In 2017 we did it. Our family of four spent four months travelling around Southeast Asia, we called it “Four for Four – Cheeseburgers in Asia.” We communed with elephants, we soared across the Laotian jungle, we licked the most delicious peanut sauce from our fingers, we laughed with faces that spoke no common tongue to ours. Four months away from work and regular life. Four months exploring different landscapes and cultures. Four months of intense togetherness.
Many people have asked us how we did it.
This post is such a description – how we managed our jobs, our money, the kids’ school, and our attachments back home. If you want to read more about what we did, I included some links to adventure blogposts at the bottom of this post.
Also, this blogpost is an invitation to my new blog project. I am back in Bellingham, Washington, and I have been building a new business called Trail Financial Planning.
We do financial planning and investment management for regular people. Primarily, we work with families like us. People with kids, with businesses, with values; people who care about life, and they way they live it. As part of that endeavor, I blog about financially related matters that matter to me and my family – paying for college, retirement, taxes, our investments, etc. My blog posts include:
If you are interested in following that blog, you can either:
- send me your email directly (send email to firstname.lastname@example.org), or
- go to Trail Financial Planning “contact us” page, and enter your email there.
This blogpost is also a taste of financial planning. It describes how we set a goal, and set about carrying it out. We needed intention, money, time, and a bunch of logistics planning. I’d be lying if I said it was easy. But, I’d also be lying if I said I wasn’t proud of us. I usually don’t like to make “brag-media” posts, but I know a lot of people are interested in doing something like this with their own families. So, this post may get a little braggy. Hopefully, this post will inspire others to reach for their big goals in life.
Here is a description of how we pulled off “Four for four.”
Step 1 – We built intention.
In 2013, Amy and I went out on a dinner date. Our dinner dates are infrequent, and often careen into existential conversations like, “What the hell are we doing with our lives?” While I was looking at the bill, sipping the last of my wine, we started talking about travel and trips with our kids. At that time, Mia was in 5th grade, and Porter was in 2nd. We had several trips we wanted to do, including a longer overseas travel experience. On the back of the restaurant receipt, we listed the places we wanted to go, and the time available. We figured we could pull off a semi-big trip every other year.
Travel goals – Southeast Asia, Africa, Europe, Mexico, Central America, and a longer travel experience.
Time resources – Seven summers before Mia would finish high school.
Step 2 – We planned the time.
We decided a four month trip made good sense for our family, and for Amy’s business. We identified Mia’s 7th grade year as the right time – after she had a full year start to middle school, but before 8th grade and high school when school might feel more academic.
We circled the year on the receipt, and told the kids about our plans. They took the news as kids often do about something totally incomprehensible:
Mia, our 11 year old, looked at us thoughtfully, “Uh, ok.” Then her brow furrowed, “I guess so, but like when? Which grade will I be in? Where will we go? How will we get there? What would I do for school? What would I eat? What about Josie (our dog)?” She is her mother’s daughter.
Our 9 year old boy, Porter, responded with “Uh, sure.” He is his father’s son.
We started telling others of our plans. By writing down our goal and saying it out loud, we gave the trip a certain destiny.
We went back-and-forth about what time of year to travel. Amy and I decided on December through April, mostly because the window offered the best weather in Southeast Asia. In addition, we could leverage the kids’ school holidays.
In the Spring of 2016, I wrote a letter to my school district asking for the time off (without pay of course) from my job as a high school teacher. My principal was completely supportive. So was the head of human resources. It was as if these people read my request, and wanted the same thing for themselves. They enthusiastically endorsed my plan.
Amy’s time off was a bit trickier. She is a mental health therapist in private practice. Six months out she began telling her clients that she would be gone that winter. At first, it seemed okay. But then, the election result came in, and many of her clients seemed to experience re-traumatization. Challenging.
Nevertheless, we left for the airport on December 11, 2016.
Step 3 – We planned the money.
I did some research. Major research. Meaning, I googled “How much does it cost to travel through Southeast Asia with a family?”
Turns out, there are many people who have written about this. The “Indie Traveler” site was particularly useful (see note  for web reference). Costs were reported as between $30 – $50 per day, per person, depending on the country. I budgeted about $150/day, or $20,000 total, for our family.
