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Why Your Best Place to Retire Might be… 2 Places

Category: Best Retirement Towns and States

Updated December 20, 2016 (Originally posted April 18, 2011)

Like most of our members you are probably working on finding your best place to retire. Will your retirement destination will be where you live now, in the same region, or far away – there are so many possibilities! This article is dedicated to a different idea – that your best place to retire might be 2 places. You might also be interested in this companion article for ideas on dual places to live: “Best Places to Retire: Our Ideal Snowbird Pairings“.

On the Plus Side – Avoiding Compromises
Perhaps the best reason to consider retiring in 2 places is that it helps avoid compromises. Let’s say you hate cold winters and/or hot summers. That’s easy, keeping a home up north for the summers while living in Florida, Hawaii, Mexico, or California during the winters will let you live year round where the weather is always nice. If you can swing it (more about that later), that might be better than a compromise solution like moving to the Carolinas full time where the winters are still chilly and the summers pretty darn hot. You also get the advantage that you can probably stay in contact and hang around with your old friends for half the year.

The Best of Both, and Variety
Living in two places means you don’t have to settle for one kind of lifestyle. For example, you might want the activities of an active adult community, but don’t necessarily want to be in that in kind of environment all year long. Or, you might find that living in a house in one location and an apartment in another offers an interesting variety. Perhaps you would like to live part of the time in an urban environment as a change from the suburbs or small town. Two (or even more places) can help you enjoy a wide and enriching array of lifestyles. Most of the retirees we know of report that living in two different places adds a great deal to their lives – new friends, experiences, and a break from the routine.

The lighthouse in Chatham (Cape Cod), Mass. A great place for seasonal retirement

Different Strategies
There are no rules about the different places you can live in, or the lifestyle you have to choose. Your choice could be as simple as participating in a home exchange program like, which lets you swap homes with people around the globe. Many people find these invigorating – once a year or more. You might own a home in one state, and rent in another. A big advantage of renting is that you have no strings attached. One winter you get to sample Hawaii, the next year Arizona. Maybe you keep doing that for years, or perhaps you find the perfect location and then always go there.

Coping with the Cost
So many retirees are worried about retiring at all, let alone having the money to live in 2 different places. Yet creativity can come to your rescue. You can start by selling your big house in the suburbs. Downsizing will increase your available retirement nest egg while it alos reduces your costs.

You don’t have to own 2 places – you might rent one or even both. If money is a serious issue you can even reverse the seasons (go south for the summer and north for the winter). Although a radical thing to to do, you can get a rent for a fraction of in-season rates, while renting your opposite home out at high-season rates.

If you travel to the right place you might be able to get seasonal employment to help cover your costs.

You can be creative in many other ways. We know a surprisingly large number of retirees (particularly former military) who winter down south or summer out west in a large RV. The RV lifestyle, year-round or seasonal, can be inexpensive and fun too. Many people live on a boat for part of the year.

Spending a season in an international country can be another way to stretch your budget. Numerous communities in Mexico and South America offer a very low cost of living as well as a safe setting for expatriates.

On the Down Side
The 2 home lifestyle is definitely not for everybody. Moving away permanently from where you live now means saying goodbye to most of your friends and ties to the community. The costs for owning 2 homes will be higher than 1 – there is no escaping dual costs for insurance, utilities, taxes, and maintenance (although they can be mitigated by renting one or both out when you are not there). The hassle factor is not insignificant either. You have to worry about two places instead of one, which means someone to watch over your property and arrange for maintenance. Twice a year (or more), you’ll have to close down one place, pack up, and move to another. That involves many chores, and once in the new spot, you will inevitably find that something you really need is 1000 miles away. As your editor’s dear wife says, “You are always missing one place when you are in the other.”

Another factor is the interruption to daily life. If you are an active volunteer with a key role to play in an organization, that will be very hard to maintain if you are away for months at a time. Likewise it is hard to get involved in a new community if your presence is not continuous. This drawback, if not addressed, can make you feel rootless.

