When Is The Right Time To Travel Or Live Abroad With Kids

Despite all the hassle, you want to travel or live abroad with kids. Exciting! As the global economy reopens, more families are wanting to travel or live abroad. This post will give you some food for thought as I’ve been thinking about doing just that over the next 24 months. I loved growing up overseas and have always wanted to live abroad with kids once I became a dad.

Growing up abroad, it was always a treat to meet new people, eat new food, and learn about new cultures. My parents' careers enabled them to live abroad with kids. They worked for the US Foreign Service and lived all over.

During my childhood, they were stationed in Manila, Lusaka, Kobe, Taipei, and Kuala Lumpur. Our final stop was McLean, Virginia for my high school years. McLean is 20 minutes away from the US State Department in Washington D.C.

Because I attended international schools for 13 years, I felt like I had a much richer childhood compared to many of my high school peers. All they really knew was the Northern Virginia region.

Most of them spent their entire lives there for elementary school, middle school, and high school. On the other hand, every summer I'd go back to see my friends in Taipei and KL. It was an absolute blast.

Living abroad helped me understand and embrace different cultures. For example, roughly 61% of the Malaysian population is Muslim. Thus, I had several close Muslim friends who shared their traditions with me. I'm certain there would be much more love and harmony around the globe if more folks traveled.

Going On An Adventure

As a father now, I often think about ways in which I can provide the best childhood possible for my kids while also creating a life of adventure for all of us. Traveling or living abroad with my two young children could be a blast.

“Best childhood” is subjective. It can be described as one that is filled with happiness, friends, unforgettable memories, abundant life lessons, adventure, the learning of at least one other language, and continuity in the family. If you live abroad with kids, what an adventure it will be.

Because my wife and I run an internet-based business, we have the ability to provide for a unique childhood experience by living anywhere. If we don't travel or live abroad, it would feel like such a waste. This is especially true now that the San Francisco Bay Area is so crowded and economically homogenous.

Before our son was born, we always noticed a nice uptick in our happiness when we traveled abroad. We traveled aggressively for five years before our we had kids.

For example, spending three weeks on the Hapsburg Trail helped us love our online business even more. Prague, Vienna, and Budapest are truly wonderful places to visit. It was a dream to spend the final week in Paris to watch the French Open.

Financial Samurai In Budapest - When Is The Right Time To Travel Or Live Abroad With Kids
Overlooking the Danube River in Budapest.

The following year, we spent three weeks in Asia, finally visiting the great temples of Angor Wat. And we spent a week diving off the island of Pulau Redang, Malaysia. It is unbelievable to dive in 80+ degree crystal turquoise water.

Pulau Redang, Taaras Resort & Spa - When Is The Right Time To Travel Or Live Abroad With Kids
Taaras Resort at Pulau Redang, Malaysia was amazing

One Problem If You Live Abroad With Kids: Childhood Amnesia

Traveling is enriching. Unfortunately, few adults can remember life before age three. This is something to consider if you want to plan the best time to live abroad with kids.

Even though I had specific country anchors in place during my childhood, I only have two memories living abroad between the ages of one and two.

My first memory was sitting in an outdoor restaurant in Lusaka, Zambia while I tried Pepsi for the first time. It was delicious.

The second memory was when I had to go to the bathroom, but couldn't because it was occupied by my dad. I banged on the door hard, but he wouldn't open it. So my mom had to clean me up in the tub.

One other memory I have before three was in Arlington, Virginia. I remember playing with my sister and babysitter in a makeshift room made out of sheets.

They say that kids don't remember much of anything under three. Only at around age five do children form long-term memories. Therefore, the right time to travel or live abroad with kids is at age five or older.

Living Abroad With Kids Keeps Life Exciting

I can't remember much before three years old from several countries. Thus, I must imagine others who've lived their lives only in one place might have a difficult time recalling their past as well. Everything tends to blend together if you don't go anywhere.

Sigmund Freud coined the term “childhood amnesia” to describe the loss of memory from the infant years. According to a study done by Emory University, they found that a child's earliest memories begin to fade around the age of 7.

Therefore, a family traveling or going to live abroad with kids under the age of three is not doing so for the child, but for themselves. My wife and I purposefully traveled as much as possible before kids. We knew we likely weren't going anywhere for at least the first two years as parents.

If you want to pick the best time to live abroad with kids, definitely take their ages into consideration. To provide the richest cultural experience for a child, look to travel after their toddler and preschool years. I'd recommend waiting until your kids are at least three years old.

Three Childhood Experience Models To Live Abroad With Kids

Based on the logical conclusion to travel after the age of three, we've come up with three different childhood experience models to consider for our family. Two are a hybrid approach with international travel. And, the third is a committed plan to live abroad with kids.

1) Anchor in San Francisco, and travel all summer and winter.

The easiest solution is for us to live in a diverse city like San Francisco for the next 18 years until our kids go to college. Every summer break we'll spend three months living in one or two countries as a family.

Then, every winter, we'll spend the 2-4 week break in another country. By the time our oldest goes to college, he'll have lived abroad for a total of 52 months, or a little more than four years. Our kids will visit at least 20 countries, thereby expanding their cultural experience.

