What 300+ Flights Taught Me How to Plan (Awesome) Trips

One of the worst feelings is when you finally land on a trip you've been planning for months and yet it's not fun and full of regret by the time you head home.

Turns out the problem is almost never the destination or the inevitable curveballs, but rather is almost always an obsession with maximizing a trip all while examining maximization through the wrong lens.

In other words, maximization isn't about the number of things and places you hit up. It's maximizing your desired positive feelings by the time the trip comes to an end. But okay, how do I actually plan a trip? Step one, the big daily do. You see, maybe you've booked a oneweek trip and through your research, seeing travel guides on social media, reading top 10 lists and all of that.

You might have a list of a 100 things that interest you, right?

But you already know there's no way to strike through that checklist. And so the big daily do is taking your honesty with yourself about your true motivators and identifying the most important to spread throughout your trip. In other words, the one thing where if it happens makes that day a success. Could be a particular restaurant, a unique Instagrammable wall, a museum, whatever feels meaningful to you, not impressive to anyone else. And when examining your full checklist against your own true motivators to visit your destination, in my experience, this is shockingly easy.

I mean, the cream rises to the top real fast.

And that decision fatigue from your list of 100 naturally pairs down to each 24 hours big daily do very quickly and easily.

And of course, I'll show you what I mean soon. But once you hammer out your big daily due for each day of your trip, the rest of each day totally open.

I mean, again, I'll show you how I incorporate other items in that initial huge list, but the point is, for me, after sailing on over 350 international flights, I've realized that the less I plan, the more I end up doing.

Each day ends with a very unique feeling, deep fulfillment, as opposed to checklist satisfaction.

However, before showing you the literal planning hack when traveling, there is one checklist that does need to be satisfied, and that's the fact that we simply have to carry more things than we typically do on home turf.

And that's where this segment sponsor, TomTalk, comes in, especially with their Aviator line of slings.

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I rarely actually use my passport and emergency cash, and my hotel key card is only used when I return after a day of exploration.

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But okay, you've got your big daily dues identified, but how do you actually plan?

And then just as importantly, how do you potentially strike through other items on that initial huge list?

Answer, your custom Google map. And you are about to see how incredible this completely free tool is. I mean, my custom map becomes the anchor for the entire trip.

I'm going to go into a bit more detail in about 20 seconds, but you can see I have a dedicated layer for all of my big daily dues, but also can add additional layers for food spots, scenic views, shopping, all with the ability to custom name things with custom notes.

For example, that one cafe that one person on Reddit mentioned. This way, I can see everything not as a checklist, but as a geography. You quickly start realizing, wait, that cafe in my nice to have layer is literally a 2-minute walk from day three's big daily do.

Or that vintage bookstore is one subway stop from the museum from day four's big daily do.

You see, it's less about controlling the date and more about understanding the city.

The custom names, notes, and color codes can all be toggled on and off to simplify your view when it suits you best. And best of all, they're tacked onto the real navigation tool called Google Maps that will guide you to the most efficient route between everything, whether it's walking, public transit, or a cab. This means that when you wake up each day of your trip, instead of rethinking everything, you just glance at the map, head to that day's big daily do. Then once that's done, see what else is nearby, and just explore.

It's structure without a schedule.

So, let's take a look.

There are three days straight in Taipei in my upcoming trip where there are zero meetings booked.

on my custom Google map for those three days. My hot pink layer are my big daily dues. Blue is my accommodation.

Yellow are all the potential meals that my research has recommended.

Green are both interesting sites and landmarks, and gray are potential shopping spots.

But most valuable is a dedicated notes section for each.

For example, I can copy and paste the reservation link for a restaurant in the notes section, so it's fast to find if I do decide to try and reserve a dinner there.

Remember, this lets you orient your entire list geographically instead of drowning in checklist overload.

Before sharing a speedrun of my own research best practices though, I got to say at this point at least a few of you have probably thought to yourself, Maurice, more than 90% of your travel is for business, which means it's solo travel.

What about if we're planning a trip for a group?

Honestly, to me, almost nothing changes.

Every adult involved in a trip should start with the selfishness in step one and continue with the selfishness of their own big daily dues for every day of the trip.

Once that's done, it'll be very easy to coordinate between alone time and squad time.

In my experience, if traveling in a group of adults, the best strategy is to just commit to one shared meal per day or two throughout the trip. Everyone, or rather every adult, can then plan what their selfish, awesome trip would look like.

And hey, if there's crossover, some can team up on partial days, while others can explore solo, all with the comfort of sharing a guaranteed committed meal together every 24 to 48 hours.

because this maintains the feeling of camaraderie and connection without the drama of arguments, annoyances, and unnecessary sacrifices that stack up and end up ruining it for everyone.

Now, obviously with kids, you really don't have a choice. But if it's just you and one significant other, at worst, each person leads and follows on alternating days as big daily dues flip-flop in priority throughout the trip.

But okay, as promised, a speedrun of my own research best practices that work for me because I do still research, just differently.

Now, first, instead of plunging into a 100 top 10 lists, binging destination specific videos, I look first and foremost for patterns.

If the same cafe or street name keeps popping up for locals, bloggers, and upvoted comments, it's usually worth pinning.

Not necessarily committing to, but just adding to the custom map.

But I don't overdo specific research because nothing can beat on the ground spontaneity when you're in the middle of your trip.

For example, last year I went to a walkable street, turned a corner, and saw this huge lineup.

And honestly, this shackl looking stall did not disappoint.

It didn't show up in any of my initial research. And yet, if you see a ton of locals lining up, there's a darn good chance it's awesome.

I of course also research practicals like what time the transit system stops service every day? How much to expect to pay for a cab if I do stay out after the subway stops running? Are there specific cultural faux paws I should be aware of?

Specific areas to avoid because of either overcrowding my tourists or because they're a bit more crimeheavy.

What is a local emergency phone number since the 911 I'm used to here in Canada is not the same worldwide. That's it.

No spreadsheets, no daily itineraries with downto-theminute timestamps.

Just the practicals, the big daily dos to satisfy your selfish desired goals, a custom Google map to show options around each day's big daily do and the curiosity experience true exploration.

Looking back on literally hundreds of trips, I can't remember any of the overplanned ones, but I vividly remember the ones that were free flowing or even went wrong.

the day the restaurant I reserved was unexpectedly closed. So, I ended up sharing snacks with locals while playing chess with them instead.

Because that's the inevitable truth about travel.

You can never control everything.

But you can find joy as you discover anything.

So, plan the basics, pick your big daily do, and let the rest unfold.

Because when you stop trying to plan the perfect trip, you can finally start having the perfect trip.

And if you want to both download and see in field the custom Google map when I had just 24 hours in Tokyo a few months ago and how two big daily dues unfolded into the most fulfilling side quests, you will definitely want to watch this video right up here. If you're feeling lucky though, this video down here is the one for you.

I'll leave them both on screen for a few seconds so you can choose which one to watch next.

But while you're deciding, if you got value from this video, consider subscribing and hitting that bell so you'll be notified the moment new videos just like this one drop.