Bottom line
Almost all the people we know who have retired to 2 or more places are very happy about that lifestyle. They relish the variety and stimulation it adds to their life from new friends and experiences. The cost can be a significant, but not insurmountable hurdle. And, particularly for snowbirds, there is no greater joy than reading about a whopping snowstorm instead of being there shoveling out the driveway.

For further reference:
Snowbird’s Leaving for the Winter Checklist
Our Ideal Snowbird Pairings
How to Find an Affordable Retirement
Budget Strapped Parks Trade Retirees Work for Rent
How to Retire in Style and on a Budget

What do you think? Please share your perspective and experiences about this topic. Have you tried it and loved it – or not so much? What makes a good pair of places to retire? Let us know!

Posted by John Brady on April 18th, 2011


  1. […] by on April 20, 2011 Amplify’d from […]

    by Why Your Best Place to Retire Might be… 2 Places — April 20, 2011

  2. 1. “Almost all the people we know who have retired to 2 or more places are very happy about that lifestyle.” Well, yes, they would be. If they weren’t happy with choosing two(+) places, they would have only one.
    2. I live in West Palm Beach, Florida and Burlington, Vermont. I miss neither Florida in the summer (hurricanes, tornadoes, heart and humidity) nor Vermont in the winter (snow, freezing, ice). The weather in winter Florida is warm and dry – much like Vermont in the summer.
    3. To offset expenses, establish Florida residency (driver’s license, voter registration card, passport, IRS tax filing address). Spending six months + a day helps. Florida is a low-expense state: no income tax, farmer’s markets with dirt-cheap, fresh produce (tomatoes, grapes, pears, apples @ .99/lb), no heating and very little A/C required, extensive senior services and discounts.

    by oldnassau — April 20, 2011

  3. you should talk about the park models in AZ(and other places) 29-50k plus 5k a year give u a large RV sized place to live and that is cheap…new or used all in big community with lots of activities. they are all over phoenix AZ i wish their were more in LV area and every where else

    by greg rudowsky — April 20, 2011

  4. For anyone with health related issues, don’t underestimate the potential problems with coordinating medical care between locations. You’re going to need to have doctors in both locations in case of need. You’ll also have to be sure your doctors are willing and able to facilitate the transfer of information between locations. Not impossible, but a primary consideration when looking into multiple retirement locations.

    by mickey — April 20, 2011

  5. Even though my forum post has turned up some intriguing “middle of the road” climates, I am also still considering this approach, so thanks for the good info, both pros and cons (certainly “con” things that never would have occurred to me). One suggestion has me puzzled though:

    “You could reverse the seasons and rent for a fraction of in-season rates (while renting your opposite home out at high-season rates)”

    Wouldn’t that completely defeat the purpose of the 2 place retirement?

    Greg’s comment about the Park Models sounds like it needs some research too ! As does the turtle life !

    by scottp — April 20, 2011

  6. People who live in location for only several months out of a year might find it harder to cultivate as much social support as those who are full-timers in a location. It can take a little more time to get back into the social swing of things when you’ve been gone for six months.

    Jan Cullinane, The New Retirement: The Ultimate Guide to the Rest of Your Life (Rodale)

    by Jan Cullinane — April 20, 2011

  7. Forbes and Pew rate Wisconsin as one of the 9 states in fiscal peril. We are planning on moving to Texas for 6 months and 1 day because they have no state income tax. Texas is also fiscally sound. Forbes says that Florida, California, Ill. Arizona, etc. are in fiscal peril. So, I am worried that taxes in those states will go up. I think for sure they will go up in Wisc. so we are ready to get out of dodge. We are just entering retirement so busy researching all this.

    by Susan Foster — April 20, 2011

  8. Is there a website or blog where people discuss avoiding taxes?

    by Susan — April 21, 2011

  9. We became full-time RVers with our address of record in we go with the wind and can enjoy all 49 states for as little or as lengthy a time as we choose….when they build a bridge to Hawaii, we’ll travel there as well.

