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Our 25-Step Trip Planning Checklist

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While this is the first time we’ve attempted to formalize our trip planning checklist, we’ve been roughly following this pattern for at least a decade now. So, starting with our mental processes for choosing destinations right on through to choosing the right number and colours of underwear, we have put together a trip planning checklist that will hopefully help your trip go as smoothly as possible, meaning less time spent dealing with problems and more time taking ill-advised selfies next to every naked statue.

While it may seem like we travel all the time, we actually make a concerted effort to split up our trips and have some time at home every now and then. And one of the main reasons is so we can regroup and work our way through our trip planning checklist before hitting the road again.

Woman working on trip planning at a table on the beach in Thailand

It’s always important to make it back home to see family and friends, enjoy our short but beautiful Saskatchewan summers, reset, restock and repack before the next adventure. Getting off the plane to prairie winter weather in December? Well, that part we could probably do without but, hey, Christmas is Christmas, and it’s much more fun to be home for it.

The other reason it is nice to have a break in between journeys is because these trips don’t just happen on their own. They require trip planning and travel preparation in order to make the most of our time and money. Sure, there are some who prefer to “wing it”, and that can be an admirable idea.

However, in our experience, those people usually just end up missing out on a lot of the best stuff and spending far too much of their travel time figuring out logistics, seeking recommendations, overpaying for the only hotel with rooms available and waiting at all the wrong bus stops.

Woman in mouth of cave overlooking a blue water bay
Cyprus

Routinely Nomadic Trip Planning Checklist

1. Decide on Destinations and Itinerary

This is probably the hardest part and the most fun all at the same time. I don’t know if you’ve noticed but the world is very large. And there are LOTS of things to see. Like, dozens, even. So deciding where to go next (or the time after that, or the time after that, depending on how far in advance we’re planning) can be very challenging.

Plus, there are two of us, making it that much trickier. And, as some of you may have noticed, every now and then Laynni and I have, um, differing opinions. So there is a fair bit of compromise involved as well.

For those starting from scratch, here are some very basic questions that need to be answered before you move on to the main details:

How long will your trip be?

What time of year do you want to go?

What is your budget?

Do you want longer stays in one or two places or to see multiple places for a short time each?

Do you prefer to travel independently or go with a tour to have all the details handled for you?

Personally, we stay home for most of the summer, travel for a few months in the fall, come home for Christmas, then hit the road again for 3-4 months starting in January, with that stretch almost always including 2-3 months ensconced in our usual apartment at Lake Atitlan (Guatemala).

Woman walking through garden with lake and volcanoes in the background
Lake Atitlan

We only take tours for very specific experiences and usually not for very long (we find that both guides and travelling with strangers become exhausting rather quickly), so most of the time we are travelling independently. And, even though we keep daydreaming of doing a “seven 1-month stays winter”, somehow we always ending up chopping it up into smaller chunks here and there once we start researching more details on each place.

So, once those questions are roughly answered, our overall trip planning process goes a little something like this:

  • Determine the trip time-frame
  • Make a list of priority destinations and activities
  • Rule out any that won’t work for the season we’re considering
  • Estimate the amount of time and specific dates that work best for each
  • Begin building potential itineraries, starting with the top priority and working our way down
  • Brainstorm additional destinations reasonably reachable from the priorities (I find Google Explore is a great way to find good connections between destinations)
  • Offer Laynni some time in one of her favourite spots (usually the Greek Islands) to help convince her to do whatever big hike I’m trying to talk her into
  • Fill in gaps in the timeline with places that can be used to connect the top spots

And, just like that, you’ve got a trip planned. Well, more “planned” than PLANNED, if you know what I mean. And if you don’t, well, we’re getting to that part.

2. Research Transportation

Start with the main flights to and from the regions you’ve chosen – in our case those tend to be one-way flights because we always seem to finish as far as humanly possible from where we start. But more reasonable people may be able to stick with a (gasp!) return flight, especially if you’re talking about a shorter trip.

For checking out flights we find that SkyScanner is usually the best. Google Flights is the fastest  but often once you choose a flight it either isn’t actually available or is different than they showed. Which is obviously pretty annoying.

Either way, it’s also important to look into the smaller connections as well, whether those are more flights or trains, buses or ferries. Every now and then we are surprised to find two places that you would think connect easily are, for some reason, practically impossible to travel between. Or at least impossible without suffering through multiple train connections in every town in Italy, or an extra 15 hours on ferries taking you back through Athens (overnight! yikes!) or flying all the back to Gatwick before heading in the right direction (EasyJet, I’m looking at you).