Related: A Digital Nomad Lifestyle Is Worth Living

2) Anchor in Honolulu, and travel all summer and winter.

San Francisco, unfortunately, has the lowest kid density for cities in America. As a result, SF is the least kid-friendly city. Instead of staying here, we would move to Honolulu, one of the highest kid density cities in America that is very focused on family (ohana) living.

The advantage of living in Honolulu is that we also get to be close to my parents (but not my wife’s parents), and we can send our son to a school that goes from K-12.

In San Francisco, you have to go to a different school for elementary school, middle school, and high school. Thus, it's inevitable your kid's friends will end up going to different schools. The disadvantage of living in Honolulu is losing our social and professional networks we've spent 17 years building in SF.

But actually, our kid just got into a Mandarin immersion private school that goes from Pre-K 4 through the 8th grade. Therefore, if he loves the school the he has a home for the next nine years. Here's how to get into preschool or a great private grade school.

3) Completely live abroad with kids and come back to America during summers and winters. 

I like the idea of living abroad in three international cities for four to six years each once our son is old enough to attend kindergarten (age 5). The idea is to be in one city for all of elementary school, another city for all of middle school, and a final city for all of high school.

We'll use the summers and winters to come back to America and visit other cities close by to where we are currently stationed. Some places we'd love to live in are Amsterdam, Barcelona, Shanghai, Rio de Janeiro, Kobe, Tokyo, and Rome.

Which Childhood Adventure Would You Choose?

Angkor Wat At Night
Angkor Wat At Night

A big part of me wants to go all out and live abroad with kids once our oldest turns five. I did it for 13 years of my life and traveled internationally for 25 years since. It would be a blast! We could rent a fully furnished house and rent out our home in SF.

My wife, however, isn't so keen on the idea because she has never lived abroad for an extended period of time. Only summers in Japan. She's more keen on option #1 or #2.

She reminded me about the pain of having to change our business address, file different types of taxes, and all that type of stuff she deals with as the CFO of our company. We'd also have to go through the arduous process of applying to expensive private schools with limited spots.

Life is so comfortable now, but I long for excitement. I'm the guy who has to get out of the house and do new things every day. Whereas my wife can comfortably stay home for weeks.

Best countries for expats - When Is The Right Time To Travel Or Live Abroad With Kids

Biggest Concern Of Living Abroad With Kids

My biggest fear about living abroad for our kids' entire grade school life is them not developing lifelong friends from childhood. I don't have any elementary school friends I keep in touch with because I don't know them well enough.

I do sort of keep in touch with my middle school friends from Malaysia. But, the relationships aren't tight since they are so far away. Because I started high school as a new kid, I wasn't able to develop deep relationships either. There are really only two people from HS I keep in touch with. But, they are both on the east coast, so I hardly ever see them.

That said, we now live in the time of the internet, social media, and video chat with our phones. It's much easier to keep in touch today than when I was growing up.

I'd love to get everybody's opinion on what you think we should do, and what you would do if you had these options. If there's a different childhood model to live abroad with kids that I'm missing that could also be amazing. I'd love to hear it.

Related: Traveling With Kids: A Guide For Parent's

The Benefits Of Traveling Abroad For You And Your Kids

  • Potentially easier to learn a new language
  • Forces your child to open up given he'll have to make new friends at a new school
  • Gives her firsthand experience of things other children might only see online or in textbooks
  • Might make him more unique when applying for colleges
  • Creates more empathy and understanding for other people and cultures
  • May let her appreciate living and working in America if that's where she ends up
  • Make international friends in addition to American friends

With the Omicron variant raging on, my family still won't be traveling abroad with our two kids under 5 any time soon. We will likely wait until our daughter turns 5 in 2024 before traveling abroad. This way, both kids can remember and better appreciate their travels.

Protect Your Kids With Life Insurance

If there's one thing the pandemic has taught us, it's that life is not guaranteed. We must do everything we can to protect our children while they are still dependents.

Whether you live at home, travel a lot, or plan to live abroad with kids, please get life insurance. Not only should you get enough life insurance to cover your liabilities, your life insurance term should last long enough to get them through college.

The best place to get life insurance is through PolicyGenius. PolicyGenius will help you find the best plan for the lowest price tailored to your needs. PolicyGenius provides free, no-obligation quotes from the nation's top insurance carriers so you can get the best rate. When they compete, you win.

Life insurance gets more expensive the older you get. If you get sick, depending on the severity of your sickness, you might not be able to qualify.

Even if you already have life insurance, I highly recommend checking PolicyGenius to try and get a better deal. Chances are high you're not getting the best terms. 

Utilize A Travel Rewards Credit Card

If you're going to travel a lot and/or live abroad with kids, take advantage of a travel rewards credit card. My personal favorite rewards credit card with no annual fee is the Chase Freedom Unlimited credit card. I've been a Chase cardholder for over 10 years and also do all my business banking with Chase.

Chase Freedom Unlimited

Here are the card's following features:

  • Earn unlimited 1.5% cash back on all purchases
  • No annual fee
  • 0% introductory APR on purchases for the first 15 months as well
  • Get a $200 bonus after you spend $500 in the first 3 months
  • Bonus cash back categories
    • 5% cash back on travel purchased in the Chase Ultimate Rewards® portal
    • 3% cash back dining at restaurants and eligible delivery/takeout 
    • 3% cash back on eligible drugstore purchases
  • Redeem cash back with no minimums
  • Rewards don’t expire as long as your account is open

When you can get 50% higher cash back on all purchase than the typical cash back card and not have to pay an annual fee, you are winning!

