How To Plan For A Long (A Very Long) Trip

by Brenna Holeman


Flying over Portugal

People often ask me how I plan for the trips I take. Since April of 2006, I have taken 21 international trips that range from one week to nine months, spanning 61 countries. That does not include the dozens of times I took domestic trips (when living in Osaka I went to Tokyo numerous times, for example). That is a lot of planning, a lot of booking flights and trains and buses, a lot of sorting out accommodation, and a lot of thinking about just how many dresses I should pack. Some of these trips have spread across multiple countries and continents, with varying temperatures, cultures, and currencies. Most recently, for my week to Cuba, I didn’t do much more than research flight and hotel packages to Havana and buy a Cuba guidebook that I perused in the bathtub a few times. I packed the night before, after bringing my summer clothes up from the basement a few days earlier. That was all I needed to do, and I was totally happy with the way the trip turned out.

Planning a large expedition, however, requires a lot more. There are simply more facets to deal with; with each week of travel added to your itinerary, more thought is needed into how your journey will come to fruition. The biggest piece of advice I can bestow upon anyone frazzled at the thought of planning a huge adventure or round-the-world trip is this: don’t worry. Don’t plan too much; it will all come together in the end. In my experience, focus on planning the forest, not the trees. Have an idea of the big picture (where you generally want to go, things you’d like to accomplish, and what requirements you will need) but let the smaller details unfold organically. There is no way you can anticipate what you might feel like doing on any given day, nor can you anticipate what obstacles might be thrown in your path, so there is no point obsessing over the day-to-day stuff.

Here then, is how to plan the forest.


Koh Lanta, Thailand

1. Pick a date you want to leave, and research the cheapest way you can get to your first destination. It’s a common saying, but it’s true that half the battle is actually deciding to go. With an actual date of departure on the calendar, you will have the motivation to get everything else done. Research early and research a lot; there are dozens of deals online that allow for cheap international travel. I have used Flight Center on numerous occasions, most recently to book my flight from Japan to China in 2010 and for fairly reasonable flights to Thailand in 2011. It is worth it to talk to a travel agent and see what kind of deals you can get; my agent at Flight Center was able to find me a good deal to Thailand that allowed for a five-day stopover in Hong Kong. As soon as you find that cheap flight, book it. Don’t hesitate, as the price may change or you may convince yourself to put it off. Just do it.

2. Research whatever visas and other requirements you may need to enter the countries you’re interested in. I failed to do this in 2010, and was in tears on the phone with the Indian Embassy in Canada in early 2011 (though some quick research online calmed my nerves when I learned I could get the visa in Bangkok). I’ve also heard horror stories of people being turned away at the airport for not having ongoing tickets or the proper paperwork to enter. Do not trust anybody else for the answers; find out what you need from a direct source – I recommend checking your guidebook, searching online, and even calling embassies. I was told by my Japanese travel agent in 2009 that I didn’t need a visa for Vietnam, and, trusting her, didn’t get one. I was livid when I had to call in sick to work the day before leaving for Hanoi just so I could obtain the visa that I did in fact need. Also check for any immunizations you may need (for example, a yellow fever shot is required to enter some South American countries).

3. Buy a guidebook and start a travel notebook. There are those who don’t believe in taking guidebooks, but I consider my guidebooks my bibles. Not only are they great when you are actually in the country, they are wonderful to flip through ahead of time to find out vital information and to help shape your trip. I try to devote a few minutes every day to reading a small section, looking at maps, and taking a few notes; I highlight important points, write down cities and towns that interest me, trace possible routes, and circle hostels that look appealing. While you aren’t setting anything in stone, it’s good to familiarize yourself with some of the places you may visit in the future.


With my trusty guidebook in Yangon, Myanmar

4. Start to wrap up your home life. Start this as soon as possible. If you need to pack up your apartment, for example, begin this weeks if not months before you have to leave. Make sure bills will be looked after, services (such as internet or cable) will be stopped, storage for your car or your belongings is settled, etc. Whatever it is you have to do before you leave to ensure your home and your things will be taken care of, do it immediately. The last thing you want to be thinking about the day of your departure is who will water your plants while you’re gone.

5. Start packing. NOW. OK, maybe not this instant, but start thinking about exactly what you will need on your adventure. Will you need an extra camera battery? Buy it immediately. Do you have an idea of what clothing you will bring? Take it all out of your closet and try it all on, even if you aren’t leaving for months. Are there a few things you know you’ll need to get (i.e. a first aid kit, travel towel, or alarm clock)? Make a point of picking these things up as soon as possible. The more you do ahead of time, the less stressed you will be when it comes to actually packing. You don’t want to be rushing around three days before you leave trying to find a good pair of walking shoes, or realizing you don’t have photocopies of your passport and visas as you’re on your way to the airport. Write down everything you will need to purchase, do, and pack, and get it all done long before your departure day arrives. I’ll be posting my packing list/to-do list for my upcoming adventure in the next week or so.