The point is, don’t just assume you can get from one place to another easily because it seems logical. If there is one universal travel truth we have learned, it is that logic is pretty scarce. Well, that, and that Laynni gets really irritated when I use the phrase “I’m sure there’s a <insert randomly hopeful transportation option>” even when the internet tells us otherwise.

Woman hanging on outside of a train
Sri Lanka

Trainline is great option for, well, trains, obviously. We like BusBud or FlixBus for buses. FerryScanner has one of the best ferry networks in the world, is the most user-friendly site we’ve come across and is the site we use to book all our own ferry trips.

3. Calculate a Budget

This can be tough since spending varies so widely from person to person. However, we can usually get a pretty good idea of how expensive a place is by the price of the hotels. Then you can look at some restaurants and reviews to come up with an idea on food spending. We often plan to eat out half the time and self-cater the other half.

Self-catering can mean anything from full apartment meals to makeshift convenience store breakfasts and street food lunches. VERY roughly, these meals tend to cost from 1/4 to 1/3 of a restaurant meal.

You can look into hotels and transportation to get an idea about those numbers, then a rough estimate on food, plus any other tours/transport/entrance fees you know of. Finally, we always add in a generous number per day for incidentals that will change by country. For example, we might expect to spend an unplanned $US10/day in Guatemala but more like €20/day in Europe.

Once you have a general idea of what the entire trip will cost, round it up (considerably, if possible) and make sure you have enough cash available between bank accounts and credit cards.

4. Book the Important Stuff

By that, I mean trekking huts, diving liveaboards, destination hotels or specialty tours. Anything that is a major priority or focus of the trip that could potentially get booked up. Our trip planning often starts with some type of long-distance trek, many of which have one or two specific stops along the way that are particularly popular and can be fully booked months in advance. So we usually start there and work our way out.

Couple scuba diving
Maldives

5. Book Your Main Transportation

Now that you know you’ve got a bed at Rifugio Bonatti on the Tour du Mont Blanc or a car reserved for Monkey Kart in Tokyo, it is time to commit. Very generally, we find the prices on international flights tend to be best 3-4 months before departure. However, we’ve seen many, many exceptions to that rule and we always start looking as soon as we start tossing ideas around.

Based mainly on experience, we now have a pretty good idea of what constitutes a “good price” for any given flight, although that is clearly very subjective and influenced by what we’ve paid for similar journeys in the past.

Once again, SkyScanner is usually the best choice. You can also save your searches to be notified about price changes.

6. Research Destination Details

So, you now have flights and a rough itinerary. Now it’s time to start digging a little deeper to figure out specifically what you want to see and do and how much time you need in each spot. For example, trip planning for our 2023 fall travels started with deciding on 5 destinations and rough timelines for each – the Catalonia region of Spain (3 weeks), Greek Islands (2 weeks), Istanbul (1 week), Japan (5 weeks) and Vietnam (3 weeks).

Woman on viewpoint overlooking cliffs and an island
Zakynthos – Greece

Then we needed to get more specific:

How many and which Spanish towns to visit after we’re done punishing our bodies in the Pyrenees?

How many and which Greek Islands this time?

How many days do we need around Mount Fuji to give ourselves a good chance of a clear day but not so much that we get bored?

Limestone karsts or rice paddies in Vietnam? Both, obviously, but how to split the time?

7. Start Booking Hotels

This is the part some people might disagree with. We tend to book our hotels quite early. Yes, it is almost always possible to find rooms closer to the date of your stay but, in our experience, thanks to the ease of online booking and prevalence of free cancellation, most of the hotels available at the last minute fall into one of two categories:

1. Expensive

2. Shitty

Neither of which are ideal. We find the vast majority of our hotels on Booking.com, with a growing list of apartments and long-term rentals on there as well. Between the frequent stay discounts, thousands of reviews and free cancellation it is very rare for us to have a bad hotel experience these days. For long-term rentals, we sometimes use AirBnB but the fees are higher and the cancellation policies are usually stricter.

Terraced green rice fields
Bali

As for choosing specific hotels, we would recommend liberal use of the filters – narrow it down to your absolute dream scenario (9+ rating, separate bedroom, washing machine, etc) and only expand your search if nothing fits those criteria. I would also recommend having Laynni do all the work of browsing through dozens of hotels, narrowing it down to a couple of choices for you to choose from, even though she has already subconsciously picked one, making your opinion essentially moot. I find this method works best for us.