For further suggestions on saving money and growing wealth, check out my Top Financial Products page.

In addition, if you enjoyed this article and want to get more personal finance insights and tips, please sign up for the free Financial Samurai newsletter. You’ll get access to exclusive content only available to subscribers.

About The Author

118 thoughts on “When Is The Right Time To Travel Or Live Abroad With Kids”

  1. Extremely time reading for me. I must decide by tomorrow whether to accept a new position in Singapore. We are family of four, kids ages 14 and 10, currently living in Arlington, Virginia. I grew up in Arlington and my parents are nearby so it feels like a place to call home. We moved to Korea in 2011 as I was offered a work opportunity there and my wife hails from Korea. At that time, our daughter was 5 and our son 1. We stayed there 4 years and then relocated to Singapore for 2 years, also for an expanded work opportunity. Perhaps we are one of those rare families, but I can’t say we were as fond of Singapore life as many expats reportedly are given Singapore consistently ranks of one of the best destinations for expats.
    In 2017, we relocated back to Arlington as I wanted to start my own business and felt USA was best place for this. Fast forward: starting a business was best choice of my career–I have since been working in Taiwan and Eastern Europe, which was a blast, while my family stayed based in Arlington. We wanted to give the kids continuity of education and community during this period.

    Ok so there’s the background. Our daughter, 14, is in an excellent school in Arlington-HB Woodlawn if you recall it, and would be there through high school if we stayed here. She is a rising freshman and really doing well at school. Our son is a rising 5th grader and also doing well at school and broader community. We recently purchased a house in Arlington with the intention of staying here at least through daughter’s high school years. And then I get an out of the blue offer to come to Singapore and work. The offer is a 2 year contract with no guarantee it could turn into 4 years though quite possibly could. The money is good but not stellar–we would be able to save money and of course we would have to shell out for international schools in Singapore, of which the education I suspect would be equal or perhaps only marginally better than kids are getting currently. I love a good adventure and want to say yes. My wife also enjoys a good adventure; however, the thought of moving again and having to establish new network of friends, new social groups, new calendar of activities for kids is exhausting for her even to consider. We, therefore, are likely to stay put in Arlington for the time being.

    International living and travelling is wonderful and invigorating for all the reasons many of you have mentioned. Still, transitions on the scale of a major move, especially in the formative teen years, pose unique challenges for us as opposed to moving when the kids were say in elementary school.

    1. It’s hard. I would have loved to have stayed in Kuala Lumpur for all my high school years instead of move in 8th grade. I could have made so many closer friends and so much more fun. But maybe I would have gotten in too much trouble.

  2. Jeff - Project Manager

    Hi Sam.

    I apologize for being late to the game, having just come across your article. I agree with all of your points regarding the benefits of international travel for children. It sounds like you and your wife are supportive parents based on some of your list of considerations. Given that, my 2-cents is to go with option 3 and travel as much as possible. (At least, that would be my choice.)

    My wife and I are considering taking it a step further by relocating overseas–perhaps Scandinavia or Australia/New Zealand. I work in a field that appears to be in demand so it seems like a real possibility. That said, there is so much to consider. Both of our children are in high school, which might make the transition difficult but they are both genuinely excited at the thought of moving overseas. It does seem overwhelming. Some of the pressing questions include, what would our kids do for college (in the States or overseas?) What if the career overseas does not go as expected? What should we consider regarding citizenship? So many questions. I would appreciate your insights regarding what it takes to make such a move work.

    Thank you in advance and my very best wishes on whatever decision you make.

  3. Hi Sam, we struggled with the same question. I recall reading on another blog post of yours that the shift in the market and the rising cost of living in the Bay Area was giving you pause and maybe having you consider creative ways to stretch your savings.
    I grew up in the SF Bay Area, and then lived in SF proper for more than 20 years. When our kids got old enough to go to Elementary school we tried to make it work for a few years but (as I’m sure you know) the lottery system is brutal and the HCOL weeds out really good teachers who just can’t afford to live there.
    We could have afforded to stay in SF but we chose not to. The bottom line was, we paid a lot of $$ for a mediocre school with mediocre teachers and no green space to stay in SF. I feel like it is a rite of passage for all San Franciscan parents to spend evenings fantasizing about moving out of the City and scrolling through real estate listings. And we finally gave in to that urge and moved out of SF to Seattle.
    I would encourage you to consider moving out of your HCOL home and life into somewhere more child-friendly in the US, but renting your SF place out and not selling it, if you can. We make enough from rent to pay our mortgage on both our house and our apartment back in SF.
    Now that we don’t pay insane property taxes, no state taxes, and our overall cost of living is about 2/3 what is was, we get to spend 3 months out of the year traveling with the kids. And when we are back in Seattle, we found a school with gifted, motivated and inspiring teachers and a school with acreage where our kids can run and play! I think it’s really important for kids to root somewhere and create long term friendships.
    I feel like we won the lottery. I don’t think we knew how bad SF was for families until we lived in a city that has the perfect balance of urban and kid-friendliness. If we could leave SF after nearly 40 years and not look back, you can too. Life sure is a lot easier when everyone around you isn’t killing themselves just to survive in a HCOL area.
    Move to a lower cost of living area, pocket the difference, and travel travel travel.

