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Don’t Forget These 5 Things When Choosing a Place to Retire

Category: Best Retirement Towns and States

September 15, 2021 – Members in a recent Topretirements poll gave us their number 1 considerations for choosing a place to retire. Atop the list by a large margin was climate, followed by affordability, being near friends and family, and good medical.  Much further down the list were taxes and political environment.

These are all important things to think about when choosing a place to retire. But there are other, less obvious considerations that are even more critical. Here are 5 overlooked considerations that we think deserve special attention.

  1. Do you really know the area where you about to relocate?

“Rose”, who retired to Myrtle Beach (SC), listed a perfect example of this situation in our recent poll: “Never retire where you like to visit. There are so many tourists and so much traffic it is unbearable. There is very little here that I was looking for, such as classes and like minded people.” 

So many people have written over the years expressing remorse about not renting in a community before deciding to buy. “If only we had known!” is a familiar refrain. Only by living in a place for an extended time can you get a good picture of what it is really like to live there. By putting a toe in the water you also find out the best places to live in that area, as well as those to be avoided. You also might find out that the grass isn’t necessarily greener.

2. Will you be happy if you are far away from your family and friends?

Families, grandchildren, and friends are powerful connections. Many people find that moving long distance, especially retiring abroad, creates too much separation. Many experienced this early through pandemic-caused isolation. A better choice, if separation will be too much, might be to choose life as a seasonal snowbird.

Disconnects between partners is another issue when choosing a place to retire. One might be an adventurer, and the other could be a homebody. One likes warm weather, the other loves winter.  Finding out these differences after you relocate can be painful and disruptive.

On the opposite side, many people move to be near their adult children, only to see the kids get transferred, or to resent being the default baby sitters.

3. Will you be comfortable with the political environment in your new location?

Unfortunately, this issue seems to be increasingly important in our now very divided society. Progressives moving to a conservative state or town might find themselves increasingly uncomfortable, and the same goes for conservatives migrating to a blue state. Fortunately, even the most dyed in the wool states have towns and areas that don’t fit the stereotype. Huge numbers of northern retirees are moving to southern states anyway, so how this plays out is unknown.

4. Do you know what kind of community you want to live in?

Most people entering retirement really don’t have a good understanding of what their community options are.  Just some of the community choices include 55+, active adult, co-housing, independent living, new urban, multi-generational, college town – or living in a city or traditional neighborhood. Each has its advantages and disadvantages, and until you have explored them you won’t know which is right for you. The best way is to explore when on vacation, visit  friends and family, use short term rentals, and take advantage of the “Stay and Play” packages offered by many developments. 

5. Will the medical situation and other factors allow you to live there for the rest of your life?

One of the best pieces of advice we ever heard (and rarely acted on) is to plan on retiring to an area where you can live the rest of your life. To do that requires weighing several complicated factors. For example, are medical resources close and sophisticated enough to handle any health issues that emerge down the road? 

Living high in the mountains or way off at the beach might not be convenient when you have to drive for hours to see your specialist. Is there an assisted living or CCRC (Continuing Care Retirement Community) nearby, or will you have to make a big move when your faculties decline. Abandoning the church, friends, doctors, etc. that you have come to depend on can be very difficult if you are lucky enough to live into your 80s or 90s.

Even climate change can come into play, as “Tim” commented recently: “Having lived in Northern California and Pacific Northwest for a long time, I am turning into a climate change refugee. All the lovely things that have kept me here are so much harder to enjoy when it’s smokey almost all the time.”

Bottom line:

There are plenty of good reasons for choosing a place to retire. Some aren’t quite as obvious as others, and although these might require a little planing and consideration, investing a little time in them can make a huge payoff in finding that perfect place to retire.

Comments? What factors, if any, did you overlook when you considered where to retire? Did all your plans work out as you expected, or where there some miscues. Please share your experiences, no matter where you are in your retirement search, in the Comments section below.

