Ahoy! Charting Your Course to a Perfect Retirement Destination

AdobeStock_464008213-300x191There is something very appealing and kind of romantic about sailing off into the sunset to enjoy the golden years of retirement in an idyllic setting. It is, perhaps, the pinnacle of the American Dream. 

However, selecting the perfect place to retire takes more than just dreaming. It’s a process of self-discovery, research, prioritization, due diligence, exploration, and careful planning. Which isn’t to say that it can’t also be fun. 

To help you get started, we’ve compiled a list of some of the key considerations that you’ll want to keep top of mind as you navigate through where you might want to live.

We’ve broken them down into four categories: Lifestyle, Family & Friends, Health & Safety, and Finances. We’ve listed these considerations in no particular order because they are all important. 


The Ingredients for a Life You Love

Imagine your perfect day. What are you doing? Who are you seeing? What’s the setting? Are you enjoying the vitality of an urban center, or relaxing in a pastoral country landscape? Are you curled up with a good book, or are you out on the town with friends, maybe taking in a theater show or concert? 

In other words, what are the things that you need to improve your quality of life?

Brainstorm about what you’d like to be doing, and what you need to make that dream a reality. How important is it that you have access to nature, an active cultural scene, upscale shopping, educational opportunities, volunteer organizations, etc.? 

AdobeStock_321809569-300x176Must-have Everyday Amenities

In addition to your perfect day, your retirement will also include lots of ordinary days. Think about the services and conveniences that you might take for granted where you live now.

Are you close to your favorite grocery chain or wholesale store? Is there a farmer’s market offering fresh, local produce in your neighborhood? Do you have access to public transportation? Is there a great library in your town? 


Are you all about sunshine and surf, or do you prefer the coziness of curling up by the fire during a snowstorm? What’s better—dry or humid? Is it important for you to experience all four seasons, or are you okay with the weather being pretty consistent all year round?

Think not only about the kind of weather you prefer now, but also what you might prefer a few years down the road. Snow might be appealing if you’re still hitting the slopes, but it might be less so as you get older, and don’t want to have to deal with driving in the stuff, or shoveling it.

Airport Location

If your dream retirement includes frequent travel, you’ll want to consider the location of the nearest airport. Is it close enough for an easy escape, or does just getting to your plane require its own itinerary and a day’s worth of effort? Airport location can also be an important factor if you’re planning on having friends and family visit.


Proximity to Kids and GrandkidsAdobeStock_273658951-300x200

How close is too close, and how far is too far? You may want to be closer so you can visit more or so you don’t feel bad if you sometimes need to ask for help.

On the other hand, you may want to avoid becoming the default babysitter. (Grandkids are great, but you don’t want to inadvertently sign up for a second career in child care.)

Opportunities for New Friendships

While moving to your dream retirement location is exciting and rewarding, it can also be bittersweet if you’re leaving close friends behind. But, if you choose the right kind of community, you may have the chance to forge new relationships.

What kinds of social opportunities are available? Does the location already have a retiree population? What about senior centers and clubs? Is there a calendar of local events where you might be able to meet people? Are there organizations related to your hobbies?

Diversity and Political Climate

Choosing a new home also means choosing new neighbors. Depending on where you are coming from, you may have enjoyed the benefits of living beside and with a wide variety of people who come from diverse backgrounds and bring unique value to your community. For example, do you prefer to live in a community composed mainly of people your own age, or would you rather have the opportunity to engage with young people and kids? 

Whatever your political views or level of political engagement, it’s also worth understanding the political environment of a place before you move there. Like death and taxes, politics are a mostly unavoidable topic, so it’s smart to assess your comfort level in that area.   


Basic Neighborhood Safety

One thing we all want is to feel safe and secure in our homes and neighborhoods. There are a number of sources that provide crime data. Some commercial sites include ones from LexisNexis and ADT. One of the most reliable sources, though slightly more difficult to navigate, is the FBI’s Crime Data Explorer

Hospital-300x236Quality Healthcare

Even if you’re in good health now, you’ll likely want to be at least somewhat close to a major medical center … just in case. And if you have specific conditions or disabilities that require specialized care, you’ll definitely want to make sure you land in a place that has fairly easy access to the doctors and other practitioners you need. 

Quality Assisted Living, Nursing Facilities, and other Senior Support Services

Part of choosing the right retirement location is being able to anticipate and plan for future needs. You may not need them now, but it’s a good idea to survey the area services related to assisted living, long-term care, and other senior services such as transportation, municipal support, and home care providers.

Climate and Natural Disasters

Thinking about the day-to-day weather is part of assessing the lifestyle possibilities of a location, but it’s also worthwhile to spend at least a few minutes considering a location’s climate and frequency of catastrophic weather events such as earthquakes, blizzards, hurricanes, tornadoes, and flooding. These should be considered not only in terms of basic safety, but also in terms of potential increased costs to insure your home and other property. You can do a quick check of climate risks on climatecheck.com


Cost of Living

From real estate prices to the expense of a night out on the town, a location’s cost of living provides an important reality check. Consider not only your basic living expenses (mortgage or rent, utilities, groceries, gas, etc.), but also what you expect to spend on entertainment. And, don’t forget to factor things like insurance and healthcare into the mix. There are a number of online cost-of-living calculators (like this one) that you can use to get started.


Just because a location has a lower tax rate or no income tax doesn’t mean that it’s automatically a better option. For instance, a state that doesn’t have income tax may initially appear to be a better bet. However, another state that has a moderately high income tax, but doesn’t tax Social Security in retirement might actually be a better deal.

Bottom line: Be sure to speak with an expert about how different tax rates might impact your finances. (If you want to do a little homework first, Kiplinger magazine offers a state-by-state guide to taxes on retirees).

Local Prosperity Trends

You may not need to retire in a booming metropolis, but you will want a location that offers some economic stability. And while no one has a crystal ball, there are some indicators that can give you a sense of whether an area is likely to grow or slip into decline.

For instance, the prevalence of major employers in strong and forward-looking industries is a positive sign, while an overabundance of reliance on industries that have peaked is not. You might also look into population growth, building trends, and retail tenancy. In general, areas around major urban centers and universities tend to maintain their prosperity over the long term.

Ready to start planning the next chapter of your life?

Getting started is easy. A great resource for basic demographic and other data on different locations is bestplaces.net. And a simple online search will provide you with a wealth of “best places to retire” articles, like these from Kiplinger, Travel & Leisure (in case you’re thinking of going international), Forbes, or Money

pros-and-cons-300x200Once you have a list of places, it’s time to start your research by digging a little deeper into all the considerations with a pros-and-cons list to help you whittle your list down to a more manageable size. 

From there, it’s time to hit the road and test drive your top picks. This might be in the form of a shorter, vacation-length visit, short-term rental, or a more prolonged stay. This will give you a chance to experience the place like a local, and maybe even get to know some of the locals. 

There’s a lot to consider when trying to select a retirement location, but the process can actually be a lot of fun.

Ultimately, you will make your decision based on some combination of logic and emotion. At the end of the day, you are the only one who can find the perfect balance between those two influences, and make a decision about where to have your happily ever after. Enjoy the process and may you have fair winds and following seas along your way to discovery!

Related Posts:

Making the Right Move: Understanding the 6 Senior Living Options

Senior Living Options: Cracking the Code

Retirees Cashing In on the Sharing Economy

Positive Aging: Why It Matters and Where to Start

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