    1. Elizabeth Bello

      Sftosea, I love your advice! I am getting my son(4) and I ready to move to Central or South America. Probably Belize. I want us to have roots but travel much of the time. Living there, we can afford to travel all over the world.

      1. Elizabeth, have you been to Belize? What part are you looking to move to? I am a single mother and also am hoping for the same thing! May you prosper, where ever you go!

  4. We were living in Asia for 20+ years. My kids went to International School in HK last 5-12 years. With longer winter and summer breaks and much less expensive flight tickets, we did travel with kids for Thailand, Korea, Taiwan, etc.
    Now we have just moved back to SFO for almost a year and we have planned winter break to travel out again. (Yay!!!) And the kids themselves have stayed in Asia for their first summer already :)))
    I can’t agree more that children and we as adults have better global view and openness to different cultures.
    I m still missing the rich and different language environments in Asia

  5. I would go with option 3 if u want to really do it the right way but I am wondering how you would handle visas because u r not going there for work?

  6. Great post, Sam. It’s the topic I feel the most connected with, probably as a result of the global travel/living experience I gained over the last decade. Now, the family has grown and I have some of the concerns and share the same views on the virtues and drawbacks of global mobility in the context of your family.
    My story is a little different from you because I haven’t moved much during my childhood/teen years…my international travels started only after graduating from college.
    My wife and I are a binational couple (French/Argentinean) living in SoCal. Moved to OC from Europe for work when we were newly married in 2011. Fast forward to 2018, we have four kids aged 4, 2 and newborn twins who are just 3 months old. They are all American but are raised to be fluent in Spanish, French, and English.
    I was surprised by the lack of popularity of the option #3 (completely moving abroad) which may be the only way to immerse with a new culture, although I understand how challenging that could be when your wife is not fully on board with you. I lived in the Middle East for two years and feel that experience would not have added as much to my cultural sensitivity if it would have been otherwise.
    Our children, being born in the US, are raised in a third culture which is foreign to my wife and I. It also adds up to the geographical complexity of the logistics of having grandparents in different continents. We are probably going to move overseas again (I think it’d be good for them to get out of the only way of life they know here in North America) as I also long for the excitement of you new things you referred to. Also, don’t know much about the struggles of elementary-middle-high school transitions in the American system, although I am suffering the absurd cost of childcare here these days. It seems to be a good idea to live in Europe during their college years too because it’d be unaffordable in the US.
    Everyone seems to adapt differently to moving during childhood though. It’s a lot to ponder sometimes…what is that gives the best experiences and the least suffering.
    Thank you for writing this. I haven’t given you an answer but your post and the comments gave me a lot of viewpoints from so many other people too. Best of luck with your decision. Look forward to reading more stories on international family living.

    1. Hi, from the research I’ve done, it seems it is less psychologically taxing for children to live in various countries BEFORE the age of 8-10, when they begin to rely more on their peer group to handle the struggles of emerging adolescence. From what I understand, middle school-aged children fare the WORST with a major life change like moving abroad.

  7. Sam, I must admit that I’m anxious for you to move to Hawaii! I’d very much look forward to reading about the move, seeing pictures, reading about the process of buying a home there, learning more about Hawaii life – but I doubt you should uproot your family solely for the sake of producing satisfying Internet content for anonymous readers ;-) (Though maybe you could write it off on your taxes if you did!)

    It’s very interesting to read about this. For myself, I would like to spend a month to six weeks abroad in the summer, choosing different countries each time. This timeframe would give the kids some time back with their friends, while still giving them the benefit of exposure to cultural differences in a “slower” pace that more mimics the day-to-day lives of the residents there, not a “If It’s Friday It Must be France” pace: an opportunity to stay at an apartment, rather than a hotel, go grocery shopping alongside the native residents, build a little rapport, sink one’s teeth into the culture a little more than the tourist approach.

    I’ve been thinking much about developing friendships as I enter my 30s. I didn’t live abroad as a child (I did as a 20 something), but I moved around enough that I didn’t develop as many of the stable friendships that some have. I think it becomes more difficult to make friends as you get older, in some sense: everyone’s so busy, by and large, and also because your life is so specific to you that it can become tricky for anyone else outside your family, or maybe your coworkers, to fully understand your day-to-day. I do think it’s important to allow children some time in the same place to develop friendships. Friendships, when you’re young, are all about shared context, being at the same school, in the same class, on the same sports team. Proximity helps a great deal. After all, when you’re very young, you have very little shared life experience to draw on to develop a friendship, and you’re a long way from developing a values system that can also form a bedrock.

    Is the potential move to Hawaii a “we must decide by X date” (I would assume by the time your son starts kinder, if you have an ‘X date’) or is it more “if and when we feel comfortable, we’ll do it”?