Posted by Admin on September 14th, 2021


  1. Over the last 18 years, I have worked with a few hundred couples searching for retirement locations, almost all of them in the Southeast U.S. Only a few of my clients did not address the “5 Things” TR suggests you not forget during a search for a home. “Rose” suggests you not move to a place you like to visit because the traffic and tourists will somehow bother you more when you live there permanently. One wonders if Rose paid any attention to her surroundings while she was a tourist. For many people, traffic is more annoying when on vacation…As for worries about being too far from family and friends, that is a decision that can be thought through before you decide to relocate — and can be neutralized by relocating near a good airport or interstate highway if you do move away. If the pull of family and friends is strong, maybe you downsize and stay pretty much where you are. At this point in our lives, age is supposed to confer wisdom. Surely we can figure this out before we relocate…You can pretty much figure out the political climate in areas you target by checking Presidential vote totals for 2016 and 2020. They are all readily available by county and city on the Internet. This will not guarantee that, within the gates of any one community, you won’t run into those who want to shove their opinions in your face — just like in the home town you are leaving. No one of the 150 or so communities I have visited comprise a single political party or mode of thought. You will always find people who think as you do, and others who don’t. You will learn to deal with it, even if it is annoying…The advice to take advantage of “Stay & Play” packages (also known as “Discovery Packages”) is excellent. You can learn a lot during two or three days stay (and at a nice discount) IF you ask all the questions that are on your mind. Most communities will match you with “ambassadors,” a resident couple used to working with prospects. They will almost always answer your questions directly and honestly; if you sense they aren’t, then consider moving on to explore another community for your permanent retirement location…Consideration of medical facilities nearby depends, largely, on your health profile. If you or your spouse have a history of heart problems or require occasional treatment for recurring cancer, you aren’t going to move two hours or more from qualified medical centers. If, on the other hand, you are a healthy 60 something, you might decide to forego proximity to medical care for the first part of your retirement. But, by all means, decide your preference and then filter out areas and communities that don’t measure up. Indeed, that is how you should treat all the most important requirements in your search, including those not on the list above.

    Editor’s Comment: Thanks Larry, this is great input!

    by Larry — September 15, 2021

  2. Another factor to consider for those of a particular faith is will there be a congregation nearby. In the South, you may not have a place of worship you are familiar with, especially if you are in a more rural area. You may have to be close to a larger city to find denominations that are common in the North or Midwest.

    by LS — September 15, 2021

  3. Great summary ! Also the cost of living, tax, climate change impacts

    by Ron — September 15, 2021

  4. I always get ideas from your posts and comments. Have you done a writeup up on “Discovery Packages”? With so many communities it would save time to zero in on a few that offer the tours and the experiences of someone who went. Carol

    Editor’s comment: What a great idea! We’ll get on it. In the meantime, it would be very helpful if people who have been on these stay and play packages (or other site tours) chime in with their experiences. Thanks

    by carol — September 15, 2021

  5. I just want to add a comment that we took advantage of two Stay and Play packages several years ago when we were seriously considering moving to Virginia or North Carolina. The communities have both sold out since then, and although we did not buy, we enjoyed our stays. The homes for our two-night stays were very nice of course, as were the agents we dealt with. With each community were shown around, and invited to enjoy all of the amenities, Other than that we were left alone, no pressure to buy a homesite or sign a contract. It was mainly the locations that we decided was not for us. Our Stay and Play experiences were both informative and helpful.

    by Jemmie — September 18, 2021

  6. Jemmie, what was it about the locations that were not for you? In hindsight, do you think more research about those locations prior to booking the Stay & Play might have saved you time? One common mistake made by many couples I work with is that they surf the net for communities that match their preferences — and ignore where they are located. The hierarchy of decision making about a place to live should always start with topography — coast, mountains, lake or somewhere else inland. Once a couple agrees on topography, the next decision is the specific area. If, for example, the decision is mountains, personal issues and preferences should guide consideration of the area. If medical issues are involved or you want to be near good restaurants and other services, you might choose a community near a full-service city like Asheville or Greenville. If not, there are plenty of communities far from traffic and pollution. Choosing a handful of areas to explore initially is a good idea; choosing communities to explore without regard to their locations could make for a long search.

    by Larry — September 19, 2021

  7. Larry, all excellent points. We did choose the Stay and Play communities while we were renting an apartment for 6-months in Raleigh and explored a lot of towns from there. One of the communities was in Wilmington, NC and the other was in Fredericksburg VA. (Two of our kids were in VA at the time and both have moved to other states since). We were more interested in the cities we visited than the communities, so I agree with you, it’s more about location and what is offered outside of the community’s gates. Another thing we learned along the way was that although retiring near good friends did at first appeal to us, we found their perfect retirement spot was not what we had in mind for ours.

    by Jemmie — September 19, 2021

  8. Jemmie, that last point is such a good one: No matter how close you may be to friends, their preferences and requirements for retirement living could very well be miles apart from your own.

