How We Planned Trekking the Planet

Darren goes behind the scenes to show how we planned our extended journey.

One of the most frequently asked questions we receive when we are out speaking with students is, “How did you plan such a long trip? “ Whether you are just curious about how we did it or dream of some day taking your own extended journey, we hope that this article at least partially “lifts the veil” on the process that we followed.


Before we get into the nuts and bolts of the process we followed, a little background might be helpful. We are planners. We like to have our reservations in place before we leave. We like to know where we are going and what we are doing. For this particular journey, there is another reason why we decided to plan this trip so carefully. It is our commitment to send out our education modules each week that we are traveling. If we did not know our itinerary, we would not be able to do the education module research before we left and would have to spend valuable time during the trip producing them.

So what were the steps that we followed when planning Trekking the Planet?

Step One: Come up with the Theme

The biggest danger in planning a long journey is getting bogged down in the details too soon in the process. Thus, we took an iterative approach to planning the trip. This means that we started at the highest level and came up with the theme of the journey. The theme we selected was, of course, “trekking”. However, because of the length of our expedition and the other things that we wanted to accomplish, we included the additional themes of “education”, “geography” and “on the ground travel”. These themes formed the lens that we used to evaluate destinations during the planning process.

Step Two: Come up with the Goals

Based on the themes above, we then came up with a series of goals for the trip, including:

  1. Trek to some of the most remote and unspoiled places in the world
  2. Visit at least 50 countries on six continents
  3. Limit air travel as much as possible
  4. Use our trip as a way to help students learn more about geography

Looking back, we feel that the value of the “theme-then-goal approach” is that it reduced the number of possible travel combinations. This technique helped us to stay on track.

Step Three: Build the Framework

Using the themes and goals from the prior two steps, we started building our high-level plan. The first problem that we focused on was how to get to each continent without flying. Since we had a positive past experience with Princess Cruises, we decided to start there and review their cruise schedule. We focused most of our attention on so-called “repositioning cruises” (used by the cruise line to shift their ships and crew to a new location at the end of a given cruising season). At the conclusion of this step, we had a 424-day itinerary which listed each of the cruises we planned to take. Of course, there were huge chunks of the trip that were completely unplanned, but this step gave us the framework for the rest of the planning process. Our high-level framework plan at the end of this step was:

  • San Diego, U.S.A. – Sydney, Australia (Cruise #1)
  • Sydney, Australia – Singapore (Cruise #2)
  • Singapore – Asia – Europe – Africa – Rome, Italy (Mainly overland)
  • Rome, Italy – Fort Lauderdale, U.S.A. – Manaus, Brazil (Cruises #3 and #4)
  • South America (Mainly overland)
  • Santiago, Chile – Los Angeles, U.S.A. (Cruise #5)

Step Four: Locate Interesting Destinations

For the next step, we purchased a large map of the world. We mounted it on a piece of cardboard and started to add push pins. Each push pin represented a destination of interest. Since we selected “trekking” as our major theme, we focused there during this phase of the planning process. Using the Internet, we searched on terms such as “Top 10 Hikes in the World”. With a spreadsheet, we captured the country, number of days, best months to visit and a rough approximation of cost. At the end of this step, we had the second version of our itinerary that included not only the transportation between the continents, but also some of the places we wanted to visit in between.

Step Five: Fill in the Gaps

Because one of our goals was to help students learn more about geography, we started writing education modules. For example, we knew we would be visiting Hawaii on our trip. We developed a four-page template for the modules that covered the human and physical geography of each place. Since we are not teachers, we wanted to provide an easy-to-use resource that could be used as a “jumping off point” for classroom discussion.

Note: You can view the Hawaii Education Module and sign up to receive other education modules here.

Developing these initial education modules helped us to uncover more destinations to fill the gaps. As this occurred, we added more push pins to our world map and updated our list. We used the Internet and guide books for our research, favoring the Lonely Planet guides. Eventually, we attempted to string all of the destinations on our map together. The output of this exercise was our first high-level itinerary!

Step Six: Build the Detailed Itinerary

At this point, problems started to arise. Even with all the previous work, the sheer numbers of possible combinations made our heads spin. That is when we realized that planning a long trip is exactly like planning a series of shorter trips, each one starting where the last one left off. By focusing our attention on only one portion of the journey at a time, we found that it made it more manageable. We also divided up portions of the expedition to plan. Darren took Central Asia and Africa and Sandy took Australia and Europe. This worked for awhile. However, the process started to break down as the numbers of tasks became daunting.

We then adopted another technique which helped even more. We wrote each task on a Post-It Note. At the beginning of each week, we stuck all of the notes that we wanted to complete that week on the back of one of the double doors in our guest bedroom. As we completed tasks, we moved the corresponding Post-It Note to the other door. If we came up with a new task, we restrained ourselves from doing it right away, and instead wrote it down on a new Post-It Note. These we put on the mirrored closet door in the same room, to be re-prioritized with the other remaining tasks at the beginning of the next week. The outcome of each week was a set of completed tasks and a new, better-developed itinerary.

Step Seven: Book our Reservations

Once we felt we had a solid itinerary for the full 424-days, we started to book hotels and contact guides for some of the more remote trekking destinations. As we moved from the early part of our trip, we started to hit what we now call the “planning horizon”. For us it is the absolute furthest out that we can make reservations. Our planning horizon for this journey was out to six to nine months. Beyond that, guides and hotels did not know their availability or their prices. To work around this, we still built the day-by-day schedule, but instead of booking everything, we created tasks for those items further out. At this point, we have the first 11 months 90% booked. We have left the reservations in South America open. This is something that we plan to accomplish while on the trip.

Step Eight: Wrap it Up

One of the last steps in the process that we followed was to take another pass through the itinerary, adding the actual amounts we have booked and deposited, along with those that remain to be paid. This allows us to monitor our spending as we go, comparing “actual” to “budget”. We used a program called PrimoPDF to archive all of our receipts and email exchanges and stored them using a cloud service called Dropbox. In addition to the itinerary, we have built another document we call the “Week by Week Plan”, which captures destination details (such as how to get from the train station to the hotel using public transportation), as well as listing those tasks that could not be completed before we left.


It would be naïve to think that we will be able to stick to our plan for the entire journey. It is inevitable that we will need to re-plan parts of the trip, either because we are delayed or because, for some reason, we cannot go somewhere we planned to go. This is where we can go back to earlier versions of our itinerary and grab something that was thrown out because it would not fit in at the time. When we purchased guide books, we bought the PDF versions, so we will have access to these as needed. Finally, with few exceptions, we booked hotels that would refund our deposit if we need to change or cancel our reservations. This way, we can remain flexible if things change.

Note: If you have a question or comment after reading this article, feel free to add it to the Comment Box found below.

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3 thoughts on “How We Planned Trekking the Planet

  1. Shirley Wooldridge Reply

    All I can say is “Wow!” What an adventure. Sandy, I know you have a mother is extremely organized and I believe you inherited that trait!

  2. Pam Blanchard Reply

    This is a fantastic idea. I’m looking forward to following you along with my students. Thank you!

  3. Hannah D Reply

    Your adventure is going to be incredible! I think planning a lot ahead of time (though leaving wiggle room) is a fantastic idea as you are unlikely to find yourselves in any kind of hot water on your travels. I’m really looking forward to reading your end-of-week round ups. This is going to be a learning curve all round! It’s so close to your departure now – have fun!

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