    It also interests me that you have such a sharp memory of trying Pepsi for the first time. I have a very similar memory of my first time of trying Gatorade (lemon-lime, of course) when I was about four. Something about that sugar really sticks in the brain!

    As always, great blog.

    1. Great idea of writing off the entire move and living expense in Hawaii on the business! After all, how can I write about Hawaii living if I don’t make the move?

      The determination date will be either pre-school or kidnergarten. We’ve applied to all the pre-schools, and will see where he gets in. Then we’ll make a determination, and make another determination at kindergarten if we don’t move during pre-school.

      Good luck w/ your adventure!

      1. Remember the magic words “government per diem” for expensing business travel, especially to foreign countries or expensive areas. You can take a flat rate deduction based on total days without providing any receipts or other documentation.

        The GSA rate for New Zealand (lodging & meals) ranges from $214 – $431 per day depending on the specific area. That’s about $6,500 – $13,000 monthly which is *far* more than we’ll be spending during our three months. Translation: tax-free reimbursements from my business for anything beyond our actual expenses.

        It does help to have a business and actually *do* some real business during the trip. ;-)

        p.s. Hawaii per diem is in the same ballpark as New Zealand.

  8. We homeschooled our kids all the way k-12. We traveled quite a bit through the states and we went to Central America a couple of times and went to Europe for 6 weeks. I found traveling with small children 3-7 difficult. I felt traveling with middle school to be the easiest. High school was challenging as it became more expensive to accommodate “space and energy” needs. We tried three times to live for an extended period of time in a foreign country so that our children could learn another language, but it never worked out! One time Ebola scared us back to the states. So even though we didn’t accomplish that goal, we have a lot of great memories; the kids are now in college and are finding it easier to focus on college; the wanderlust feeling was satiated (they have “been there and done that.”) A VERY important word of advise: know your child(ren). Some kids find it very disorienting to move around quite a bit — and others thrive on it. Also be prepared for the unexpected! Good luck

    1. Thanks for the feedback. Do you feel homeschooling was the right choice? If so, why or why not?

      Which countries did you choose? Perhaps the choice of country has a lot to do with how much a family enjoys there? And the accommodations and school etc.

    2. Anthony Hermans

      Hi Geni,

      Your advice there are children thriving on moving around and other struggling caught my attention.

      We are a family with a 9 month daughter and 2 year son. My wife is from Nicaragua and I’m from Belgium.

      Knowing all the benefits for us and the children of living part-time in Belgium and part time in Nicaragua we’re concerned of the negative effects on our children’s development.

      We have two choices giving them full time schooling in one of the countries or move them around every 6 months.

      What would your experience and other’s recommend us?

      Warm regards,
      Anthony, Ivania, Marcel & Mia

  9. I had all the same questions you do before my kids were born. The reality is that what is important to you because you did or did not have something will mean nothing to your kids. If you give them a lifelong anchor, they will will thirst for travel and vice versa. We’ve travelled extensively with our kids, lived in three countries for long periods of time. My eldest (12) is already talking about wanting a large family with a dog, cat, fish and a snake and never travelling. We just got back from two weeks in China and if you are looking for somewhere to decamp it’s worth a second look, no tax on overseas income…Guangzhou is particularly nice.

  10. My dream world was option 1, however we wont be retired early enough so we are going for option 4. Live in one city in America, travel 1-2 year internationally until college but in about 4 years (ages 11-13ish) take a year off and travel the world while world schooling, come back and reassess.

    This is our daily conversation and a main focus of our blog.

    I traveled all over as a young athlete and lived in a few countries; I most definitely want to give my kids that and prepare ourselves for more and constant travel when we fire as they enter college. In fact we already took 2 years off to ‘reverse retire’ when they were little, moved to a lower COLA country and were able to both stay at home with them when they were young. Best of both world.

  11. I am currently spending the summer abroad with my teenage son. Three months here then he enters college. We’re staying in an apartment in the heart of an old town where there’s plenty to do and see within walking distance and even more within train or bus.

    I am working most every day, including remote video meetings three or more times a week. During that time he does his own thing. But we can still have an hour or two even on work days and full days on weekends, which end up being akin to long weekends for us due to the time difference. Though, I am frequently working on weekends also due to the nature of my project. For example, today is Sunday, I have to put in an intensive day to prep for an important meeting, but am doing so while gazing out at a courtyard with birds and the sounds of the vendors setting up shop, feeling relaxed after having taken yesterday tour the coast by slow train, though I still got quite a lot of work done thanks to a text-to-speech app called Voicedream and airpods.

    The trip is mostly for language and cultural immersion as well as to pass on travel tips and related accumulated wisdom that is best meted out as the situation arises. These lessons will be beneficial to him as he travels on his own later for work or personal enrichment and I’ll feel better about him not having to learn these things on his own as I had to for myself.

    The tween years can be a very good time to travel if you have participation to help out with household chores. If anyone is on a different sleep-wake schedule or is spending lengthy periods chatting with friends online best if each can have a separate space of their own. Teens are even more enjoyable travel partners, at least once you’ve navigated the attitude adjustments that come with that stage of maturity. I much prefer traveling with my sons than traveling with most adults.

