Thinking Ahead

As mentioned a short while ago, Brett and I have started discussing where (and even if) we want to settle when the Big Adventure ends in May 2019. There’s much to consider, and still lots of unknowns right now, the biggest being where YaYu will attend college. That information alone, once we have it, will have a profound affect on our decision, but in the meantime there are things we can begin to talk about. Brett and I have gone back to our tried and true method of developing lists and spreadsheets, and looking at the pros and cons of different options. Once again, we’re taking our time to come to the best decision for the direction we’ll take once the Big Adventure is over in May 2019.

For the time being we’ve been putting together a list of the things that are important to us, or that we believe will be in the future. We haven’t particularly ranked anything yet, and none of the points listed below is yet a deal-killer. Some of the things we are considering so far are:

  • Do we want to settle somewhere or keep traveling? Everything will revolve around our answer to this question.
  • Cost of living: We’re pretty sure we’re going to want to continue traveling in some form, and the lower the cost of living if we decide to settle somewhere, the more we will have for travel.
  • Taxes: We will want a location with a good tax environment for retirees that doesn’t tax Social Security, has a lower or no tax on military retirement, low sales tax, etc. (We’re allowed to dream, aren’t we?).
  • Walkability: We do not want to own a car again, if possible. We would prefer to live somewhere where we can walk or use public transportation for the majority of tasks, and use ride or car share for those times when we absolutely have to have a car.
  • Culture: We’re mainly thinking about having access to classes for enrichment, but would also like a variety of other other cultural offerings nearby if possible, like art museums, theaters, etc.
  • Health care: The availability of good medical care, specialists, etc. will become even more important as we age.
  • Travel & transportation: If we settle, the ease of our getting to other places and for our children to come see us will be important.
  • Weather: While we would prefer sunny, warm weather, we (me especially) also would prefer someplace with less humidity if possible. We’re also not crazy about living somewhere that gets a lot of snow, especially since we’d like to walk a lot for as much of the year as possible.

So far, we have come up with four general location options with pros and cons to each one:

  • Return to Kaua’i: The thought of leaving here permanently is difficult to think about, but we’re not sure it will make sense to return if all of the girls are attending college, or living, on the mainland. Especially since neither we nor they can afford the cost of them (and eventually their families) traveling here every year, or us to the mainland to see them in all in the various places they live or will live. However, if YaYu ends up attending the University of Hawai’i, it will make sense for us to continue to live here, for a few more years at least. We would move to a smaller, more affordable space on the island, and perhaps even buy a condo here (although local HOA fees have pretty much priced us out of the market).
  • Settle somewhere on the mainland: If YaYu ends up attending college on the mainland, it will make much more sense for us to resettle back there somewhere, as it will be easier to see the girls and for the girls to come and see us. It’s also easier, believe it or not, for our son and family to travel to the mainland than to come to Kaua’i from Japan. Where that somewhere might be though is the big unknown. Living on the mainland would be more affordable overall, and we would probably buy something small, a true pied à terre so to speak. Brett and I dream of being car free and able to get to places by walking, using public transportation or using a ride-share or car-share service when necessary, and there are locations on the mainland where we could make that dream a reality.
  • Relocate overseas: The opportunity to live in a different country and experience a different culture still greatly appeals to us. Having lived overseas twice (in Japan) we know many of the ins and outs, pros and cons, and pitfalls of overseas living. It would mean a major, major lifestyle change and affect the whole family so it’s currently not as viable as the two options above. Still, it’s not out of the running. We both agree that if Japan ever offers a visa for retirees (highly unlikely) we would move there in a heartbeat.
  • Continue traveling: The Senior Nomads, who have been traveling non-stop for the past four years, were the inspiration for our own upcoming Big Adventure, and we are not ready yet to write off the possibility that we will enjoy our experience enough to want to keep going for another year or longer. There are so many places we want to see and that we won’t be visiting on our upcoming Adventure, and we may decide we just want to keep traveling for a while longer.

I am grateful we have so many choices, but there is a great deal to consider before making a decision. Thankfully nothing has to be decided in a hurry. Both Brett and I are physically, mentally and in good (enough) shape financially to take on any of these options, and all of them appeal to us in one way or another. We’re currently leaning toward one of the first two options, but will reevaluate our position as the year progresses and eventually come up with a firm decision about our future direction.


17 thoughts on “Thinking Ahead

    1. We haven’t a clue right now – haven’t even started a list. Portland spoiled us when it comes to walkability and public transportation options, but there are lots of options out there. We just need to do our homework.


    1. It’s been discussed, but not sure we could handle it financially. The option of spending part of the year in one place, and the other half in another makes a lot of sense though.


      1. I like the snowbird idea. Since you and Brett seem to prefer a nomadic lifestyle, maybe you could spend the winters in a different warm weather location each year and then either return to a permanent ‘home base’ for the summer or also stay in different places for the summer so you’re not dealing with home ownership (if that’s not something you want to do). That way, you’re not tied to living in the same place for years and are free to move around and be closer to your kids, wherever they are (if they aren’t living near each other).

        However, it’s just my opinion, but I feel you shouldn’t even think about any of this until you know where YaYu is going to college. Even then, kids can change their minds and not stay at the same college for the whole four years, so who knows, 😉

        After just living through another apocalyptic nor’easter, I’m ready to get out of here! A nomadic lifestyle is appealing.


      2. We like the snowbird idea, but not the thought of maintaining a couple of residences, or having to look for a rental twice a year. We’ll probably settle on one location for a home base and then work our travel schedule around the seasons/weather there – we still intend to travel to Japan for three months every year, for example – and want to do other traveling as well. As long as we’re able we want to keep moving.