This turned out to be a pretty close estimate. At the end of the trip, I totaled our expenses: $19,262 for everything except flights to and from the USA (We used frequent flyer miles for those), or about $156 per day. Wow, pretty close!
How to pay?
We paid for our trip out of savings. We didn’t have the money saved before “the receipt,” but once we had committed to a dream, it was amazing how good we became at saving. For about a year and a half before we left, we examined our monthly cash flows, and took a knife to our expenses. We skipped a couple ski trips, and we cut down on restaurants. We aimed to save about $1,000/month. After a year and a half, we had about $25,000 in savings. We didn’t want to use all of our savings (an emergency fund is important), so we also pulled some money from one of our Roth IRA accounts where some stock investments had done well. Thanks to Apple and its iPhone!
Our actual travel costs
Although we tightened our belts before our trip, as travelers we lived well. We did everything we wanted to, basically without regard for cost. Of course, one’s travel style will be important here. Our style is sort of the Do-It-Yourself, but without the cooking. The major categories of expenses (listed in order of fun), were activities, food, accommodation and transport.
Activities and adventures were about one-third of the cost. Some adventures were cheap (hikes or public museums), some were expensive – our guided trek in Nepal cost $2,700 for seven days. I included some links to written up descriptions of our travel at the bottom of this post.
Food was about 20% of our budget. We ate good food every day, at restaurants or on the street. The hotter and fresher the better we discovered. We could eat on the street for about $2/meal per person. Restaurants and cafes were more – around $4-5/meal per person.
Accommodation was about 25% of the budget. We stayed in lots of different styles of accommodation, from gritty hostels to fancy hotels. Our favorites were moderately priced home stays, where nice, clean, rooms cost between $30-$50 per night. We loved the individuality, the people who ran such places, and the other travelers we met there.
Transport accounted for about 25% of the cost as well. We traveled by plane, train, bus, taxi, motorbike, tuk-tuk, song taew, long boat, bike, foot, and the back of a few trucks.
How we accessed money overseas
During our trip, we paid some for some things with a VISA card, but mostly we used cash. We took out $300 – $500 from an ATM every few days; the machine delivered local currency of Baht, Dong or Rupiah. The fees were modest, and well worth the saved hassle of needing to carry a lot of cash, travellers checks or some other method. The machines were ubiquitous in popular tourist areas. Sometimes I got a little stressed if I knew we would need a bunch of money to pay ahead. For example, at “BEES Elephant Sanctuary” (see  for link), we needed to arrive at a remote location with over $1000 for a several day experience. We planned ahead and hit the ATM a few days in a row, so it worked out. There were other issues – border crossings usually required US dollars instead of the local currency of the exiting country. If I did it again, I would have figured out how much US cash we would need, and just brought it in a hidden pocket. We could have used around $500 US total for travel visas and other miscellaneous costs.
At first I kept track of our expenses with a detailed travel budget app. But after some time, it became annoying. I just wanted to experience the time and reflect upon it; at some point even I, a spreadsheet geek, didn’t want to analyze it. However, I persisted, because I knew I wanted to write this post.
There were some US expenses that we had to cover, notably our home mortgage and health insurance. Fortunately, we found a family to live in our house. They paid for most of the mortgage payment and utilities while we were gone. Health insurance, on the other hand, was just flat-out expensive. , and we bought travel insurance. But, US-based health insurance was pricey. We paid nearly $1,200 per month for Amy’s policy and a COBRA policy from teaching for the kids and me. Ouch. Luckily we didn’t need to use it for any real ouches. We did not want to skimp on keeping access to good health care.
Here are a few things that I learned about medical care and health insurance.
Medical care overseas was excellent. We went to a doctor or other medical provider several times on our trip, and we received excellent care each time. The needs were minor, so we just paid for it. Total expenses for three visits: about $100 including some prescription costs.
Travel insurance. Travel insurance was relatively inexpensive – about $150/month for the entire family . We wanted it in case we needed emergency evacuation. Travel insurance companies specialize in working with systems overseas. We never needed it, but well worth the peace of mind.