    I’ve traveled with my sons all along the way. They’ve been to numerous national parks & domestic cities, several road trips, seven countries on three continents. But this trip is perhaps the best one yet. I’m passing along my travel wisdom to a (mostly) adult mind ready willing and able to receive it, while still having a (mostly) enjoyable travel partner. You can start to share observations about nuances, and they can also start to share their knowledge about history and culture they’ve learned in school or from video games. Don’t laugh — my son aced the AP history exam based purely on what he learned from historically accurate multiplayer video games.

    Each travel experience is unique and has its own value that is incomparable to any other, but this is probably the most satisfying one yet.

  12. I’ve never been to Hawaii, but I’ve been told by many people that the lifestyle there is very different – more laid back. The people in general are nicer and not always on the run – I don’t have any first hand experience with this.

    I’ve been to SF and while I enjoyed my visit, I just cannot imagine living there. I am not a big fan of the cold weather and I thought November was too cold for me :)

    Option 3 would be the most difficult. Having to deal with VISAs, language barrier, transportation. I thought it was a pain when I was just visiting. But I think out of all 3 options, I would pick to do option 3 first. I would do it for a few years and if it doesn’t work out, I would still have 1 and 2.

  13. Things have changed a lot since you and I were in school as kids. With Facebook and the internet, people can maintain connections and even strengthen them from thousands of miles away. I live in Europe but still keep in contact with several friends from middle school and beyond. Given the same technology, I’m sure today’s children will be able to keep in touch with elementary school friends indefinitely, if they want.

  14. Sam – you have many and great options, and funny thing is, probably your boy will turn out great irrespective of which option you choose.

    Writing to you as a South African who has been an expat for 8 years, living in Miami Florida, Sao Paulo Brazil, Mexico City Mexico and now Windsor United Kingdom. Moving for my work to these 4 interesting countries and 4 interesting cities. Our two children, 7 and 3 respectively were born during our expat lives and therefore been traveling since birth.

    You are right, probably they wont remember the early travel, but I do believe they get the language development benefits from being exposed to 3-4 languages from birth on. Grandparent relationships are maintained through Skype, daily WhatsApp and various social media’s forums, while complimented by various “local” grandparents we develop relationships with.

    Kids are still young so difficult to say whether relationships will last, but I am convinced the skills of being adaptable, culturally agile and socially outgoing will last.

    The important thing is to provide them with love, love and more love. We also try to break the bubbles – it is easier than you think to move around the world but never connect with whats real locally. The richness of it all lies in connection- and therefore I think the three month drop ins over summers might not be the same as living in various countries for 3-4 year stints.

    Besides whats best for your child, you might also consider what is best for your location independent business – different tax structures can save you substantial sums.

    Enjoy deciding! But whats more, enjoy living it!!

  15. Realistically, I think #1 or #2 is your best option. I can’t say it matters to everyone, but if you feel like it’s important to build roots then these would be your best choices. If you spend your childhood in one location, you do develop pride in that regardless of whether you still keep in touch with the people from the past. So on one hand you have HI, which is fantastic because of it’s Ohana vibe, or SF which is great for it’s diversity (even if it is gentrifying). Living aboard a few years here or there is more to satisfy the wanderlust of the parents, which I can relate to. But as your son would grow older, it would be difficult to say a place he spent 3-4 years in at a time feels like home, and especially if you don’t no longer own the same property you grew up in. But if you spend 10+ years in a city, that city becomes yours and the relationship with the city grows beyond the house you live in.

    1. The first two options are definitely easier for sure. But sometimes, staying in one city might become a disappointment because that city changes a lot over time.

      For example, I like San Francisco in 2002 better than I do today. It’s way too congested and pricey. A lot of long-term residents here no longer like it because our city lost a lot of its old world charm.

    2. I enjoyed reading your blog and learning that I’m not the only person who can’t keep still for a minute. My network don’t understand why I love to travel and move around so much especially after having a child.

      I would choose option 3 until the child turns 7 then opt for 1 or 2. They get the best of both worlds and have the opportunity to establish lifelong friends. I am doing that for my daughter. We lived in 2 international cities and traveled like crazy until she turned 6 then we moved back to New England and will stay put until she’s 18 but we continue to travel every summer.

      Bear in mind that once your child becomes a teenager they might want to land a summer job in their hometown which adds a little challenge to your plans. I get a strong feeling you will want to continue traveling after your kids graduate so it might be best to do option 2 so they have extended family members for emotional support while you are moving during their adult years.

  16. I voted for Other b/c all the variations are good depending on your values. There are so many variables including career aspirations (and how portable these are), extended family obligations, financial means, health issues, etc. In our case, my husband and I did some international vacations with our kids, and we encouraged them to do study abroad or other structured programs where they didn’t have to be with us. But we are reserving most of our travel for when we’re empty-nesters.

  17. Aaron Meredith

    My family of four (kids now 6 and 9) just repatriated back to the USA after 3 and a half years in Switzerland. Wonderful experience! We did, however, have my wife’s mother and brother next door in Germany, which was fantastic to connect closer to them while we were there.

    Couple of observations:

    Absolutely fantastic for the kids to experience a new culture. They also developed a strong sense of independence and confidence I don’t believe they would not have developed here. For example, my son’s daycare let kids cut wood with a saw at age 4 and walk home by themselves at age 5! My daughter was riding the bus by herself at age 6. Can’t get that here. It was awesome for the kids. Both are bilingual (tri-lingual if you count Swiss German). And, they pretty much rolled right into life here without much fuss.

