How To Avoid Over-Planning Your Travels
Last Updated: September 30, 2025
OVER-PLANNING YOUR TRAVELS LIMITS YOU. HERE'S WHY.
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"...what have I done?"
At some point, this question hits everyone who leaves it all behind, and goes backpacking.
You're leaving your comfort zone, moving beyond your support network, stepping into the unknown...
And that shit is scary!
This isn't a holiday. You're dealing with a ton of uncertainty, and the way humans deal with that is to plan. The more uncertainty; the more planning.
We get you. We've done it.
This is particularly true for new travellers - it's your first soirée, and you have NO idea what to expect. So you arm yourself with everything you think you need to know.
Some planning is helpful. However, over-planning your travels can, counter-intuitively, be unhelpful.
So... how much is too much?
Planning vs. Over-Planning Your Travels
Some stuff needs planning. Fact. There's no way around it.
At a minimum, you need to plan where you're going, and how you're getting there. The obvious example is booking a flight.
Once you've got those bare bones down, you can either continue planning, or head off to the pub for a celebratory pint.
The Under-Planners
You decided to go to the pub. In a few days, you'll pitch up at the airport with some sunglasses and flip flops stuffed in a bag, and you're gonna wing it.
It's gonna be one hell of an adventure! But you will miss out on some epic experiences.
Let's say you touch down in Peru, and, a few days in, you've just had the bright idea to hike the Inca Trail to Machu Picchu.
Well... bad luck. You can't. Your flip flops can't hack it, and you need a permit. And those sell out months in advance.
Which a quick Google would have told you.
You'll find several other epic adventures, don't worry! But you'll miss the main event.
Your stories will all contain the phrase, "Well, you're not gonna believe it, but...".
The Over-Planners
You sack off the pub, and start planning your trip of a lifetime. There's gon'st to be an itinerary!
You're gonna pour endless hours into assembling your own bespoke adventure. You'll know every bus number, entry fee and well-reviewed restaurant. Knowing all this information helps settle that feeling of uncertainty. You know what to expect now!
These notes start to get out of hand, and so you organise them. You end up with a colour-coded, to-the-minute itinerary. With cascading tabs. And a contents page.
Because who doesn't love some wild, rigidly-scheduled fun?!
... And what's wrong with that?!
On paper... not much!
You know everything you want to do, you're going to have a roof over your head, and you've booked those all-important Trail permits. All sorted... right?
Well, yeah.
Until you get there, and realise you've cocked up a bit.
Here's what you'll find:
Problem One: You have no freedom
As it turns out, travel isn't so much about the 'travelling around' bit. It's actually about the people you meet, and the freedom you have to explore.
Let's put it this way...
Say you're chilling on the east coast of Australia, and you've stopped in Airlie Beach for a couple of nights. You're due to head down to Brisbane in two days, and you've got your Greyhound bus and Brissy hostel booked and waiting for you. Tomorrow, you're gonna pick up a day tour to the Whitsunday Islands.
That night, you get an invite to the pub. Which you take.
You end up hitting it off with a group of backpackers, and, before you know it, you're doing a Coyote Ugly off the end of the bar, hitting back shots and making friends for life. And then they have a brainwave.
"Oi, wanna come to the Whitsundays tomorrow?"
Turns out, they've chartered a catamaran for five nights, and they're island hopping with a boatload of booze. And... there's a spare bed for you! You're taking it, aren't you?
Wrong.
Over-planning your travels has shot you in the foot.
You're now a hundred dollars or so committed to your itinerary, and saying 'yes' would throw the whole schedule.
So... what do you do?
Ask yourself this: what's gonna be a better experience? A routine day tour with a bunch of families you don't know, or a five-night floating extravaganza of snorkelling, music, barbecue, booze, and mates, around some of the prettiest islands on the planet?
Both will be fun.
But one is more fun.
Over-planning your travels has meant you've missed out.
Problem Two: The world doesn't care about your schedule
If you're from the West, you're probably used to things happening at certain times. Your bus arrives at about 2:54, you finish work at 5, the match kicks off at 3...
Yeah, not so much in the rest of the world.
Let's take Bali. That bus you had planned to get you from the airport to Canggu might arrive... or it might not. It could be an hour late, it could be full, or it could have broken down two days ago.
On top of that, your schedule (powered by Google Maps) says that route should take 44 minutes. Which means the one thing you can guarantee is it won't take 44 minutes. South Bali's roads are just too unpredictable - one crash 5 miles west can cause hours of delays. Greg spent over two-and-a-half hours on that journey.
There simply isn't the infrastructure in most of the world to keep a tight schedule.
Problem Three: Following a strict itinerary is knackering
Everyone overestimates how much they can fit in a day.
The classic example is exploring cities. You've decided to visit the watery delights of Venice, because you love pizza and Venice is stunning.
You've scheduled a generous two hours after lunch to have a look around St Mark's Museum - the largest in town - which leaves time to check out the Doge's Palace before it closes at 6. A solid plan, right?
It is, until you step inside St Marks and see just how massive it all is. Two hours in, you'll be about halfway.
So... do you rush to try and see it all; skip half the museum to make it to the Doge's Palace; or miss the Palace entirely?
Even having to worry about that decision is stressful. Knowing that there's no flexibility to reschedule tomorrow adds pressure, and you've been on the go since you went to watch the sunrise over the canals. Oh, and you have a dinner reservation at 8.
Suddenly, this isn't all that fun, is it? It's just work.
You've been over-planning your travels again, haven't you?
So, Here's How To Avoid Over-planning Your Travels
The flaws in under-planning are pretty obvious. But over-planning your travels can be just as detrimental.
So... what should you do?
What's the 'right' amount of planning?
When it's freedom and flexibility versus planning and itineraries, where's the sweet spot?
The Solution To Over-Planning Your Travels? Only Fill In The Broad Strokes
We suggest only getting the broad strokes of your trip scheduled in. Sort the big bits, and the little bits will fall into place around them.
Our trips look something like this:
- We come up with where we want to go.
- We do a light bit of research to see what the 'main events' are. Do we need to go at a certain time, or book something ahead? Think the Inca Trail permits. You don't want to pitch up in India wanting to experience the Holi festival, and find it's nine months away.
- Then we book flights - ideally one-way.
- Finally, we book the first few night's accommodation. This lets us get a feel for the hostel and the area. If we like it, we can extend when we're there. If we don't, we move on. Simple.
The rest is pretty freeform. We research on the fly, tapping into local knowledge, tips from fellow backpackers, and generally going for whatever looks good!
The key thing is this: you'll find internet everywhere these days. Armed with the right apps, you can book your next day's accommodation, tickets and transport on the fly.
Which is what we do.
This way, you can make sure you're there for the big events, but if you meet some mates and decide to get a camper and drive 3000 miles west... you can do that too!
The truth is, that feeling never goes
Everyone still gets that "What have I done?" moment, whether it's the first time or the thirtieth.
Whether you've arrived at the airport with a binder of notes or just a hangover and a passport, you're still gonna have that moment. It gets all of us.
And over-planning your travels isn't gonna fix that. Hit out the basics, sure, but leave some wiggle room for the spontaneous shit that makes a good trip exceptional.
Travelling isn't about the schedules. It's about the adventures you have. You know how they say, "The best nights out are unplanned"? Well, that applies to backpacking, too.
So why not give yourself time to have some adventures?