    by Beverly — April 21, 2011

  10. States with low or now income tax sound wonderful but, rest assured, they make it up with other taxes and fees. There are no income taxes in Tennessee but the city of Chattnooga is busily “incorporating” surrounding towns so it can enlarge its property tax base. We will soon have to pay both county and city. Sales tax is high – 9-1/2% and they tax groceries too. There is a website that compares state taxes. Try this:
    It takes a lot of homework but the perfect place is where you are happy!!

    by Holly — April 21, 2011

  11. […] A limitation of this survey is that articles published earlier in the year had a head start on ones that came later.   When we looked at the top 50 stories of the year we were pleased to see many articles get high readership – so please don’t take the Top 10 list as the definitive one. You can use the News Categories on the side of this page to scan for articles that might make your retirement quest easier. That way you won’t miss practical features like “Our Best and Worst Tips for the Newly Retired“, “Why Moving to Florida Might be a Good Move – And How to Do It“, or “Why Your Best Place to Retire Might Be 2 Places“. […]

    by » Top 10 Retirement Articles for 2011 Topretirements — December 26, 2011

  12. Comment from Dave:
    Your article sums up the complexity of this option quite nicely. My wife and I are currently approaching this question. The summers in VA are dreadful – hot, humid – and winters are fraught with more ice than snow. Having moved back to the east coast after 8 years in SoCal (Ventura)…well…we often wonder if I should have not taken the career change. In any event – both of us will be retired by July 2017 – maybe sooner for me. We’re both NJ natives, but we’ll never go back – not matter what Bonjovi says.

    by Admin — December 20, 2016

  13. This is the direction my wife and I are looking at when we retire in ~3 years. We’re starting to look at “primary” places now, with a Hawaii condo coming a bit later. We’ve narrowed our anchor location to Oregon/Washington/Arizona/Austin/Carolinas/Michigan…in other words, continental US 😉 Got a lot of work to do to choose the location, then find a place. This website has proven helpful!

    by GregW — December 21, 2016

  14. Great article! Presents great options for everyone regardless of what their situation may be. An especially great idea for me is to rent my warm-weather climate home for the next few years and move to a cold weather climate. For me this is a great tax option allowing me to fix up my rented home while deducting expenses off my taxes before I move back to it when I reach an older age when I plan to remain in the home year-round or at least during the warm season where I live. Also, it’s a great option for increasing my income and saving money for when I’ll need it most! Additionally, the decision will also save money in that rentals in the northern-tier part of the country are much more favorable during the winter than summer months! Finally, it’s an especially great option if you have family or friends living up-north colder climates. Furthermore, if able you can always take a week or two to travel to a warm-weather spot during the winter months when you’re up north and need a break from the cold. Granted, there are some disadvantages…one I can think of is preparing your home to rent and possibly moving some of your things to storage and back during the duration of time while you’re gone. There are pros and cons to most decisions, but this one is well worth considering. Hope this information was useful to some readers as much as this article was to me! Thanks again!

    by Thomas S. Hancock — December 21, 2016

  15. PS: Regarding my above article, this option allows having someone else pay your monthly payments for half a year while your primary owned residence is increasing in value! Plus, it’s a tax write-off!

    by Thomas S. Hancock — December 21, 2016

  16. Summer in Ohio and winter in Disneyland for adults at The Villages, Florida: Priceless!

    by William Stevens — December 21, 2016

  17. Nice idea, but noticed from some of my neighbors that as they reach their 80’s they don’t want to do the traveling back and forth every 6 months.

    by Mary11 — December 21, 2016

  18. Is it true that in some states you have to pay state income tax even if you reside there for less than half of a year?

    by Florence — December 22, 2016

  19. I tried the two homes scenario. That got old really fast. Closing/opening up the houses got to be a pain. Something I wanted would always be 1700 miles away. I had a dependable person to supervise my Florida home when I wasn’t there, but not so the Minnesota home. The drive back and forth was not fun. Neither was paying two sets of property taxes and association dues. So this year I said–enough! Sold my Minnesota home and am now full time in Florida. Still in the process of weeding out all the duplicate possessions. If I miss people in Minnesota, I can always fly there and back. Did that for Thanksgiving. More likely, they come to Florida for the winter, so I can see them here.