Another little trick is to book hotels with free cancellation, then check back before it runs out to see if prices have gone down or another rockstar hotel has come into your price range.

8. Plan Local Transportation

This means reserving car rentals, buying bus tickets, researching rail passes, etc. Don’t wait until you’re hauling your bag off the airport carousel before trying to figure out how to get into the city or find your hotel. In case you hadn’t heard, there is a fair bit of info on the internet these days. Make it useful.

When it comes to car rental, Discover Cars doesn’t cover quite as many places as some of the other sites but is still the first place we look since they’ve provided some of the cheapest deals we’ve found anywhere in the world.

Couple selfie on a scooter on a dirt road
Koh Yao Noi – Thailand

9. Destination Outlines

Now, for blog reasons, we do this much more thoroughly than most people would ever need to. I like to research each destination that I expect to write about and make an outline to make sure we don’t miss any of the important stuff.

But even though you’re probably not planning to jot down 4,000 words on, say, some unpronounceable canyon in Iceland, for trip planning purposes it is still important to know what you want to see and do in each place.

Man standing on a cliff looking down at Mulagljufur Canyon

We recommend a basic Google search, then wading through the sponsored ads and TripAdvisor tripe until you find some firsthand blogs that breakdown all the highlights and top experiences. Or if you prefer video, TikTok and YouTube are essential resources.

This research will help you narrow down your priorities and focus your time on important things (i.e. a classic medieval bridge), rather than wasting your time on unnecessary add-ons (i.e. the pigeon-shit-covered statue of some random colonial bully).

10. Customize Google Maps

Within Google Maps you can save places using different icons – we use the green flags for places we want to see (mainly because Google has titled it “Want to See”), and use the gold stars for many other things, such as hotels we’ve booked, the car rental office, the nearest grocery stores, the best places to pick up more band-aids, etc.

If you happen to be visiting somewhere we’ve been and written about, there will probably already be a customized Google Map in our post that can be saved to your phone and edited as needed, saving you some time.

11. Download Offline Maps

Regardless of how much work you put into customizing your maps (on a scale of 1-10, with 1 being “yawn” and 10 being “I went down the rabbit hole and haven’t slept since Monday”), you should always download maps for offline use.

Even if you expect to have data on your phone during your trip it is wise to save maps ahead to allow you to navigate with or without a signal or data. On Google Maps, just click on the menu symbol, choose Offline Maps, then choose the area you want to download. Most custom map downloads last for at least a month.

Man resting on a rock in the Nepalese mountains
Nepal

12. Download and update apps

Think about all the apps you expect to use (Google Maps, Accuweather, Chrome, AirBnB, Booking, banking apps, etc.) and make sure they are up to date while you still have a reliable internet connection. Also, make sure you have the latest version from any airlines you’ll be using as you often need the app to access the online entertainment and other features.

And always – always! – keep your Pokemon app updated. They take that shit serious. You can’t even open it up unless it’s right up to date. Alarming, to say the least.

13. Plan Your Local Currency

Yes, in many places around the world you can now pay mostly with credit card (Visa works best), and if you have a Plus (the better choice) or Cirrus bank card you should be able to get money from ATMs all over the world. But they don’t always work quite the way you’d like, especially in developing countries. Always try to have your money accessible through 2-3 (or more) different cards since you never know when a foreign ATM might randomly reject one of them.

And it is also comforting to have a little cash in your pocket when you arrive to at least get you to your first stop, plus a bit to carry around when you’re in more rural areas. Although it can be fun to try tipping the local guide taking you through the Vietnamese rice fields with Apple Pay, just to see the look on his face.

Woman looking down at beaches and mountains of Koh Phi Phi
Koh Phi Phi – Thailand

If you travel a lot or get paid in a foreign currency, you should consider setting up a Wise international currency bank account. Both of which apply to us, which is why setting up a Wise account is probably the best financial decision we’ve made in the last few years.

We can send and receive money in half a dozen different currencies, convert to dozens more with no exchange premium and pay or withdraw local currencies. It’s been a game changer. Not everyone uses currency exchange as much as we do but still, I figure we saved close to $3,000 in the first year alone.

14. Make a Packing List

We have a very general long-term travel packing list we start with, then customize it to fit the specific trip we’re taking. One of the big decisions you have to make is whether you’ll be checking a bag or sticking to carry-on only.

If you’re going to check a bag, be sure to put all liquids into the checked luggage and buy an AirTag so you’ll always be able to track your stuff even on the bizarre off-chance that the airline DOESN’T actually treat your bag like it is full of delicate internal organs meant to save their grandma.

