overstates matters for most people. Few retirees can afford a pied a terre in Manhattan or beachfront property in Manhattan Beach. But you may have several options if you’re no longer tied down to a place of employment. And you may have some cash available, especially if you’re able to exchange you’re home in a high-cost market like greater Boston for one in a lower-cost part of the country, or overseas for that matter.

There are a lot of considerations to take into account in making a decision, including:

  • What can you afford?
  • Will you want to or have to continue working part-time?
  • Do you want to be near friends and family?
  • What climate do you prefer? Related to this are issues of climate change. While you might like the warmth of Florida, it might be getting too warm for year-round living and seems increasingly susceptible to flooding.
  • Do you have any health issues that could affect where you must receive care?
  • What do you enjoy doing? Hiking, playing tennis (or pickle ball?), or going out to the theater?

Answers to these questions can help guide your decision making. So can a number of on-line services and lists that rate the best places to retire both in the United States and internationally. Here are a few of them:

Age Friendly uses a combination of user reviews and information from the World Health Organization’s Network of Age-Friendly Cities to provide information about the best locations in which to retire, as well where best to receive health care and to work in retirement. Perhaps because it is based in Massachusetts, the Commonwealth’s municipalities rank high as places to retire, with Waltham coming in first and Lowell second.

U.S. News

Just like it ranks colleges and universities, U.S. News compares 150 metropolitan areas as places to retire based on their job markets, housing costs, quality of life, and “desirability.” Based on their criteria, towns in Pennsylvania and Florida take 12 of the top 13 slots, starting with Lancaster and Harrisburg, Pennsylvania, and Pensacola, Florida. Pennsylvania appears to do very well on health care factors.The first town from another state to break into the list is Ann Arbor, Michigan at number 8. The first Massachusetts municipalities to make the list are Springfield and Worcester, ranked 32nd and 33rd, respectively. However, there is a lot of bunching at the top. Springfield and Worcester both receive overall scores of 7.0, not far below the overall scores for the top-ranked towns of 7.2.

Best Small Towns

If you would prefer to live in a rural area, Travel & Leisure magazine lists the 10 best small towns in which to retire, starting with Greer, South Carolina, Coolidge, Arizona, and Dillsboro, North Carolina. Some of these are very small. Dillsboro, for instance, has fewer than 300 residents.

Best by State

Kiplinger magazine picks the best town or city in which to retire for each state. For Massachusetts, it picks Pittsfield. It also ranks the states, with South Dakota ranked first and New York coming in last. Being a finance publication, Kiplinger seems to weight cost of living highly. Massachusetts comes in second to last.

Cost of Living

The Center for Social and Demographic Research on Aging at UMass Boston has created an on-line calculator, which it calls the Elder Index, of the cost of living throughout the United States. If you are considering more than one location, you can use the calculator to compare the cost of living in each. The calculator adjusts the results depending on whether you are single or part of a couple, whether you rent or own your home, and whether you are in good or poor health.

Leaving the Country

You may decide you’re better off retiring outside the United States, whether due to the lower cost of living in many places, a better climate, or simply your desire to experience another culture. The Natixis Global Retirement Index ranks the top 25 countries in which to retire, taking into account health, quality of life, material wellbeing and finances. Norway, Switzerland and Iceland take the top three slots. The United States comes in at the 18th best country in which to retire.

The problem with this list for Americans making decisions on where to retire is that it’s really a list of the best places to be from in retirement. While it may be great to be a Norwegian, Swiss or Icelandic retiree, they are probably cost-prohibitive as options for American retirees to relocate. Global Citizen Solutions, which assists people moving from one country to another, may have a more realistic list. It’s top three countries for American retirees are Portugal, Panama, and Costa Rica.

Other Resources

See other resources for choosing where to retire here.


Deciding where to live is difficult, probably more difficult if you can live just about anywhere — too much choice. The above resources, as well as others you can find on line, should help in making a decision, but two pieces of advice: First, look before you leap. Try out your retirement location for a month or a season before you commit. Second, think about your location both for your early retirement, when you’re likely to be in a good health, and for your older age when you’re more likely to need assistance. Will your new location work for both? If not, is that okay? We’ve seen many clients move to Florida as young retirees and then back to Massachusetts to be near family when they’ve needed assistance. That might be a fine plan, but it’s better if it’s a plan than the result of lack of planning.

Newsletter Sign Up

Contact Us

We’ve moved. But not far. Our new address is: 20 William Street, Suite 320, Wellesley, MA 02481

Contact Haley

Contact Steven

Contact Sarah Henry

Contact Michael

Contact Sarah Hartline

Contact Laura

Contact Patricia

Contact Jeffrey

Contact Harry