Planning a multi-country overland trip (Part 1)

Paul here, posting from the courtyard of our guesthouse in Shiraz, Iran. This post was written during our two-day train and ferry journey from Ankara to Iran. We’ll post about our travels in Turkey and Iran soon. Facebook is blocked in Iran, so the earliest you’ll see us back on Facebook is when we cross into Turkmenistan on June 11.

On telling friends that Laura and I were “going traveling”, there was a persistent theme to responses: “How did you plan such a long trip?” “How did you save the money?” “What are you going to do about work?” “Have you reserved everything in advance?”

A number of friends seemed inspired to travel too but seemed to be stuck at the planning stage. So, in this blog I would like to propose an approach to planning which will hopefully help them on their way.

Answers regarding money and work were simple. Travel and hiking is what we spend our money on and this is what we primarily save for. Since we did not want to work while traveling, we quit our jobs.

Planning can be more complex to explain.

You need not plan at all which was the case on my first long trip in 1996-97. To cut a long story short, on March 29, 1996 my great travel buddy Graham Dietz, seeing that work was causing me considerable stress, invited me to join him on his upcoming trip to Central America. On March 30, I bought a one-way ticket to Mexico City; April 1 I quit work; and, on April 4 I flew out. I expected to be traveling for 6 months but stayed for 18 months. I made one visit to the doctor to update basic vaccines and grab malaria prophylaxis; the dentist fixed my teeth up; I picked up insurance, a Central America guidebook, and $20K in travelers checks; and packed a 45 liter backpack with 2 pairs of jeans, 2 shirts, 2 T-shirts, and a week’s worth of socks and undies.

Paul modeling his new wardrobe in Peru, 1997.

There was, of course, no Internet or email back then so my sources of information on the road were Lonely Planet books, fellow travelers, and travel hostels and cafes. I booked nothing in advance and everything was done on the fly. The fantastic thing about the trip was that everything had a high degree of “wow factor” since I had very little idea of what anywhere looked like aside from the odd image in LP guidebooks. These days you can do so much pre-trip research that when you reach a destination you almost feel as though you have already been there!

I genuinely went with the flow. If I met a cool bunch of people who were traveling to City X, I was happy to go along for the ride. I went to places I never expected to visit and usually it turned out great. The only downside was that I also missed out on a few classic destinations, which I now regret. For example, I didn’t go to the Galapagos citing the expense, and due to poor planning I could not visit Patagonia because it was not the season for hiking there. Poor planning also left me exposed to dangerous situations. I went on many high altitude hikes without even the basic level of decent hiking gear.

So, these days I plan a little more for a big trip. In the spirit of helping others take the plunge I want to propose an approach to planning based on Design Thinking principles I use in my day job. Design Thinking is an approach to product design that was formulated at IDEO and Stanford, and subsequently adopted by famous companies such as Apple and Nordstrom. The product we are designing in this case is your ideal travel adventure.

The core elements of design thinking are:

  • Immerse
  • Frame
  • Imagine
  • Prototype


This is the section in which you learn about the travel needs of you and your travel partner. In essence, this is the discovery phase of your planning.

Empathy is the key mindset here. It is essential that you really do understand the core needs of both of you. If you don’t, things can go horribly wrong fast on the road. For example, many years ago I went on a month long trip to Pakistan. My partner back then wanted to do a relatively easy trek in the Hunza Valley but I was obsessed with the idea of hiking to K2 basecamp- a serous undertaking in a very hostile environment. I ignored the needs of my partner and we undertook the K2 trek, which she was not really OK with. We made it to the end and I now have an amusing story about being dumped by my girlfriend at K2 basecamp! However, 9 days into a potentially hazardous, life-threatening hike is not the time to realize you should listen more, or be more empathetic.

So, know thyself and thy partner!

Laura backpacking the Enchantment Lakes in our home state of Washington. Hiking and experiencing the outdoors are priorities for us at home and on the road.