Then, anything important that you don’t want to lose, isn’t easily replaced or that you don’t want to be without even for a day or two goes on the plane with you (i.e. laptop, most comfortable underwear, anti-psychotic medication).

You will also need to decide on the type of luggage you’re taking. We still go strictly backpack because we almost always have some hiking on the agenda and as good as those little rollie suitcases have gotten, they still don’t deal well with rocky mountain trails.

Man hiking in the Dolomites
Alta Via 1

Our main debate is over our personal item, so to speak. Usually we go with a fairly solid little daypack to carry our laptops, then a reusable grocery bag for extra clothes and pillows and such on the plane. Don’t judge us (the guy next to me staring at my stained pink Vita bag has already done that enough).

This isn’t a definitive list, by any means, but as long as you remember the following essentials you should be able to salvage pretty much any trip:

Passport

Credit Card

Phone

A merino wool shirt

5 lip balms

15. Buy Travel Insurance

Unless you are a daredevil lunatic who gets tingly feelings in weird places at the thought of gambling your financial future on the whims of some random foreign hospital, you should always make sure you have travel insurance. Like any insurance, you hope to never use it, which we never have, ultimately making it one of the most annoying things you can spend money on. But still, the alternative just isn’t worth it.

Tiger Shark up close
Tiger Shark

On short trips, the difference in price between companies will be minimal so you can probably just go through your bank, travel agent or whatever website you book your flights through. For longer trips, though, there are fewer choices and bigger differences.

World Nomads is one of the best long-term global insurance options for most nationalities. It is especially good for people who travel a lot with specific plans for both regular travellers and digital nomads.

Canadians looking for single trip coverage could also get a quote from Destination Travel Group. Their coverage isn’t as broad as World Nomads but they tend to be cheaper.

16. Buy an eSIM

Everywhere we go these days we buy a local SIM card so we can use our phone normally. Unlike the extortionate prices in Canada, this is usually surprisingly affordable. We always want to have data whenever possible, plus sometimes it can be very handy to be able to call your AirBnB, the airline or just that number you found in the bathroom stall in the bus station (assuming you are, in fact, looking for a good time).

Of course, on very short trips it might be just as easy to activate your international roaming and pay the fees, but for anything trip longer than 2 weeks we would recommend getting either a local SIM or one of the relatively new eSIMs.

In some places, local SIM cards are still the best choice (i.e. Guatemala, Mexico) so you’ll need to wait until arrival to pick one up. But for almost everywhere else in the world, an eSIM is far more convenient.

After extensive research (talk about a serious rabbit hole), I have decided that KeepGo eSIMs have the best coverage and prices for most of our trips. They are extremely easy to install – you receive a QR code by email that you scan, then it will walk you through the setup. It’s also nice that it will be ready to go immediately once your arrive.

Man looking down at narrow beach and island
Balos Beach – Crete

If you have a relatively new smartphone (iPhone XR or newer, Samsung S20 or newer) it will have the capacity to hold both a physical SIM card and an eSIM. That way you can keep your main SIM card in the phone and purchase an eSIM that lasts forever along with a travel package that covers your destinations. We recently paid about €15 for 10GB covering all of Europe (plus more) with no expiration date. Highly recommended.

17. Go Trip Shopping

If you did a thorough job on your packing list, by now you should have a pretty good idea of what you still need to buy for your trip. Or maybe you don’t need a trip planning checklist to remind you that your best hiking shirt has holes in the armpit or that your little pack towel has developed a permanent mossy odour.

18. Learn the Language

Ok, maybe not the entire language. Unless you’re going to Indonesia – that one’s basically a flash card exercise. But most other languages take years of study, focus and practice just to reach the elusive “hey, that sort of made sense!” status (and a perfect description of my Spanish, incidentally).

As native English speakers, we feel incredibly lucky that English has become the default travel language in most places. These days, even where not much English is spoken, chances are there will still be quite a few people in the tourism sector that know enough to get by. Hotel and restaurant staff, guides and tour operators, helpful ATM conmen, just to name a few.

Nonetheless, learning even a little bit of the local language can go a long way and really change the vibe of an interaction. Knowing how to say “it is nice to meet you” and “can I see a menu, please” in Turkish may not completely smooth things over with the cop who arrested you for trafficking meth, but it certainly can’t hurt.