    by Larry — September 19, 2021

  9. Jemmie,
    Fredericksburg, VA is on our radar and I would appreciate your views on your visit there. If you would not mind sharing what your impressions were when you visited, I would greatly appreciate your input.
    Thanks very much, any information is helpful in this huge decision!!

    by Sally — September 20, 2021

  10. Sally we enjoyed Fredericksburg during our short visit there, I would not discourage you from checking it out. The town is historic and a tourist destination, and with its close proximity to Washington D.C. there was a lot of traffic. We would be going to visit our home in Pennsylvania at least one a month and it wasn’t a pleasant drive from Fredericksburg so that is why we had to cross it off of our list.

    by Jemmie — September 20, 2021

  11. Sally,

    Check out the below link with top communities in VA (especially the 2 in Stafford and Spotsylvania). Regards, Danno

    Editor Comment: For reviews of over 30 towns and almost 100 communities, check out the Topretirements Directory for Virginia.

    by Danno — September 21, 2021

  12. Jemmie and Danno,
    Thanks to both of you for your information. I appreciate hearing from your experiences. All the info we can share with each other is extremely helpful, but personal observations can make one think about something we might otherwise miss. Many, many thanks for tips on Virginia from all, it really is the place I want to retire, just hard to narrow down exactly where!!

    by Sally — September 21, 2021

  13. Sally, Virginia, like NC, has vastly different communities in very different parts of the state. You can literally apply all the variances from around the US to these two states. Fredericksburg is nice, but many communities around DC share most of the advantages (and disadvantages) and most are quite different in many ways. You can also go farther out from DC possibly as far as Richmond or even Roanoke and find commonalities in very different places.

    We have spent most of our lives in NC, but also lived 10 years in VA– both the remote western mountains and northern VA 30 minutes from Fredericksburg (Bealeton while working in DC). We had great difficulty trying to decide on moving back to NC because it was just not that different.

    So expand your view, understand what you actually are looking for in retirement and tour around as much as you can.

    by RichPB — September 21, 2021

  14. RichPB,
    Thank you for your input. I am familiar with the vast differences and similarities in the different areas of VA, being born and growing up all over the state. The mountains are calling to me and that is why I am trying to hone in on maybe the northern areas. We have already looked in Richmond, I know that Roanoke is a nice place, my sister has lived there for most of her life. Other family members live in Blacksburg area. Those areas I have kind of ruled out for many reasons. So, now we are planning a trip in early November to Charlottesville, Fredericksburg and possibly Winchester to just explore. Sometimes this can be overwhelming because of all the wonderful possibilities! That is why I am so glad when the folks here can contribute some real life experiences in their travels. Please let me know if you have further thoughts on the areas I have mentioned, I truly appreciate the time you folks spend helping me!!

    by Sally — September 22, 2021

  15. Sally, Below are our reviews of the cities you are considering in Virginia, which may have already read, it appears you know the state well! After your visit, you can add a comment at the end of each review to give us your thoughts. Thanks, and have fun exploring.

    by Jane at Topretirements — September 22, 2021

  16. Sally, I get it now. VA calls to you just as NC called to us as it was “home”. I think many people looking for a retirement place may fail to understand how strong that call can be.

    by RichPB — September 22, 2021

  17. Sally, you have lived all over the state of Virginia and clearly know it well. You have decided you want to live in the mountains. You have made numerous visits across a state that you already know well. In terms of knowledge and preferences, you are way ahead of most who are looking for a retirement location. What is stopping you from making a decision? You will never know you have chosen the “perfect” place until you have lived there for a while. Choosing a “good” place is a great start.

    by Larry — September 23, 2021

  18. Larry,
    It’s the age old adage, afraid of making a mistake. If it was just me, no problem but I also am considering my husband. He keeps saying “I can build my shop anywhere”. He is quite an accomplished woodworker and that is a major part of our decision making, his ability to have an adequate shop space. And also, I am the one driving this move to VA because I want to go “home”. It will be taking us away from our only child and only grandson. We have moved all over the country with work and had limited choice. This move is for me. It is a lot for me to contend with and that is why I am trying to make it the perfect move. I know, there is no perfect place, but you can see that so many factors are weighing on this that make it quite complicated. Gosh you guys, I should send you all therapy fees for listening to me! Again, I cannot thank you enough for all your help!! Thanks to Jane for the specific info as well!