    Having my wife’s family nearby made the experience that much better. Nothing like your mother in law looking after the kids for a few days while my wife and I got away for a long weekend in Barcelona! I think it would have been a bit tougher NOT having family nearby.

    One word of caution. Managing personal finances and investing while living overseas was hard when we got to Europe and got HARDER before we left. You must maintain a USA address to have a prayer of USA-based banks not freezing accounts, not allowing you to open accounts, etc. Several websites have completely shutdown access from outside the USA due to the new European privacy laws. I often felt like I had to be sneaky just to conduct business as usual and avoid problems although everything I was doing was on the up and up. Perfect example of managing to the lowest common denominator: Putting rules and regs in place to prevent the bad deeds of a few and everyone else pays for it. All of this is not a show stopper, but it was a significant impediment that needs to be thought through and managed carefully. I’ve enjoyed the past few weeks of unblocked websites … whahoo!!

    1. Interesting insight on managing personal finances! Hmmm. I know Personal Capital’s app, for one, doesn’t work outside the United States.

      One reason I bank w/ Citibank is because they were everywhere when I traveled abroad. I’m hopeful they will be in the countries where we will go.

      At what age do you think it’s best to introduce a second language to a child?

      1. Earlier the better regarding second language. Not possible to be too early. I’d even recommend hiring a bilingual babysitter from time to time to speak a different language to the little one. Amazing how fast they pick it up.

  18. I my earliest childhood memory was when I was 3 and have no recollection of any memories before that. Really nice that you had a couple childhood memories that young at age 1. We have a two year old son and taking him on his first trip soon. We know that he may not remember this trip but with easy accessibility to take many photos and videos, we can show him the places we went and how much fun he had. I think as he becomes older, he would be curious of how he was like when he was 1 or 2 and providing pictures and videos will really help.
    Option #1 or #2 would be best in my opinion. Although your son will have to go to different schools in SF at three times before college, their may be a chance that a few of his classmates will go to the same schools as him. Going through the school system here in SF, I had a couple of friends that went to the same elementary, middle and high school as me. The Honolulu option would be smoother for him in that regard where he goes to the same school throughout that whole time.
    And you have the summer to travel abroad and settle for a month or two so he can experience the culture of that country.

  19. “I’m certain there would be much more love and harmony around the globe if more folks traveled.”

    Reminds me of the following quote, which I have always found to be quite accurate:

    “Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one’s lifetime.”

    ― Mark Twain, The Innocents Abroad / Roughing It

  20. Excellent post. As a Brazilian living at Rio de Janeiro I’m very curious to understand why you consider Rio a good place to live.

  21. Once you kid reaches school do not move anywhere permanently that would affect their schooling. Plonk down and wait it out until after you finish school. You dont realise how socially destructive it is for a young person to be moved around alot and always be “the new kid in school”.

    I myself was moved around a lot and looking back can absolutely confirm it affected me in multiple ways, from keeping friendships, relationship bonding and more.

    Provide the most stable possible life you can for your children and hen do what you like once they are old enough to fend on their own.

    If you travel profusely with children and living all over the place they will never have a real home. I would almost go so far to say it is a selfish thing to do (and this is coming from a top 1% traveler!)

    1. May be traveling is a different experience for everyone? I’m not sure if I made it clear in my introduction that I traveled all around the first 13 years of my life and found it to be an incredible experience. But I do wish I stayed put for high school after middle school.

      It’s worth having an open dialogue and see how things play out.

      What are some specifics about traveling that messed you up?

      1. Haha I wouldnt go so far to say I am messed up!

        Growing up is hard enough without throwing in other variables. For me personally it was difficult to identify who i really was. You maybe right in terms of middle school, I went to 3 high schools and I think things become a lot more cut throat there.

        I had to start at the bottom of the social ladder every time and claw my way up, then move again and have to start over. It can be stressful.

        Nowadays I am quite nomadic but I dont really feel like I have a real home that I would have with a wider family and friends circle that would be there if we just stayed put in the country i was born in.

        When I have kids I am locking myself down and not moving once they start school.

        1. Yeah, I can imagine that three different high schools would be really, really tough. High school is already tough enough staying at one.

          We definitely do not have plans to move around during high school or middle school. The more I think about this, the more I like having him go to one school between kindergarten through 12th grade if he gets accepted in Honolulu.

          Why did your parents move around so much?

            1. I have lived abroad and would love to with my kids. However, every child is different and I think you need to look to your child’s developing personality to decide what is best. I have one child that would flourish and another that needs routine and community.

  22. German/Argentine couple here with two kids (7 and 9).

    As a megacorp expat family we spent the last 5 years in (your high school place) McLean (VA) before moving back to Germany a few months ago.

    For our kids this experience was and will be forever life enhancing. They went from speaking German and Spanish only with their parents to be also (like) native in American English.
    English ist their “kids language” now that they communicate with each other.
    Then they turn around and speak German with me and Spanisch with my wife.

    This is absolutely mind blowing for me as I was growing up in a rural German villeage without second language / much traveling before high school.