6. Finally, book the first few days/weeks of your trip. While I have always been a fly-by-the-seat-of-my-skirt kind of girl, I never arrive on day one with absolutely nowhere to go or nowhere to stay. I always book my first few nights of accommodation (minimum) and have a good idea of where I’m headed and how I will need to get there. I also have some of the local currency for the first country I’ll be in and/or the country I think I’ll be in the most. I often use Hostelworld to help me out, and I’m always checking the Lonely Planet forums for advice on train schedules and such. To give you an example of this, when I arrived in Bangkok last year, at the start of an 8-month trip, I had a hostel booked for three nights, and that’s it. From prior research, however, I knew what bus I wanted to take to get to Koh Lanta, the phone number of the guesthouse I wanted to stay in, and a rough idea of the islands I would hit in the following month. I had a good idea of what I was going to do, but I was open to change and open to the fact that something (or someone) might come along and make me want to totally scrap that plan.


On the bus in Thailand

So there you have it. That is how I plan for any trip longer than a couple of weeks. I always end up changing my itinerary as I travel and so booking accommodation, flights (other than the first flight), or activities too far in advance just doesn’t work for me (for example, check out my original plan for 2011 here, and then compare that to what I actually did here). The idea of seeing where the wind takes you doesn’t always work, of course; Southeast Asia is a backpacker’s heaven, and it’s so easy to travel without an itinerary there. When travelling through Russia, on the other hand, I needed to have everything planned to the day. You’ll obviously have to figure out what kind of place you’re travelling to and plan accordingly, but in general, and in my opinion, you can travel quite easily without a set itinerary through Southeast Asia, India and Nepal, most of Europe, Central and South America, North America, and Australia and New Zealand. Eastern Europe, the Middle East, Central Asia, Africa, Antarctica, and anywhere really off the beaten track requires a bit more planning.

Despite all of this advice, I know, without fail, that I will be scrambling in those last few days before I leave for Central and South America (check back here for 3am posts and stress-filled rants from April 27th to May 2nd). Short of completing the things on this list, charging my camera batteries, and getting a spray tan (Belize ain’t ready for these pasty white thighs), there’s not much more I can do.

Do you think I’ve missed anything? What else do you do before heading on a big trip?

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MacKenzie April 16, 2012 - 11:54 pm

What do you do about money? I know you said you bring some cash, but what do you do about money the rest of the time? Can you use a debit/credit card overseas to get cash? I’ve been wondering about it for a while and figured you’d definitely know! 🙂

This Battered Suitcase April 17, 2012 - 12:19 am

Hi MacKenzie! I bring both a bank card and a credit card when I travel, and I’ve never had a problem getting cash while abroad. In general, my Canadian cards work just fine with international ATMs. I had a bit of trouble with my debit card in certain countries (Japan, Cuba, and India spring to mind) but I was always able to use my credit cards or get cash advances on my credit card in those cases. Just make sure to alert your bank that you’ll be out of the country!

Audrey | That Backpacker April 17, 2012 - 12:28 am

I like how you worded it ‘plan the forest but not the trees’. I’ve learned it’s best to have a general idea of what you want to see/do, but let the details fall into place once you’re actually there. You just never know who you may meet or what the weather may be like, so last minute is often the way to go! 😀

Andi of My Beautiful Adventures April 17, 2012 - 2:01 pm

Great tips dear! Love the currency shot.

This Battered Suitcase April 18, 2012 - 12:21 am

Audrey – I totally agree! I like having a general plan (and knowing when it is necessary to book ahead of time), but I really like just going with the flow.

Andi – Thank you very much!

Ekua April 19, 2012 - 1:53 am

Very useful post! Question – what do you typically do with your stuff when you go? Put it in storage?

This Battered Suitcase April 19, 2012 - 5:12 am

Ekua – I have put things in storage in the past, but this time I’ll be storing everything in the basement of the house I purchased last year. I also have things in storage at my dad’s house! I generally have possessions scattered all over the world…

Flights to Lagos July 12, 2012 - 2:42 pm

All travel is circular. I had been jerked through Asia, making a parabola on one of the planet’s hemispheres. After all, the grand tour is just the inspired man’s way of heading home. Cheap Flights to Lagos

crystal watson October 22, 2012 - 8:52 am

“We should come home from adventures, and perils, and discoveries every day with new experience and character” – Henry David Thoreau

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Stephina Suzzane November 19, 2012 - 10:14 am

I travel a lot; I hate having my life disrupted by routine.

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How To Plan a Trip (That Actually Needs to Be Planned) - This Battered Suitcase December 6, 2013 - 1:22 pm

[…] How to Plan For a Long (A Very Long) Trip […]

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[…] tied up any loose ends. I talk about this in the post How to Plan For a Very Long Trip (which you might want to read if you are indeed thinking of long-term travel). If you are planning […]

Tara March 20, 2017 - 10:04 pm

Loving your blog Brenna!

Brenna Holeman March 21, 2017 - 1:28 am

Thank you, Tara! 🙂

Christian May 30, 2022 - 2:36 pm

Amidst planning a RTW year long trip, how many countries is too many countries?


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