    by Sally — September 23, 2021

  19. Just a little note of encouragement for those of you who feel the “call” and are motivated to pick up and go! We did just that – left our kids and grandkids behind – even though they had already followed their work. We just went farther. Having lived all over – we too felt this was “our time” and we finally got to choose where we wanted to go. We landed in Maine – just outside of Portland – with TONS of stuff to do, great medical care and cooler weather. WE love it! So as not to be a burden as we age out, we’re touring various Retirement Communities (CCRC) and are on two wait-lists. This way no one HAS to get on a plane every time we get a cold. It can be done! Do I miss them? Yes, but I am so happy to be in my dream spot.

    by HEF — September 23, 2021

  20. HEF,
    Thanks for the encouragement. Statistics are helpful, but hearing from you folks with your actual experiences makes the decision a lot easier. I know we can do it, and we will be happy wherever we land if we have put in the time to educate and be honest with ourselves about priorities. Other peoples success stories are so helpful! That is what I enjoy the most from this blog, you actually get a mix of both statistics and real lived journeys. Many thanks to everyone who has participated in this string.

    by Sally — September 24, 2021

  21. Sally – one thing to help with moving to a new place, is to reach out online ahead of time!! I do a lot of needlework, knitting, etc and I looked up people on several websites that cater to those things. I reached out and chatted with several people and found a number of groups in the area we were shopping. We made a fact-finding-trip up in 2015 with a list of questions, people to meet and places to visit (like the supermarket to compare prices and a Medical Gym). Knowing we no longer had children to pave the way – once we made the move, we had people we “knew” (from online), already in place. I joined 3 groups, husband got involved with several and we made friends faster this time than we ever had!

    We also found a Realtor who had a history of working with Retirees. (referred from someone else who had retired to Maine) We met with her in 2015 and didn’t make the move until Dec.2017. She was patient until we were ready and found us the perfect location. She was able to hook us up with a terrific local guy to move us, contractors to do the renovation work we wanted and had a wonderful network of various folks to help us out. Just keep asking questions!

    by HEF — September 24, 2021

  22. HEF,
    You really could write a book about preparing for a move in retirement! You are a wealth of information and it is really appreciated. I sew, quilt, etc, so will look into stuff like that prior to our visit. I am narrowing down my search for our trip to Fredericksburg, VA, already looked into grocery stores, am spoiled by our Publix but understand Wegmans is really good too. Next will be Medical facilities. Already checked out the local Level II Trauma center as the best available in that area, that is a little disappointing, was looking for Level I. Thanks again for all your advise. Good thing about getting older, we realize just how much people can help you, if you just ask!

    by Sally — September 25, 2021

  23. Sally:

    Wegmans is far above Publix as far as grocery stores–you will not be disappointed. A new location is opening within a few months near my home, and I am very excited about it. I live in DC, not far from the Maryland state line

    by Jennifer — September 26, 2021

  24. You are so right about Wegmans Jennifer I love that store. Can I ask what community you live in in DC?

    by Virginia — September 26, 2021

  25. Hi Virginia:

    I am in Cathedral Heights and Wesley Heights–both claim our area. Are you also in DC?

    by Jennifer Lee — September 27, 2021

  26. Jennifer I’m hoping to relocate to a 55 plus somewhere between Baltimore & DC to be closer to family. All suggestions would be welcome.

    by Virginia — September 27, 2021

  27. Another costly tax to remember when considering a move is personal property tax! In states like South Carolina automobile tax is based on your cars value. A new car or truck can cost you easily 600 to 1000 dollar’s annually!
    Also watch sales tax it varies county by county and can add up to 10% to your grocery and other purchases

    by Ron — September 28, 2021

  28. HEF,
    I read your posts about moving to Maine with great interest. Maine is one of the states on my possible “retire to” list, but I’m still several years away. I also have lots of questions and wonder if one can PM you. And, is there any way to find out which realtor you worked with in Maine? He or she sounds fantastic. Thanks for any information you might offer!

    by StephanIe — September 29, 2021

  29. You may want to add “Climate Change” as a consideration when choosing a place to retire. My wife and I thought we had our dream retirement all planned out in southern Oregon. Three straight years of wildfires made us re-think our strategy. Thought about the southwest, but after some research on the water situation and how little could be available when I’m in my 70’s, no thank you. The military transplanted us to a wonderful, but snowy (much more than we prefer) location some 30 years ago. We still have lots of family and friends back home, so that’s where we are headed.