    This is just my experience. Your experience may be different. I do have friends in Florida who happily commute to their northern homes every year.

    by Linda — December 22, 2016

  20. Generally, if income is determined by state law to be earned in a state with income tax, it is taxable in the state from where it came, regardless of where the taxpayer officially lives. This is most common when a person lives near the border of a state and works in the other state. But it could have some application to retirees as well. Check with your professional tax advisor.

    by Clyde — December 22, 2016

  21. My question is, what would be the best website to visit to find a reasonably priced home, condo, or apt. to rent in the winter months. Preferring the Ft. Meyers or Venice areas of Florida. It would need to be furnished.

    by Dennis Fields — December 25, 2016

  22. I did a net search for “FRBO” or For Rent By Owner, and came up with several sites that list properties in Florida. Don’t know if these are the “best” but it could be a start. They are generally more reasonable since they don’t have to pay management fees.

    Several of them say “short term rentals” and list a price per night. If you see a place you think would work – I would suggest you contact the owner and ask for a weekly or montly rate. I would suspect they would be more than happy to rent like that and not have to worry about weekly housekeeping. (might also ask if that is available anyway) Good luck.

    by HEF — December 26, 2016

  23. People who rent their properties by the night or by the week are not necessarily going to want to rent them for longer. They make WAY more money renting them out for the short term. The housekeeping costs are included in the fee they charge.

    Good luck with finding a rental for this season! You’re late to the game.

    by Linda — December 27, 2016

  24. I was wondering if anyone has decided to live in one area and has a 2nd home not to far away they use for vacations and extended visits. We are considering this as an option for our difficulty in deciding between two locations. Has anyone out there has experience with this? How is it working out?

    by Staci — December 29, 2016

  25. Staci
    Actually we know a couple of people that do this, although not necessarily for retirement. We live near the shore and these folks live in the town a few miles away. During the summer they come down and live at the beach and hardly ever go back to the other place during that time. But being close to the 2 houses makes things a little easier. They love the change. Now they are getting a little older so lets see what they do – the shore house is winterized so they could move there year round.

    by John — December 29, 2016

  26. Thanks John
    We’re considering it so we can remain in a “tax friendly” state. Hopefully, we can swing it financially. We’ve been 2nd home owners, but unfortunately it wasn’t somewhere we could see ourselves being as we got older. Having two homes in closer proximity would make it easier to decide that never ending question “Where should we live?”

    by Staci — December 30, 2016

  27. HEF
    One good thing in being late to the game is that prices may come down as owners become more anxious to rent. I would check with Real Estate/ Rental Agents as well. They often have a list of “Last minute deals”.

    by Staci — December 30, 2016

  28. Vacation Rentals by Owner (VRBO) has been helpful for us. They offer both short and long term rentals in Florida.

    by Lynn Imler — December 31, 2016

  29. I have a question for those who have two retirement homes where one is vacant for a good portion of the year. What do you do about homeowners insurance for the time when the houses/condos are unoccupied? We have a condo in Galveston that we used as a vacation rental for the times we were not using it. We had special vacation rental insurance for it until we quit renting it and decided to sell it. Because the unit was unoccupied, we could no longer obtain the vacation rental insurance and needed to purchase very expensive specialty insurance that just covered the contents of the unit. The condo association covered the insurance on the structure itself.

    If you are say spending 6 months in each house/condo, do you just not tell the insurance company that the unit is unoccupied and take your chances?

    by LS — August 30, 2017

  30. LS, all you need to do is have someone check the unit/house every 30 days. That satisfies the “occupancy” requirement of standard form homeowners policies.

    by Doug — August 31, 2017

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