        Right now all we’re doing is setting down some not-very-firm perimeters for what we might look for in a place to land when the Big Adventure is over. Where YaYu goes to school is the big event driving everything now but thankfully we should know more in about three weeks! Decisions start rolling in next week.


  1. Wow! I had no idea how tight Japan was about their immigration. Can you live there for 90 days, leave for a few weeks and then do another 90 days? Is there no provision for family members?

    We are enjoying Delaware. No sales tax. Small houses at a reasonable price. John Hopkins health for retirees. I think we paid $50 in personal taxes this year. Dover provides lots of hops. Amazing produce from local farms. Walkable downtowns. The down side is that it is not the West—which we love and miss. We will be here another ten or so years, then we will, probably, land in ??? we have no idea.

    Will look forward to your choices and decisions.


    1. Immigrating to Japan is tough. It took our son nearly 20 years to get his permanent residency there even though his wife is Japanese, he has children, owns property, speaks Japanese at a superior level, has a permanent job, etc. He could sponsor us, but only if we were destitute, which we’re not (and never want to be!). The 90 days in-country, leaving for a while and then coming back used to be doable, but they strengthened the law and now you can only spend 90 days in country within a 365-day period. My son has advised us against staying for 90 days only because we couldn’t come back in if there was an emergency.

      Brett is from Maryland, and we did two tours there so are familiar with Delaware and liked it. But we are west coast people at heart, so I sort of feel safe in saying we’ll most likely stay in the west if we do settle somewhere. But who knows right now? There are so many things to consider, including where the girls end up.


  2. Consider Tucson! As I look at possibilities for my own retirement a few years out, buying a small pace in Tucson to winter in (and still spend late Spring, Summer and early Fall in Portland, where I live) appeals greatly. No sure you could go car-free, but Tucson does have a great central area, is diverse, has a university so supports your life-long-learning goals, has a military presence so may support your health care etc. and is politically more liberal than the rest of Arizona. Also real estate prices are quite low and there is beautiful scenery and hiking opportunities, and it is close to Mexico and NO HUMIDITY.


    1. I love Tucson! I attended UA for a while and while I ended up leaving I enjoyed my time there – I lived in an apartment somewhere around Campbell Avenue and 6th (the apartments have been torn down, I think). I wonder though if there are still areas where you could go car free?

      My parents both graduated from UA – they met at a sorority-fraternity Valentine’s Day dance. They lived in Tucson for a while, and I’m named for their landlord (a wonderful person 😅). We visited Tucson often when I was young, and often went down to Nogales. I still have a real fondness for the area – it will be considered!


  3. It’s great that you can start fresh after your travel adventure. I look forward to reading more about your future direction.


    1. I’m grateful we will have the time to really think and talk about what we want to do next. There are so many variables, but it will come together. We’ll keep everyone posted!


  4. Given your history and ingenuity, I’m sure you’ll do your research and make a good decision. I look forward to your ongoing posts. You are a bright spot in my inbox. 🙂


    1. Thanks so much Laurel! I always enjoy hearing from you too!

      All we’re doing now is setting down some perimeters, but they’re still very, very fluid. Things have been quiet around here (and that’s about to change) so we’ve had some time to think a little bit about the future.


  5. We face the same dilemma as yourself. Not tied to any one place and we do have similar requirements. We took Hawaii off the table because as you say HOA are so expensive. We are current California residents but decided we do not want to pay such high state taxes or property taxes. I think people give too much weight to sales taxes because truthfully unless you are a big shopper what impact does it have.
    We have decided that our likely destination is Munich, Germany. One thing that has become obvious over the past few years is we want to live in a more tolerant society that is inclusive of immigrants, which we are, and the US is no longer that place. Germany would give us a central location to explore Europe, groceries are cheaper and better quality and don’t even get me started on the difference in health care costs.
    If you are seriously thinking about the overseas option, remember the tax implications. I believe UK and Germany are two of the few countries that will mean the US does not withhold taxes on your SS.


    1. Wow! I’d love to hear more about Germany, and relocating there. We’ve looked into both France and Portugal for immigration as they’re are retiree-friendly, more tolerant, and housing is affordable and healthcare there is excellent (and much cheaper). It would be a MAJOR lifestyle change for us though, putting us further away from the girls and our son. Our kids all say “go for it” though if it’s what we want to do, so who knows?

      I’m from Southern California, and there are a couple of places I could easily go back to except California is now way too expensive as are the taxes, although those aren’t as bad as they were now that we’re both over 65. The areas I like are also busy and crowded.

      The HOAs here are crazy. They start at $800/month and go up from there.


      1. I would caution against France. It was originally on our list, however if you fall into the category of being classified as a full time resident for tax purposes watch out. They have strict laws on inheritance for example.

        Like you want to be in a location where we are not required to have a car. We want to be able to walk out our front door and be able to access supermarkets and groceries and have things to do. Berlin is another interesting place that we considered but for me it is a bit like San Francisco, youth oriented. Nurenberg is probably my favourite city. Munich has an excellent public transport system and is very walkable. It also has many major train links ie. sitting around thinking about what to do why not take a train and be in Salzburg for lunch a few hours later. The other thing we like about Europe is prices are expensive to buy, but landlords are more likely to be professional in the sense that they are buy and hold for many years, not looking for a quick flip which has burnt us here having to move. Take a look at Mr Lodge for short term rentals in Munich. These are high end rentals, so imagine what prices are available for ordinary rentals.

        Lisbon is a beautiful city and we enjoyed it so much. The people are fabulous. However, not sure how the cobblestones and hills will be on an aging body and I did not find the public transport so easy to access.


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