    by Brian — October 12, 2021

  30. Stephanie and Brian, your comments about a retirement in states with cold winter weather illustrates a coming shift in migration patterns driven, in part, by climate change but also by other factors. With wildfires a constant reality in the west and northwest, with increasing heat of summer in the southwest and south, with rising sea waters in all coastal areas everywhere, where is a couple supposed to live out their days comfortably and safely? The answer, more and more, will become New England and the upper Midwest for those who cannot afford two homes which, I suspect, is most of us. I had a hint of this while in Vermont in September where my wife and I spent a month relaxing beside Lake Champlain and visiting our daughter and her family in nearby St. Albans, 15 minutes from the Canadian border. I played a lot of golf in September, and during one round, I followed seven foursomes of couples — all of them winter residents of Florida and summer residents of Vermont. The club’s GM later told me they have 50 Florida members. Yes, that is an anecdote, but given increasingly unpredictable weather elsewhere and the “harmony” of life in Vermont — Republican governor, Democrat legislature, the granola and gun-bearing crowds getting along, best performance in the nation on Covid — more and more retirees are likely to consider the higher cost of living and need for a ski jacket in winter as small prices to pay. In other words, “The North Shall Rise Again.”

    by Larry — October 13, 2021

  31. Larry:

    I spent a good deal of time in Vermont and New Hampshire and I love both states. Maine too is a potential contender, but I love the mountains–in the summer give me a freshwater lake! In the winter, I can fly to a warmer climate if I wish, however New Englanders know how to treat the roads, and if one locates in a walkable location, it would be a non-issue for me since I would probably give up working altogether by then. I can fly to warmer weather in January or February or better yet take the train. I know I cannot take 24/7 humidity and heat–Florida has never been on my list. I hate and fear snakes anyway.

    by Jennifer — October 13, 2021

  32. Jennifer, we are definitely on the same page. If I could afford it, I would find an apartment in Burlington, VT, with a view of Lake Champlain and a short walk to Church Street, the pedestrian mall with great shops, restaurants and cafes. Barring that, a small town with a tavern with good food and a cafe at its center. I drove through Montgomery, VT, two weeks ago and that seemed to check all the boxes. Good luck in your search.

    by Larry — October 13, 2021


    by Eva — October 13, 2021

  34. Finding the best place for you takes time and effort. There are no short cuts. We started looking many years before retirement was on our horizon. We did multiple “stay and plays” and checked out towns in areas that we enjoyed vacationing in. We created a checklist that included all that we felt was important. We returned to our favorite places and stayed again, during different seasons and spent time to talk to residents about their communities.
    Fast forward, we ended up in Texas after living in the northeast our entire lives. We rented a house for six months before purchasing our home. We love our community and feel very fortunate to have found wonderful friends, health care, culture that matches the majority of our desires.
    There are so many considerations that come into play when making the decision to pull up stakes and move to the unknown. My recommendation is be brave! Visit, chat with others and try out before you buy. Don’t let preconceived ideas about politics be a deterrent. Red and blue should not bother you. People are people no matter where you live.
    My advice, enjoy the time we have here on earth. It’s too darn short!

    by Pezz — October 15, 2021

  35. Please forgive me, but I am tempted to say “Pezz, Dispenser of Good Advice.” (Baby Boomer reference there.) For almost 17 years, I have been working with couples searching for their dream community (in my case, golf communities). The process that Pezz describes may not be the quickest but the few of my clients who had the means to travel to all the places on their list and to rent before they bought all wound up gloriously happy with their ultimate choices. Of course, there are risks to an elongated process; some couples find a place that checks almost all their boxes early in their search and think their 100% community is out there somewhere. In that case, perfect is the enemy of good and their searches go on and on. (My first contact with some couples still searching was 10 years ago.). Also, if a couple started seriously looking three years ago for a home priced then at, say, $400,000, they will have to pay more than $500,000 today because the market has gone so nuts during the pandemic. Absolutely have a checklist you or both of you, if a couple, agree on and make sure you rank them in order of importance to you: Requirements at the top, preferences below. Figure out your geography requirements first; coastal, mountains, lake or inland with no water. (Big mistake, in my opinion, is to say “We like the coast and the mountains.” Pick one and focus.) Then check out the websites of communities and compare what they offer against your requirements. Any that don’t match up, strike them from consideration and move on. When you find some in an area that match all your requirements, visit them and see how they compare on the “preferences” list. Do that in an organized way and you are on your way to the happy retirement that Pezz described.

    by Larry — October 16, 2021

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