I often get asked how I plan my trips. That’s when I take a deep breath and think about how I actually do it. It’s actually a good question because I know that trip planning is no easy task. There’s quite a lot involved and it’s different for every single trip but if I think about it, there are a bunch standard things I usually end up doing that makes my life easier.
So this is my art to planning a trip. Big or small, follow these steps when you decide to plan a vacation. Now there’s a reason it’s an art. It’s less science and more of feeling and luck. I also didn’t say it was easy. It can be a pain in the ass but can be really fun as well. It kind of depends on who you are.
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Figuring Out Where To Go And When
I think the easy part is figuring out where you want to go because we all have that “bucket list” that we keep in our heads. What’s hard is deciding where to go especially when there are constraints to work with. There’s a budget to keep to, vacation time that needs to be balanced for the year, others to consider, and your overall mood.
Great, so you have all that to work with, how do you narrow things down?
I think one of the easiest ways to get started on deciding on your next vacation destination is to look for flight deals. As much as wanderlust is strong in all of us, money still talks at the end of the day. If you can score a killer deal to Japan even though you’d love to go to Argentina, you’d likely choose Japan if the money you save on flights can pretty much cover all your accommodation expenses. So with that, make sure you stay up to date with flight deals (*nudge nudge* my flight deal mailing list) or get really creative when using Skyscanner’s “Everywhere” option or something like Google Flights.
Travelling with others is very rewarding but so is solo travel too. This and being able to take vacation days is going to help you figure out when you want to go. Having a limited number of weeks or months to bound your search can make things a ton easier.
Oh and think about “when is the best time of the year to go.” This could be about high season vs low season or maybe there’s a special event or festival you want to go to.
It can also help to know what kind of trip you feel like doing. Are you yearning for a bit of adventure or
Last thing I’ll say here is that you want to think WAY ahead. Last minute travel could come with surprise deals but I’ve always found that this leads to procrastination and the vacation doesn’t happen because something else comes up.
Find Your Inspiration
Now this particular step doesn’t have to follow the previous but this is the part where you go through your go-to spots to research your trips. Everyone has their own style whether it’s books, magazines, blogs, social media, and friends & family.
There really isn’t a right approach to this but here’s my approach for how I eventually assemble an itinerary.
Ask Friends and Family
Know someone that’s been recently or is a pseudo-expert? That’s probably your best source of information. Cut the BS and get straight to what is really worth doing and going to.
If you’re lucky, they might even have a sweet itinerary to piggy-back off of (i.e. if you asked me). Friends’ll actually spend the time to write you an email with their lost of their top choices for where to go, places to eat, where to avoid etc.
The ways I’ve done this is in person, through a chat app like Whatsapp, or posting something on social media (i.e. Facebook or Twitter).
The information is honest and if your travel styles are similar, it can cut down on trip planning stress ten-fold.
Google “XYZ # Days Itinerary”
You’ll be surprised to hear that I’m a lazy person. I don’t always want to sift through a lot of content to get the information I want. If I’m planning a trip, I want to hit up a few websites to get ideas and then start assembling it all. That’s why my personal tendency is to look for blogs that lay out their itinerary.
For instance, when I planned my trip to Taiwan, I stumbled upon this 10 day itinerary, 8 day itinerary, and 2 week itinerary as examples. Each one of them was very different but where it helped me was it gave me a sense of places to go, spacing of events, logistics, and activities to look into.
What I’m looking for are essentially trends for what’s popular, and hidden gems if something unique.
Bookmark them or add them to your Google Sheet for reference later.
The Usual Suspects
This is more of the same as the above but beyond the blogs, there’s still value in going the popular websites that we all know about – TripAdvisor, Lonely Planet Thorntree, Fodors, Frommers, and whichever other big publication you follow.
Whether listicles, articles, recommended itineraries, or reviews float your boat, I always take a quick browse through to see if there’s anything worthwhile to pick.
For TripAdvisor and Lonely Planet Thorntree specifically, these are the forums that I use. Using the the search tool, I look for the destination in question and will often tack on “itinerary” to see what I get.
Oh and remember those things that have a lot of paper and words on them called books? YES! Guide books are still out there so whether you get them from the library (when was the last time you were there?) or you pick them up on Amazon, there’s still a lot of good information in them and they’re updated regularly.
Building Your Itinerary
Make Notes As You Go Along
As you’re doing your inspiration gathering, the worst that can happen to you is when you go “oh wait, I remember reading about this cool place somewhere but where did I see that again?” Oh I’ve made that mistake too many times.
To prevent unwanted brain aneurysms, I’d recommend keeping track of the websites that you’ve been to or copy and pasting the text into a document. Tab city can only last so long and if your browser crashes and god forbid you can’t recover it, it’s much safer to have it on Google Doc or Word Doc somewhere.
I hear the moans and groans already! I recognize that this isn’t for everyone but being the engineer that I am and a lover of cells and pivot tables, I’ve always found that the best way to plan a trip is through a spreadsheet.
Over the past decade or so, I’ve experimented with a lot of different formats and I feel that I’ve figured out the best way to trip plan that’s not overwhelming and easy to read.
- Calendar view – The problem I had with Word files was that it would often span pages and pages and it would hard to see the big picture of what the trip looked like and identify simple things like what day of the week a particular day is.