For Laura and I, after a period of immersion we know that our core travel needs are:

  • Overland (Limit flying)
  • Independent (Limit tours or packages)
  • Maximize nature, outdoors, and hiking
  • Focus on small towns and villages (Limit the visits to big cities)
  • Culture
  • New countries for both of us
  • Music/Sound
  • No party scenes or druggie hangouts
  • Eco-friendly
  • Define the scope (Not a round the world trip; focus on one or two continents)
  • Logistics (Let’s sort out the complex issues before we leave: visas, routing, climate and seasons)
  • Seek out the roads less traveled but let”s not miss out on the big hitters
  • No paid work on the road but let’s keep our skills sharp and up-to-date by building apps
  • Risk tolerance (Medium-high)
  • Budget travelers willing to make occasional splurges for must-do adventures

And, how did we come to these needs? We used whatever sources were available to us.

  • Previous travels together (I would recommend that you do a 2-3 week trip with your partner before heading out on your big trip)
  • Blogs (For example,,,, and
  • Guidebooks (Lonely Planet, Bradt, Rough Guides, Odyssey)
  • Forums (Lonely Planet Thorn Tree, Tripadvisor)
  • Friends who travel
  • Travel agents in various countries
  • TV (BBC Nature Films, Globetrekker)
  • Look at blogs from a variety of different views: extreme travelers; female travelers; people who earn money through travel; non-Western travelers

While researching, we found it essential to have the following mindsets:

  • Be curious (dig deep so that you really understand the places you might want to travel)
  • Challenge assumptions (Are Iranians hostile to Americans? Answer- no!)
  • Watch for surprise reactions from your partner (Don’t presume what your partner’s needs are)


Using the needs identified above, you can frame the type of travelers you are and the opportunities that seem applicable to you.

Why would you do this? To give you an easy frame of reference to figure out whether the trip you eventually plan for you is reflective of your actual travel needs. For example, if Laura and I put together a plan that consisted of flying visits to Bangkok, Jakarta, Kuala Lumpur, Ko Phang Nga, Koh Samui, Bali, and featured no hiking then we are violating our needs to avoid big cities & party places, be eco-friendly and hike a lot!

In my Pakistan story, in hindsight, I recall our joint needs being to hike in high mountain terrain in Asia during my college summer recess. I violated the joint needs by focusing on my solution alone.

So, how do we keep the frame of reference in the forefront of our plans? By creating a “problem statement” or “point of view statement”. This will help you focus on your ideal trip as you move towards the Imagine phase. The key here is hitting the sweet spot. You don’t want a POV that is too broad or too narrow. For example:

“How might Paul and Laura travel during a career break in a way that we see lots of stuff?”

This is way too broad. Everything is an option still!

“How might a career-breaking Paul and Laura hike in Nepal and Kyrgyzstan in a way that they see lots of yurt dwellers?”

This is way too narrow! What about the culture, app building, and visiting new countries (We have both already been to Nepal and Kyrgyzstan)? Not too mention the fact that we have already defined the area too early!

“How might independent-minded, big city-phobic, eco-friendly, outdoor-obsessed, culture-vultures, Paul & Laura, travel in a way that maximizes exposure to new places, is challenging, budget aware but not limiting, and creates opportunities to sharpen skills in readiness for future work?”

This is a good starting point! It has kept our options open in terms of places but has narrowed the focus in terms of needs.

It also helps you to be honest with yourself. In the past, I have indulged in adventures that were really outside of my comfort zone. Lots of people dream about climbing Kilimanjaro or Mount Kinabalu and spend lots of money attempting these and failing! If you really do want to do stuff outside of your comfort zone, if it is clear in your POV, then you know you have some pre-trip preparations!!

The key mindsets for Framing are:

  • How might we []?
  • Honesty

See Part 2 of this post for the Imagine and Prototype phases of our trip planning.

5 thoughts on “Planning a multi-country overland trip (Part 1)

  1. Pingback: Planning a multi-country overland trip (Part 2) | Design Think Travel

  2. Amy Lane

    Wonderful topic, great idea to break it all down. Mike was just asking about you last night! Missing your perspectives back here!

    1. Laura

      We took antimalarials for Sulawesi and again for Myanmar. We use doxycyxline because that is what is available in SE Asia. The downside of doxycyxline is that you have to keep taking it for four weeks after leaving the malarial area. There is a lot of conflicting information out there about the need for antimalarials. Doctors might tell you that you need to take them almost everywhere in Asia, but not many travelers seem to be taking them. My preference is to not take them except for known malarial areas, and to avoid mosquito bites by wearing long pants and repellent in the evenings.


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