Colourful streets in the Jewish quarter of Istanbul
Istanbul

I usually make a spreadsheet with translations for a lot of the most important words and phrases in each language we’re going to encounter. The list can be anywhere from 10 to 100 words depending on how long we expect to be there and how much English is spoken. But here are the ones I consider particularly useful that should cover most common situations:

Hello / Goodbye / See you later

Yes / No

Please / Thank you / You’re welcome

How are you? / Fine, thanks / Pleased to meet you

Menu / delicious / bill

Water / tea / beer / Cheers!

Harder / softer / faster / slower

Excuse me / I’m sorry / I don’t understand

19. Start Adjusting to the Time Change

This one only applies if you have a significant east/west trip planned. And it’s debatable how much it even helps. But after years of dealing with time change and jet lag we have concluded that the standard cliché about how long it takes your body to completely adjust – 1 day per hour of time change to completely adjust – is pretty much right on the money.

Woman on a bridge in Venice with a reflection in the water
Venice

But it certainly makes it easier if you get a head start – if you’re heading from North America to Europe, start waking up earlier since pretty soon you’ll be expecting to check out of your hotels when it’s 4 am back home. Or stay up later if you’re heading west so you don’t end up snoring into your bowl of pho because it is once again 4 am at home, but now you’ve been awake for 15 hours already.

20. Start Your Farewell Tour

Once again, the length of trip is pretty key here. If you’re just heading to Iceland for 2 weeks and you start having deep, heart-to-heart visits with all your soccer buddies they might get weirded out and next thing you know you’re out of the starting 11.

But for longer trips like ours, we try to schedule final visits with our closest friends and family members ahead of time instead of waiting until the last two days when we’re trying to pack and plan and move out and inevitably just end up sending apologetic texts with lots of shrugging emojis.

21. Stock Up on Entertainment

Meaning add books to your E-Reader, download Netflix content and make music playlists. To quote a friend who recently learned that we don’t subscribe to any music streaming services and still simply buy albums and make our own playlists – “I don’t even understand what you’re telling me right now, what planet are you from?” So it’s possible that making playlists may not be a critical part of your trip planning process.

However, keep in mind that there are always times while travelling when you won’t have cell service or have service but not enough data to spend any of it streaming the most recent posthumous Linkin Park release. So having some music on your phone can’t hurt. Not to mention some books (on phone or e-reader) and maybe some audiobooks or podcasts.

Likewise, even though we can use most streaming services anywhere in the world as long as we have wifi, our trip planning always includes downloading a stash of Netflix shows and movies for offline use, as well, for those times when bandwidth is at a premium.

22. Backup Phones and Laptops

You never PLAN to drop your phone in the toilet or have your laptop stolen by some enterprising young delinquent. But those things still happen occasionally. And when they do, you’ll be happy you backed everything up before you left.

It is also a good idea to clear your caches and passwords in case the new owner manages to get past your seemingly impenetrable laptop password (presumably your cat’s name followed by a 1).

23. Pack

All the items of a tour du mont blanc packing list spread out on the floor

Some prefer to leave this to the last few hours but I can say, from experience, this is the leading cause of divorce discussions. Much better to get everything washed, sorted, rolled and packed at least a day ahead. If for no other reason than you now have at least 24 hours to decide what to leave behind since there is NO way you’re carrying a bag that size around for the next month.

24. Check-In for Flights

Most airlines allow you to check-in 24 hours before the first leg of your journey. Although definitely figure this out when you book your flight since some airlines allow 48 hours and a few of the budget airlines we use will even let you check-in a month ahead (desperately hoping you’ll mess up somehow and incur some preposterous fees).

25. Ask My Parents for a Ride

They have a lot of time on their hands these days so as long your departure doesn’t overlap with one of the grandkid’s sports, it should be fine. Just know that if you’re leaving before 8 am, mom will probably make dad drive us. Don’t worry, though, she’ll still make a groggy goodbye appearance at the door in her robe.

Downloadable Trip Planning Checklist

Trip Planning Summary

Pool and palm trees at sunset at the Riu Mazatlan

All right, I think you’re ready! This trip planning checklist can’t account for every consideration unique to a specific trip but it should cover most of the important stuff. And, obviously, the order can be tweaked as needed.

The only non-negotiable is to always carry at least $4 worth of Guatemala quetzales. You just never know when you’ll be too drunk to walk home from a tiny Mayan village and, let me tell you, those tuk-tuks do NOT accept Apple Pay.

Other Posts You Might Like:

Travel Tips: 40 Things We’ve Learned

Long-Term Travel Packing List

7 Steps to Save Money and Travel the World

How to Travel on a Budget

Burning Travel Questions

Slow Travel: Settling in for the Long Haul

Day Hike Packing List

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