Planning a multi-country overland trip (Part 2)

This is Part 2 of this post, detailing the Imagine and Prototype stages of our trip planning. Read Part 1 here.


This is the time to start thinking of the places you want to visit, the languages you might want to learn, the activities you want to do, and, of course, the places you want to visit.

You might think this is easy and straightforward. But, as my first big trip highlights, it is not always that simple. I fully expected my first big trip to be to Asia. I had even put my foot in Asian waters with short trips to Myanmar and Sri Lanka. However, circumstances meant I went to the Americas.

The key to imagining how your trip might pan out is to brainstorm and affinity map. There is an art to successful brainstorming and it is worth developing a few mindsets to get this right.

  • Defer judgment. Put your ideas out there without judging them.
  • Build on the ideas of your travel partners using the “yes, and” protocol (For example, “I want to see orangutans in Borneo”. “Yes, and while we are there we can see proboscis monkeys and climb Mt. Kinabalu”)
  • Go for quantity and a diversity of ideas (get all your ideas out there)
  • Be wild (Really, get ALL your crazy thoughts down. Don’t discount anything yet)
  • Use “How might we?” to try and keep ideas alive (For example, “How might we go to Afghanistan?” The answer here is that you can travel safely in the Wakhan Corridor by crossing the border from Tajikistan!)

Now, grab a bunch of post-it notes and a pen and throw down some ideas using the above mindsets.

Once you have finished, look for ideas that are variations on a theme and put them together. This is called affinity mapping.

Once we had brainstormed we came up with the following (this is the abridged version!):

  • Silk Road Route (The ‘Stans, Xinjiang)
  • Caucasus (Armenia, Georgia, Azerbaijan)
  • Indonesia
  • Vanuatu
  • South Asia (India, Nepal, Bangladesh, Sri Lanka)
  • SE Asia (Burma, Laos, Vietnam, Singapore, Malaysia, Cambodia)
  • Papua New Guinea
  • Hiking (Everest Base Camp, Fan Mountains, Pamirs, Tien Shan, Arslanbob)
  • See orangutans, proboscis monkeys, and hornbills
  • Baliem Valley festival in West Papua
  • Create travel apps (Travel budgeting, Photo app)
  • Yurt stays (Kyrgyzstan, Tajikistan)
  • Visit friends and family (UK, Alaska, Australia & New Zealand)
  • Angkor
  • Borobodur
  • Pamir Highway
  • See and climb volcanoes
  • Jungles, wildlife

We also had smaller affinity maps for South America and Africa. We quickly discounted South America for this trip since I had already visited many of the countries and attempting to visit it as well as Asia would be unfeasible in our time frame. Africa is in our plans for someday but there was less immediate “need” to go.

We then created our first “prototype” itinerary.


A prototype helps you:

  • Create a representation of your ideas
  • Test your ideas
  • Make your ideas “come to life”
  • Test various variables
  • Get feedback
  • Fail & learn fast without spending a penny

A prototype for a travel plan is an itinerary. We took a large calendar and started to plot a route.

A key idea here is to start to think in terms of constraints. Constraints can be time, money, seasons/climate, or red lines (things you cannot leave out). Other constraints can be out of your control such as limits on the time a country allows you to stay.

From our immersion phase we knew the best times of year for visiting various places so we plotted our itinerary in terms of best times to visit (for example, to avoid monsoon season and to be able to hike in high altitude mountain ranges). We knew that Indonesia and Central Asia were must-dos. We also knew that both areas have ideal weather conditions in summer. This gave us one constraint- the trip would have to last at least two summers to do justice to both areas.

Other constraints were events that had time limitations, for example, the Baliem festival in West Papua happens every August. We also gave ourselves a dollar constraint for the whole trip so that we could work to a daily limit. Some areas are budget busting such as visiting Iran (Americans and Brits must take a guided tour, which is much more expensive than traveling independently), but other areas we know will come way under, such as India.

Once we had the first prototype we started to put it to the test. There were two possible routes: roughly West to East (starting in Turkey) or East to West (starting in Vanuatu). However, we realized early on that there were difficulties in lining up Uzbek, Turkmen & Chinese visas on the road. We also realized once we had a first prototype that Iran was a possibility too. Iranian visas would be extremely tricky to arrange on the road so we decided to go West-East so that we could deal with complex visa issues from home before departure.

The Caucasus was dropped early too since the best season to visit was the same time as Central Asia. We continued in this fashion until we landed on an itinerary that was logistically feasible, affordable, and hit the countries in optimal seasons. Since we didn’t want to fly much it was really important to us to have an itinerary that was feasible overland.

Our prototype changed daily as we learned more.

We also knew from our prototype and affinity mapping that hiking was a major activity and so we had to pack accordingly. I will blog later about what to pack and how we came to our decisions.

We ended up with a final prototype to put to the test and to start preparing for. We fully expect this to change. In light of the tragic earthquake in Nepal, we have already put our trip to Everest basecamp on hold. As I write, we are investigating the possibility of replacing Nepal with New Zealand for our hiking fix. One downside of this is that we will have to fly there and back from Southeast Asia, which somewhat violates our eco and overland rules.

Once we were happy with our plan we created a kanban (a prioritized to-do list in a to-do, doing, done format) with key items to arrange. Priority was based mainly on dates we needed to start or finish certain processes or activities. This included arranging the aforementioned visas, organizing tours to Iran and Turkmenistan, and booking one-way flights to our first port of call. We also put items to arrange at home on the Kanban such as storage, quitting work, and finding the best systems for handling money. The Kanban and prototypes took center place in our house for 5 months. It is easy to see what needs to be done if it is highly visible!

Our trip preparation kanban board.

The prototype will always be a work in progress and the final product will only be evident once we have finished the trip. We will continue to re-work our prototype as we get nearer to each phase of our trip. We continue to learn and modify as we go always in the knowledge that we have a solid base from which to adjust.

One thought on “Planning a multi-country overland trip (Part 2)

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

Leave a Reply

Your email address will not be published. Required fields are marked *

CommentLuv badge

This site uses Akismet to reduce spam. Learn how your comment data is processed.