    Compared to other German kids in their age I observe that they have a much broadened view on life and they are in general more accepting and understanding towards other people.

    This alone was worth the hassle of making the move and relocate the family.

    +1 on loving your blog!
    Keep writing and Im eager to read about your next steps.

  23. Just because early memories fade away does not mean that the ephemeral experience does not affect these most formative of years.

  24. I thought about doing this about ten years ago. Unfortunately, my son’s health prevented us from doing so. Our biggest concern was insurance coverage. Will health insurance cover treatments outside of the US, particularly Asia?

    1. Probably not, but some single payer countries provide medical services for visitors and you can also purchase supplemental international health insurance.

  25. Ms. Conviviality

    My husband immigrated to the U.S. when he was 9 years old and never left the town he initially settled in. He even attended college in the same town. What I found attractive about my husband was that he is the kind of person that places importance on maintaining his friendships and it’s mutual for his friends too. He keeps in touch with 2 middle school friends and 5 college friends. We spend time regularly with these friends just hanging out, going on vacations, and doing business. These friends moved a few hours away but that hasn’t affected the friendships. A nice perk is I get to hear about all their past shenanigans and learn about a different part of my husband’s life and ultimately who he truly is as a person. My husband chose one of his college buddies as best man at our wedding and every year, on our anniversary, his friend would send a congratulatory message via text, phone call, or greeting card. During the most recent anniversary his friend sent us a gift card for a nice restaurant. I hear about couples that sometimes forget anniversaries but not our best man! Actually, now that I think about it, my maid of honor sends us nice wishes on our anniversaries as well. Although I didn’t have as long a history with my maid of honor since I met her as an adult through work we are like sisters after our 12 years of friendship. All of this is to say that our friendships provide so much joy in our lives and we never turn down an opportunity to spend time together if we can help it. It may be the case that it takes two to maintain friendships and lifelong friends aren’t a guarantee but I agree that providing for circumstances that would make it possible to have long-term friends is definitely worth it. I voted for option 1 because SF has so much to offer culturally, innovatively, and gastronomically but I could have easily voted for option 2 since growing up in paradise seems full of adventure and also provides quality time with the grandparents.

  26. Excellent post Sam. I feel like we have a lot in common. I am the same age as you, have a finance background, lived on 4 continents and travelled to many places during my childhood and college. As an adult, I have since travelled to many many more places with my wife and my 2 little kids. What we don’t have in common is that I haven’t quit my day job yet, as I enjoy what I do, it’s low stress, high pay, flexible hours, plenty of family time and vacation and I am not sure if my nest egg is big enough.

    I agree wholeheartedly that growing up around the world gives you a unique perspective on life, and I really wish I could give this gift to my children in some form. Seeing different places and how people live is the best way to learn about our planet and our species. Traveling somewhere out of your comfort zone for 2-3 weeks vacation is nice, but very different than longer slow travel or living in a place.

    I have been pondering very similar options to you, specially since my first child is about to start K and I live in NYC. To me the least attractive option is obviously to not travel at all and stay in the US. I would go mad. We thought we would slow down traveling once we had kids, but it never stopped! We take the kids wherever we go. The trips are now different, more painful, more tiring and intense as we don’t slow down, but also much more fun, specially seeing the world through our little kids eyes.

    We are entirely aware that any trip before 5 (maybe even 6 or 7) won’t form a concrete memory for our kids, but the travel is about us and we just bring them along for the ride. They might be more accustomed to travel going forward also. Kids love some structure and routine, so we do let them do their thing for several hours every day during trips. Like you, some of my most distinct memories before 5 were in strange places eating strange things or experiencing things unfathomable to most Americans.

    It is also true that kids below 5 don’t need anything too fancy beyond a playground, some sand, water, crayons, toys, etc. But that doesn’t mean they can’t or shouldn’t travel with you. They are highly adaptable and their brains are like sponges.

    Enough rambling, my thoughts for my family are that we will setup a home base in a few years in CA (not the Bay Area aka mega rat race like NYC) or maybe even HI, I would ‘retire’, we travel parts of the world during the summers for 2-3 months. We would perhaps live in another country for 2-3 years as well. This would be plan A. This way we can have some stability, and we can also see a lot of the world together traveling slowly instead of a 2 week vacation. The most ideal scenario (plan X) would be to live in 3 different parts of the world (for example one in Asia, another in Africa or South America, and third in Europe) for elementary/middle/high allowing lots of local and nearby travel. If that plan never works out, I will keep working, but at the very least travel for 1-2 months per year with the kids (plan B). Anything less is not an option for me, as I owe my kids the world education I cherish.

    I wish you luck with your decision and will be following closely. It’s great that your wife is on board, and your son is too little to have any say!

  27. We’ve shuffled all over the world but we have, I think, stopped now that our oldest is in kindergarten. I think he has a right to stay fairly still in a stable environment through his school years and adolescence so he can figure out the world with a sort of coherent frame of reference.

    It’s not just a friendship thing, or just a roots thing – I think being based in one place through those formative school years will help our kids know who they are, by knowing where they came from.

    That having been said a) we chose a place to settle based on the great facilties for kids a la Honolulu and b) we travel a LOT during the holidays.

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