Itinerary Planning 101

Posted by on Oct 3, 2012 in General Travel, Preparations | 3 Comments

At our appearance at Meet Plan Go San Francisco 2012, I’ll be one of two panelists talking about itinerary planning. Two panelists, two perspectives. Since the other panelist writes a blog about traveling by the seat of her skirt, I guess that means I’ll be there to represent travelers with more of a Type A streak. I’m completely okay with that.

I’ve talked a bit about planning in prior posts, though I’ve tended to focus more on pre-planning; that is, the things you need to do to get ready to go. I haven’t talked as much about how to decide where you’ll go, which is kind of funny since I had so much fun doing it.

About six months before we were planning to leave, I printed out blank Outlook calendars for each of the months that we would likely be on the road. Then I took a pencil and, in about ten minutes, sketched out what I thought was a very rough idea of what we would do for an entire year. As it turned out, my quick, off-the-cuff notes turned out to be pretty accurate.

It helped that there were a few events that were more or less set in stone, and so I was required to plan around them. I knew that we’d be starting in South America in April, and that we’d probably limit ourselves to Argentina and Chile. I knew that we had to be back home after that leg of the trip for a good friend’s wedding. I knew (or thought I knew — more on that in a sec) that we’d be spending the summer in Africa, co-leading various adventure philanthropy expeditions in Tanzania and Malawi. I also thought I knew that Pierre would be working a grape harvest in France, so we’d need to be in Provence during September and October. And, finally, I knew that we wanted to spend the winter in warmer places, so I penciled in India, Thailand, Laos, and Tahiti for that season.

If you followed our travels, you know that we did indeed start with Argentina and Chile, that we did indeed spend the summer in Africa (just not quite in the places we’d imagined), that we did indeed spend some time in Provence (just not as long as we’d planned), and that we did indeed spend the winter in some warm places (but never made it to Laos or Tahiti). Two of the three scheduled expeditions in Africa fell through because not enough people had signed up, so instead of Malawi, we headed to Rwanda and Madagascar. It turned out that we traded our extra month in Provence for almost a month back home during Thanksgiving. And wintering in Asia eventually led us to Myanmar (Burma), a place we’d never even considered until we started our Big Adventure.

All of this helps to highlight my first major takeaway about itinerary planning: have a rough structure, but leave some room for serendipity. You should have a general sense of where you might end up, and ideally you should have some absolutes set up along the way, which you can then plan around as you go. This will help in budgeting both your time and your finances. That said, you should be flexible enough so that you can adapt your itinerary to accommodate the unexpected. You might meet people along the way who talk you into hitting a place that you had never even thought about (which is what happened to us with Burma). You might decide to spend several extra weeks somewhere because you love it so much, or you might want to bail early on a locale that you can’t stand.

Now, how do you even begin to form that structure? How do you decide on the places or events that will form the backbone of your trip, around which the rest of your journey will revolve? Well, this is the really fun part. My suggestion is that you make a list with three columns. In the first column, put the places that you absolutely must see, either because you’ve been dreaming of them for decades or because they are so remote that you can’t imagine you’ll ever have another opportunity to get there. (For example, for us, this column included the Taj Mahal, Easter Island, and Thai beaches.) In the second column, list places that you would really like to see, but that you can imagine being able to visit on a future trip if there’s no time on this adventure. And finally, in the third column, list places that would be nice to visit if time permits or if your plans change unexpectedly. The places in the first column will be the beginning of your trip’s backbone. Go from there.

Next, in fleshing out a more structured travel plan, there are a few vital things to keep in mind. Namely: (1) your budget; (2) the amount of time you have; (3) the weather; and (4) visa requirements. Let’s talk about these in reverse order.

  • Visas: Before you leave, research the visa requirements of every country you are even considering visiting. If you’re American, you won’t need to get a visa before arrival in most countries. In some, though, you will. (I’m looking at you, India.) Make sure you take care of those before you go. I also suggest you stock up on passport-type photos so you can get visas on the road if you need to.
  • Weather: Weather is an important consideration, but it’s not critical. Basically, I recommend that you try not to go to Mongolia in January or Bangladesh during monsoon season. But you can if you want to, and you might have an incredible time doing so.
  • Time: Everyone’s itinerary is going to vary depending on how much time they can devote to their own Big Adventure. This brings me to another major takeaway: Take your time. While we had an amazing trip, if I could change one thing I would have slowed it down a bit. I especially wish I had thought more carefully about how much time we would need for large, sometimes chaotic places like India and Madagascar, where traveling even short distances could take all day. Sometimes, in my hunger to see more stuff, I forget just how big the world is. Remember, you can’t go everywhere and you can’t see it all, no matter how hard you try or how long you have. It’s far more important to really experience and enjoy a place than it is to cover as much ground as possible.
  • Budget: Be realistic about how much you can spend, and remember that transportation will be the biggest expense on your trip. This of course means that the more far-flung your destinations and the more countries you want to see, the more expensive the trip. Long-term travelers are constantly debating the merits of round-the-world air tickets versus buy-as-you-go. Pierre and I went for the latter because we wanted flexibility to move around in more than one direction and to change our travel plans along the way. We also used lots of “discount” airlines, so the cost wasn’t as bad as we initially feared. But if you’re pretty sure about your itinerary, RTW tickets could be a good option. I’ve heard that AirTreks and Star Alliance both offer great RTW options, but can’t personally vouch for them.

And really, that’s about all the wisdom I’ve got. At the end of the day, this is your own adventure to choose. If you’re a meticulous planner, then plan. Stock up on guidebooks and make lodging reservations now. If you prefer to be spontaneous, go for it. Throw some flip-flops and a toothbrush in your bag and hit the road. But no matter what, don’t stress too much about whether you’re planning the right way. If you’ve got a ticket and a backpack, you’re doing something right. I promise.


  1. KittenCat
    October 4, 2012

    Really well written / well-thought out … Thanks :D

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