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How to: A Long-Term Travel Planning Checklist

Arthur Worsley
by Arthur Worsley
M.A. Psychology, Oxford. McKinsey Alum. Founder & Editor at TAoL.

Perfect for you if:

  • You’re travelling to learn and experience as much as possible.
  • You want to plan a big trip independently but have no idea where to start.
  • You often find yourself finding out all the great stuff you missed after you leave.

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“In preparing for battle I have always found that plans are useless, but planning is indispensable.” Dwight D. Eisenhower

There’s an infinite number of ways to go about travel planning, or even not to go about it at all – and this post is not about trying to convince you either way.

Instead, it’s just an insight into my own system of travel planning that’s evolved from the last few years and ~70 countries of travel blunders as well as the kind and patient help and advice of hundreds of fellow travellers and travel buddies along the way. (N.b., I travel with pretty much exactly the same set up in my trusty 40 litre backpack no matter where I’m going so packing doesn’t feature here! More in another post.)

I won’t always follow every step exactly (or at all), and the effort I put into each plan really depends on the country I’m travelling to, the way I’m travelling and also how travelled or planned-out I’m feeling (in fact giving up on planning is a good indicator that it’s time for me to stop, settle down and recharge).

But so far I’ve found, aside from getting more out of my time and money in each country, that it’s only when I have a solid back up plan in my back pocket (as well as the knowledge in my head that it took to put it together) that I’m able to totally relax, tear it up and travel most spontaneously when opportunity comes knocking!

The top section that follows is just the raw checklist but click on the orange header links at the top of each section for more detail.

Region/Country Level Planning

1. Define success
☐ Write a why statement (bullets)
☐ Visualize success (bullets)

2. Identify barriers
☐ Visa requirements
☐ Festivals / holidays
☐ Health / safety risks
☐ Weather (seasonal, regional)

3. Download or gather links to travel information
☐ CIA World Fact Book
☐ Lonely Planet
☐ Wikipedia
☐ Wikitravel / Wikivoyage
☐ Top 10 lists (Google)
☐ Itineraries (Google)

4. Do background reading
☐ Lonely Planet (esp. back section)
☐ Wikipedia
☐ Wikitravel
☐ Other

5. Synthesise a “Top 10” list
☐ Friends / Travel Buddies
☐ Lonely Planet
☐ Wikitravel / Wikivoyage
☐ TripAdvisor
☐ “Top 10” lists (Google)

6. Plot “Top 10” list on Google MyMaps

7. Draft an itinerary
☐ Draft a rough itinerary
☐ Check vs. 3rd party itineraries
☐ Check vs. success statements

8. Firm up itinerary
☐ Research travel options/times between locations
☐ Check transport, ticket and accommodation availability
☐ Calendarise itinerary

9. Refine as you go
☐ Update the plan based on:
Location Level Planning; and
→ On the ground information
★ N.b., Don’t let the plan get in the way of the trip

10. Look back on the trip
☐ What did I do? What didn’t I do?
☐ What did I learn? What was surprising?
☐ What went well? What would I do differently?

Location Level Planning

1. Repeat steps 3 – 6 from country-level planning

2. Finalise and book accommodation and logistics
☐ Book accommodation
☐ Book inward / outward travel

3. Download local resources offline to iPhone
☐ Google maps
☐ Ulman maps
☐ TripAdvisor

3. Check travel and accommodation calendar entry notes complete

Sight/Activity Level Research

For each major sight/activity repeat steps 3 – 4 of country planning

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1. Define success

Write a Why Statement:

Why: Really helps me prioritise effectively between options before and during the trip by surfacing my real motives for visiting a country.

What: Anything from a few bullet points to a wordy treatise, whatever I need to get clear in my head.

How: I whip out a pen and paper and jot down the first few answers that come to my head to the question “Why do I want to travel to X?”.

For example: Because I’m fascinated by a particular aspect of history/culture, because I don’t know anything about it, because I’m afraid of it, because seeing X or doing Y is on my bucket list, because I need a break and I just want to relax or even just because it sounds awesome!

Visualise Success:

Why: Helps turn the Why Statement into tangible goals/outcomes that I can begin to plan around.

What: Usually no more than 5 or 10 tangible goals / outcomes that would make the trip a success.

How: Back to pen and paper. What would it take for me to look back on this trip and go “Boy, that was an incredible experience, I’m glad I did that!”