Our US-based health insurance. We decided to keep our US-based health insurance while we were gone, in case we needed to come back to the US for care. Fortunately we never needed to. Although very expensive (we paid about $1,200/month for our family), we would not have done anything differently. We wanted to keep access to a medical system we know and trust. That said, the manner we kept US health insurance was a little clunky, and we probably could have done it better. Amy has her own plan as a self-employed person. We just kept paying the ~$350/month. That was fine. The kids and I are on a plan offered through my employer (Bellingham School District). I was informed that I could sign up for COBRA. I did, and it cost about $900/month. What I did not realize was the “COBRA” is considered a new plan. So deductibles and maximum out-of-pocket expenses reset. Even though the health insurance was the same exact plan, with the same exact benefits, offered through the same exact provider, and I paid the same exact premiums, we ended up with a “reset” on deductibles and maximum out-of-pocket expenses twice in 2017, once when COBRA kicked in, and once when we switched back to my non-COBRA plan (when the 2017-18 school year began). Grrrrrr. Next time, I will research this a bit better. There are bound to be more economical options than what we did.
Step 4 – We figured out school for the kids
For many families around the world, leaving school for four months is difficult. Some European citizens are even assessed fines for for taking their kids out of school. As a teacher, I know how difficult it can be for a student to be gone from school for an extended period. Fortunately for us, the US school system is more lenient. Officially, we un-enrolled the kids from school. That turned out to be pretty easy, though Mia lost much of her electronic cloud-based work in OneDrive when her account was deleted.
Our kids’ teachers were incredibly supportive. Porter’s 4th grade teachers, in particular, were hugely helpful. The amazing Ms. Herndon prepared four months’ worth of math curriculum for us to take as home school along the way, arranged in travel-friendly packets including assessments!
At first, I didn’t intend to do much formal home school. We used challenges like, “You have $10 US to go buy a gift from this Indonesian market for your secret santa person. How much Rupiah is that, and go buy something.” The kids loved that sort of thing.
Here is a youtube link to Porter carrying out some “homeschool travel math.”
After a couple months on the road, we could tell that the kids needed some structure. So, we designated a couple days a week as “home school days.” The kids would be required to do some math and some writing, plus another activity they don’t do on their own. Mia would be required to do some sort of PE, while Porter would read. We started doing some more formal math lessons and practiced using the supplied curriculum. I really enjoyed being my own kids’ teacher, and Porter commented that he thought he was learning a lot since there was a single adult holding him accountable.
Step 5 – Plan the logistics
Amy is our travel planner. I could go on and on about how much work she did. But, this post is not about that substantial effort. In short, she planned the first 3 weeks including transport and lodging before we left. For the rest of the time, we basically figured it out as we went. We found out that with kids, we liked having places booked ahead, rather than just showing up and figuring it out. The internet is amazing for research. There are a myriad of excellent sites to find accommodation and travel. Trip Advisor and individual blogs gave us lots of third-party reviews. Generally, once a week we would sit still, preferably near a beach or pool, to plan out the next one or two weeks.
Reflect, and celebrate
Although $20,000 is a pretty big price tag, in retrospect it seems a bargain. We experienced so much, yet saw only a few other families traveling with kids. I kept asking myself, “How many families are at Disneyland right now, and how much would that trip cost?” A little more Googling finds some answers – about $1100 per day according to Hip Munk . I have nothing against Disneyland, but we lived with real elephants , we ziplined hundreds of feet over the tops of a real Gibbon-inhabited forest , and we met real people around the world . And we did it for about one-tenth the price. Just sayin’.
Links. We do not receive any compensation for externally linked websites.
 “The Indie Traveller” – A good site with lots of detailed information about costs of travel.
 Nepal trekking. Blogpost written by John Chesbrough, April 2017.
 Bees Elephant Adventure. Blogpost written by Mia Chesbrough, February 2017.
 The Gibbon Experience. Blogpost written by John Chesbrough, February 2017.
 People are People. Blogpost written by John Chesbrough, January 2017.
 World Nomads Travel Insurance. We never needed to use the services, but they got pretty good reviews. This company was fine for us, though we never needed to use their services.