Margaritaville and Other Best Places to Retire…

There is no shortage of lists and articles about the best places to retire.  These lists are fun.  However, they sometimes feel random and not all that practical or useful for figuring out where to spend this phase of your life.

For example, did you know that Jimmy Buffett is opening “Margaritaville” — a real retirement community in Florida?  But, do you really want to spend your golden years “wasted away” and “searchin for your lost shaker of salt?”  Maybe… Or, maybe not…

best places to retire

No matter how carefully compiled, it is unlikely that the authors of these lists really know what combination of attributes is really important to YOU and YOUR retirement.

Here are some ideas to help you assess where to live out this phase of your life.

Should I Stay or Go?

For some people, when to retire or what to do with their free time is the big decision.  For others, where to retire is the topic that defines their transition to retirement.

A recent survey by Bankrate showed that 50% of people ages 50 to 64 would consider relocating when they retire. However, that percentage drops to about 20% for people of retirement age — 65 and older.

It may be that more of us dream about moving than actually do.

The most important aspects of figuring out the best place to retire for you are:

  1. Knowing what you want out of life — What do you want to be doing, who do you want to do it with and in what type of environment?
  2. Figuring out how to use your financial resources to achieve what you want — The trickier part might be knowing what you can afford and for how long in retirement. Housing is usually your costliest expense and, for most retirees, it is their most valuable asset.  If you are short on retirement savings, downsizing and releasing some of your home equity can help you make ends meet — especially when combined with cutting your cost structures.

Is moving or staying put the best way to achieve both your lifestyle and financial goals for retirement?

Overall Affordability of Location

Some people get a bigger house when they retire, but most people (for lifestyle and budget purposes) downsize.  However, affordability of the best places to retire has many different aspects beyond the cost of the residence.

Taxes: State, local and sales taxes can vary tremendously.  Bankrate has a list of the most tax friendly states for retirees.

Cost of Living: If relocating, you will want to research the costs of what you buy or will be buying on a regular basis.  Don’t forget to consider differences in heating and cooling costs at your new location.  Want to keep your expenses low?  Try Kiplinger’s list of 23 Cheap Places to  Retire.

Affordability of Housing: Get Creative — Think Outside the Box

Maybe your ideal retirement destination is too expensive, have you considered thinking slightly outside the box regarding your housing?

Trailer Parks: Time Magazine recently featured a story about how trailer parks are “The Home of the Future” — particularly for retirees.  Charles M. Becker, an economist at Duke University, says: “Trailer parks can be thought of as gated communities for people who aren’t so wealthy.”  These communities often have tons of amenities — golf courses, swimming pools, tennis courts and more — that may be very appealing to retirees.

Tiny Homes: The tiny house phenomenon might be another way to make an expensive locale more affordable.

Housesharing: Getting a room mate is another way to increase affordability of certain locations.


Healthcare is another factor that you should consider when assessing the affordability of a location.  The costs of supplemental Medicare coverage will vary from state to state.

However, you also need to look at the availability of healthcare.  Some locations have more or better facilities.  Consider doctors, specialists, long term care services and hospitals.  Here are some tools to help you compare healthcare in different states:

Commonwealth Fund: This site has easy to use charting that lets you click on a state or county and see the ranking for how well healthcare is performing in that area.  In 2017, Vermont has the best overall ranking.

10 Best States for Medicare Advantage: Services that are available through Medicare Advantage vary greatly from state to state.  This may be a factor in your where to retire decision.  You can also check out which states have the best Medicare Part D plans.

Healthcare Abroad: If your best place to retire is abroad, you won’t be able to use Medicare.  Be sure to find out if you can opt into the local plan or what private insurance will cost.  International Medical Group offers plans.  Or, you may find that healthcare is much more affordable and you will be able to pay for services in cash.

Lifestyle Factors

Prioritizing which lifestyle factors are most important to you and which you can compromise on can be difficult.  Do you want maximum sunshine or be close to family?  Before searching for where to retire, brainstorm a list of what you want.  The more you know about how you want to be spending your time in retirement, the better chance you have of finding the best place.

If You Can Dream It, You Can Find It

As we said at the outset, lists of where to retire aren’t all that useful, but they do prove that if you can dream it, it is probably true.  Just look at a few of these retirement options for inspiration:

Quirky Retirement Locales:  Do you consider yourself free spirited?  Try AARP’s list of quirky places to retire.

Vroom: Lake Weir Living in Florida specializes in homes with unique garages for retirees who love motorcycles, RVs or classic cars.

Surfs Up?: Here are the best surf towns in America and abroad.

Want to Tee Off?: Research the best value golf courses in America.

Long Life: Why not retire to one of the “Blue Zones” — places where people live the longest…

Best Places to Retire Calculators

Once you have a good idea of what attributes the best place to retire would have for you, you could start using one of the many best places to retire calculators.  These tools will take you well beyond general lists and help you find the best place for YOU…

Best Place to Retire: This site offers a calculator that asks 12 questions to help you find the best place for you to retire.  Activities and amenities are well covered in this search. The results are nice in that they give you a lengthy list of options to compare.

Sperling’s Best Places: The questions in this calculator include taxes and cost of living and the quiz is quick and easy, but you are only given one result.

Thinking about retiring abroad?  Try these calculators:

TheEarthAwaits:   If you have ever dreamed of living abroad, this is an extraordinary site.  There is so much information about so many different destinations.

ExpatInfoDesk: The Expat Info Desk is owned and run by a team of expatriates. Each one of them has successfully relocated to cities throughout the world including Russia, Ukraine, Poland, South Africa, China, USA and India.  The site offers articles, guides and a forum.  The concept here is good, but it is unclear how active the user base is.  You might be better off visiting a travel web site like TripAdvisor that has so many users.

NewRetirement Planner

Do it yourself retirement planning: easy, comprehensive, reliable

NewRetirement Planner

Take financial wellness into your own hands and do it yourself retirement planning: easy, comprehensive, reliable.

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