For example: I visit, try, learn, taste, meet, master, feel etc… X, Y and/or Z.

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2. Identify barriers

Why: Because turning up to hike in rainy season, straying into a war zone, catching malaria or arriving in Ho Chi Minh city on the first day of Vietnamese New Year (when everything is shut for a week) all suck (and are easily avoidable with some quick research).

What: Visa issues, weather and disruptive festivals / holidays are the big things I look out for. I’m a bit more relaxed on health and safety – I’ve spent amazing weeks in e.g., Guatemala or the Northern Border or Afghanistan when government websites would have you believe you’ll be shot or kidnapped the moment you cross the border.

How: There are tons of resources so Google is my friend here, especially for really local or more unusual trips (like overland travel). I’ll always preference recent accounts of e.g., border crossings from other travellers over official government websites.

For Visas I’m a big fan of VisaHQ. For weather check out Best Time to Go. For health risks / vaccinations see IAMAT.

If you really want to unnecessarily terrify yourself then ask the U.S., Government for its opinion on anywhere else.

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3. Download or gather links to travel information

Why: Because having these to hand or making them available offline makes it easier (and so more likely) that I’ll read them in the little 5 – 10 minute gaps that crop up in my day or to refer to on the road.

What: There’s a host of great travel information websites on the internet. Here are my go to sources…

CIA World Fact Book – updated annually and full of amazingly detailed facts and statistics for almost every country in the world.

Lonely Planet – is my personal go-to brand of guide books for travel, I buy the PDFs from their online store and especially love the front (top lists, itinerary ideas) and back (cultural and historical overview) sections of their books. Other major options I know of include Rough Guides, DK Eyewitness Travel Guides and Marco Polo Pocket Guides. There are also some great alternative if you speak other languages (especially German).

Wikipedia – has been my first point of call for mostly accurate information as long as I can remember

Wikitravel / Wikivoyage – despite being more prone to error than Wikipedia, these sources usually have a more digestible overview and lots of practical advice (like how to travel to/within the place you’re visiting). Their content is mostly duplicated these so I’ll pick one or both.

Top 10 lists (Google) – Travel blogs and travel agent websites are a wealth of information. I’ll spend a few minutes on Google searching for things like “top sights in” or “best undiscovered secrets of” and pick one or two of the best for more reading.

Itineraries (Google) – As above for “X weeks in Y” or simply “Y travel itineraries”. I find the websites of high end travel agents like Audley Travel perfect for this.

How: I’ll usually save these down as PDFs to a folder in my DropBox. In Safari on a Mac I prefer to Print (File > Print or Command + P) and then save as a PDF (bottom left corner of print dialogue). I don’t know why, my gut tells me I’ve found the built in export function a bit dodgy.

Bonus: If you have a Mac, this little location info script quickly opens four tabs in Safari for the Wikis and Trip Advisor for any location you input.

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4. Do background reading

Why: Learning about the country and putting it into a little bit more context (historically and geographically) totally transforms the experience of travelling for me. Not only does it help with the planning stage but it gives my mind lots of hooks to hang my experiences on when I’m there and primes me to look our for and understand things I might otherwise totally miss.

What: Most of the information gathered so far.

How: Just a quick skim through over everything to give myself a feeling for the country at this stage. As I learn more about my target destination I’ll usually be frequently revisiting and updating my Why and Success statements to reflect any new learnings and ideas.

N.B., I really like to revisit this information when I can during and at the end of my travels – it’s amazing the different things that stand out from the text at each different stage depending on the things I’ve seen and experiences I’m having.

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5. Synthesise a “Top 10” list

Why: Even if I tear up my plan or do something totally different, having this list subconsciously in the back of my mind is great for spotting and taking advantage of opportunities to get at it.

What: Usually many more than just 10 places I’d like to see and experiences I’d like to have. My risk of “box ticking” (just visiting a place because I “should”) is much lower if I’ve done the first few sections of this checklist properly – a list without some decent Whys behind it always feels shallow and uninspiring to me.

How: Pen and paper or a text file on my computer.

An amazing additional source for these are local friends and fellow travellers. A good friend of mine had the great idea of asking friends she makes on the road for their top local recommendations for wherever they’re from. Then she saves/stars these locations on Google Maps. When she arrives in the country she already has hundreds of local-only sights, restaurants and experiences to hand!