- Tracking costs – Not a favourite for a lot of people and I know why – it sucks to keep track of your expenses in that it’s a lot of work and sometimes you just don’t want to know. I’ve added a tab to track this stuff and also help with currency conversion and reporting. Nothing super fancy and sure you could use an app but it helps to have this tab.
- Accessible from anywhere – You want to be able to plan on your desktop because that’s the easiest way to do it but you also want to be able to access it from your phone and when you’re on the go with no data. Google Sheets’ offline feature solves that with ease.
- Shareable – Okay I feel like I’m becoming a salesperson for Google Docs here but it’s important that you can share with your travel buddies and Google Sheets does just that.
- Template – The key to making something useful is that it needs to be re-usable and quick to fire up. I like the fact that I have a template now and I just make a copy every time I start planning for a new trip.
This is definitely not the be all and end all of trip planning techniques as I know everyone’s different but it’s worked for me and has helped me streamline everything to a certain degree. The bonus is that I can share these with all you lovely people after I’m done!
Map It Out
This is kind of new to me as I typically do this on the fly or put it all together as part of my post-trip blogging but I’m thinking there’s a good value in seeing your trip map ahead of time.
🇯🇵 The inspiration for this idea came from Mark Wiens here but what I’ve done for Japan but I’ve found it very helpful to see where all these restaurants are located to be able to figure out what neighbourhoods we should do and how we can break out our itinerary.
The nice thing about this is that you can view it on the Google Maps app as long as you’ve either saved the offline map of the area or if you have access to data. There could be user experience improvements here but it’s cross-device compatible and offline capable which is nice.
Piecing The Puzzle Together
I think one of the reasons that we all love (or hate) to plan trips is because it really is like a puzzle. You have all of these odd-sized pieces from this giant bucket and you have to somehow combine them all together. Some pieces don’t work with others and there’s always more pieces than you need. Oh and there’s also no right answer. The fun of trip planning is the challenge of it all.
It kind of depends on the trip but all I do is essentially start filling things into the calendar and move things around as I try to make sense of it all.
When it comes to booking, there’s generally an order of operations that I follow.
- Flights – These are the anchor to the trip so this is usually the first thing I do. If you want to do a flexible search, Skyscanner’s Everywhere feature is pretty handy.
- Accommodations – This isn’t always easy as you kind of need to know your day splits in each spot you’re going to but you usually want to get your nights stay booked (I recommend Booking.com). You have to be careful here though because if there’s an activity that you really want to do and it’s only available on a certain day, you may have to re-adjust by moving things around or extend/reduce. In the case of our honeymoon, I had to completely re-order the trip when I found out that Elephant Plains Game Lodge could only be done at the beginning of the trip instead of after Kruger National Park which was the original idea.
- Car rentals/other ground transportation – As you figure out where you’re going to need to be each day, you’ll want to start figuring out the transportation logistics. I usually book car rental pretty early on because again it’s no commitment and I can lock a car in before it sells out and usually at a better rate. Make sure you check out my ultimate list of car rental coupon codes.
- Excursions and activities – Anything that requires booking comes next and could be in conjunction with accommodations. Just remember that sometimes winging activities may not work out for you so you need to do your research to see what are absolute must-books. Make sure to check out GetYourGuide because I have a 20% off discount code (contact me).
- Restaurant reservations – If this is a super hard-to-get reservation, your whole trip may revolve around this or if there’s just a place you have in mind and you really want to go, it’s better to make a reservation. You usually don’t have to put a deposit or leave a credit card down so these are always easy to change afterwards.
As your spreadsheet is starting to fill up and things are starting to make sense, the rest is all about the fine-tuned details.
- What’s the weather like?
- What do I need to pack?
- Do I need to exchange money?
- Should I buy travel insurance? – The answer is yes and you should check out World Nomads to find the cheapest rates.
- Did you offline download your maps or apps?
I’m probably forgetting a few things but you catch my drift right?
So once is all said and done, you end up with a full Tokyo Food Guide on where and what to eat that is the culmination of all that research and planning. Of course as a blogger, I have to focus on a lot of details in making sure it’s a useful guide but it shows you everything that I planned for and also things I had to learn along the way
That’s a look inside my art of trip planning. It may seem too hardcore…or maybe not hardcore enough but to each’s own. My hope for this article is to give you new perspective from someone else that does a lot of trip planning.
Stock images via Burst
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Travel Resources For Your Next Trip
If you’re in the process of planning your trip and putting together your itinerary, these are genuinely the best resources that the Going Awesome Places team stands by 100%.
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Hotels: Our go-to is Booking.com because they have the best inventory of properties including hotels and B&Bs. The exception is Asia where Agoda always has the best prices. TripAdvisor is also useful for reviews and bookings.
Vacation Rentals: Airbnb is the market leader but you’d be surprised how you can find cheaper deals on the lesser-known VRBO.
Travel Insurance: Learn how to buy the best travel insurance for you. This isn’t something you want to travel without.
- Insured Nomads – Popular insurance provider for frequent travelers and comes with great coverage and special perks.
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- SafetyWing – A perfect fit for long-term nomads.
- Medjet – Global air medical transportation.
- InsureMyTrip – Best for seniors, families, and those with pre-existing conditions.
If you need more help planning your trip, make sure to check out our Travel Toolbox where we highlight all of the gear, resources, and tools we use when traveling.