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6. Plot “Top 10” list on Google MyMaps

Why: Seeing everything I want to do laid out on a map is an incredibly powerful clarifying experience for me. It suddenly makes distances very real as well as highlighting interesting facts like “Oh, 90% of the things I want to see and do are over here”, “So seeing that means a 900 km detour to the West” or even prompting questions like “I wonder what’s over there?”.

What: Here’s an example of 3 Days in Tokyo (also below) or a basic “Top List” dump of Taiwan

3 Days in Tokyo: Google MyMaps
Three days in Tokyo, planned on Google MyMaps

How: Though I used to use apps like Pocket Earth or Ullman, I’m now almost exclusively a huge fan of Google’s MyMaps – it amazes me that this kind of tool is available for free! The interface and customisation options are very intuitive and Google frequently roles out updates and improvements.

I use the desktop version to quickly create and customise the maps which can then be easily accessed and made available offline on my phone via the Google Maps app when I’m on the road.

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7. Draft an itinerary

Why: Picking a rough order for my route has important implications like entry / exit points and can highlight early logistical nightmares (like crossing large bodies of water and mountain ranges). It’s also a requirement for some of those more tricky visas.

What: As simple as a few bullets to roughly shape out my journey, possibly with some initial guesses on how long I might spend in or travelling between each location.

How: My Google MyMap + a pen and paper / Google Docs (if collaborating) / favourite text editor.

At this stage I’ll also go back over any third party travel itineraries I’ve downloaded (like Audley Travel) to check if I’ve missed anything major. I also find it a great time to once again revisit my Why and Success Statements to make sure I haven’t strayed too far from the original purpose of my trip (or to update it)!

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8. Firm up itinerary

Why: Because a quick, early reality check can help save a lot of hassle, expense and disappointment down the line. I’ve found this doubly true when distances are large or travelling during busy seasons (e.g., music/cultural/religious festivals or seasonal events like seeing the Cherry Blossoms in Japan) when tickets, accommodation or travel options might be tight.

What: I usually sense check two things at this point:

  1. Travel times – this where spotting things like the option to take 3 busses over 24h vs. one 2h long flight can reshape my draft itinerary
  2. Booking requirements (tickets, travel and accommodation) – the need to book things in advance varies hugely depending on where and when I’m travelling

I try to leave things as open as possible so if I can I generally won’t book anything except flights much more than a few days in advance.


I’ll often use the resources below to make any major adjustments to my itinerary. I’m a heavy calendar user so at this point I’ll put where I might be each night and any travel bookings I’ve made into my calendar so that it drops into my productivity system and gives me an overview of how it fits into my wider travel plans.

Air Travel: I use SkyScanner‘s calendar functions to spot any savings by shifting my entry/exit dates. Other options include Kyak and Expedia.

Land Travel: GoogleMaps for a rough estimate. Then Lonely Planet, Wikitravel/voyage and lastly Google to hunt down any local travel resources like train and bus time tables.

Accommodation: My reading and travel guides have usually given me a pretty good idea of how far in advance I’ll need to be booking. Couch Surfing, Hostel World, AirBnB and are all great resources to double check depending on budget, location and availability.

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10. Look back on the trip

Why: Aside from the fact that active recall is a critical step in learning effectively, reflecting on the lessons we’ve learned and sharing impressions or war stories from travel is one of its greatest joys.

Taking the time to look back on all or even part of a trip is perhaps one of the most important and yet most overlooked steps in travelling. I’ve found time and again, if I take the time to do a good look back within a week or two of finishing a trip (which I don’t do nearly as often as I should), that the amount that I learn and remember from the trip increases hugely.

What: I tend to use the following six questions as thought starters for my look backs but whatever works for you is the thing that’s best:

☐ What did I do? What didn’t I do?
☐ What did I learn? What was surprising?
☐ What went well? What would I do differently?

How: Wether it’s regularly during the trip or just once a few days or weeks after your return whatever tool you find easiest is probably the best one.

Pen and paper, a diary or your favourite digital note taking tool are all great options. Writing a blog or sharing email updates with your friends and family whilst you travel is another great way to get some of this stuff out of your head whilst it’s fresh.

Not much of a writer? Make time to share impressions and war stories with your travel buddies or even just people you meet who have travelled to the same places over a drink or some food!

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