✈️ Travel Like a Pro (or at least fake it convincingly): My Secret Digital Toolbox
My 4th article on travel is about the tools I use to make life easy.
There are two kinds of travellers in this world:
Those who plan every hour of their trip six months in advance, down to when they will pause to feel grateful in front of a waterfall,
And those who remember at the boarding gate that they’ve booked two hotels for the same night, neither of which is refundable.
I used to be the latter. Now, thanks to a few trusty apps and the emotional scarring from an accidental night spent in a Slovenian bus station, I’ve evolved.
Here’s my not-so-secret digital toolkit for planning, managing, and surviving travel. You too can appear effortlessly organised, while secretly outsourcing all the hard work to a bunch of beautifully designed rectangles on your phone.
🧳 Wanderlog – For When You Want Your Trip to Look Like a Wes Anderson Film
Wanderlog is my main itinerary tool. Think of it as a digital corkboard where all your plans, dreams, dinner reservations, and confusingly named train stations come together in harmony. You can drag things around like a power-hungry dictator rearranging borders—except you're moving a visit to the Guggenheim from Tuesday to Wednesday.
Best part? It shows your trip as a beautifully linear timeline, so even if your life is chaos, your travel plans can look like a spreadsheet dreamed it was an art installation. It also has an optimise tool that optimises the daily itinerary for you.
Im such a big fan that I pay for the PRO version!!
🧾 TripIt – Because You Will Definitely Lose That Confirmation Email
TripIt is my Plan B. It's like that friend who remembers your birthday, your flight number, your hotel booking, and your irrational fear of middle seats. You just forward all your confirmation emails to it, and boom—TripIt turns them into a tidy little itinerary that makes you feel like you have a personal assistant.
Which, technically, you do. It just lives in your phone and never judges your midnight gelato habits.
💸 Splitwise – Avoiding That Post-Trip "Who-Owes-Who" Spreadsheet of Doom
Traveling with friends and family is a joy. Until someone says, “Wait, didn’t I pay for the last dinner?” and you realise you’ve been locked in a silent financial Cold War for 5 days.
Splitwise solves all of this. Every coffee, taxi, and questionable souvenir gets entered, and it magically tallies who owes what. No awkwardness, no calculators, no long-standing resentments over who ordered the extra guacamole. Those non drinking friends are saved from paying for their drunkard friends!! Yes we know who you are!!
You’ll still argue about directions, but at least not about money.
Another app that I pay for the Pro version - I don’t want to be limited to 5 expenses per day and also love the cool pro features.
🕵️♂️ TripAdvisor – For When You Want Advice from Exactly 9,342 Strangers
TripAdvisor is the peanut gallery of the travel world. I use it to decide where to go, what to eat, and whether that cute little inn is actually a thinly veiled front for a mosquito breeding program.
Yes, the reviews can be confusing (five stars: “Best pizza ever!!” next to one star: “They didn’t smile enough.”), but like all things in life, you learn to read between the lines.
If someone mentions the phrase “towels smelled funny” more than once, I’m out.
🏨 Booking.com / Hotels.com / Kayak / Airbnb – A Love Quadrangle
Let’s be honest: I don’t have loyalty. (I am biased to Marriott and Accor but they aren’t everywhere). Hence, I go wherever the best deal is, and I’m not ashamed. I’m the travel version of that person at the supermarket comparing six brands of peanut butter by protein content. Yes, my kids love the crunchy version!
These sites help me find 5-star experiences at 3-star budgets. And if I stare at them long enough, they start offering secret deals just to make me go away. Emotional manipulation? Maybe. But I got a sea view, so who cares?
✈️ Google Flights – The Spreadsheet of Dreams
This is the best tool for flight search. Period. You can track prices, see graphs, get alerts, and feel like a Wall Street analyst with very different priorities. I use it to find the cheapest dates to travel, and sometimes just to fantasize about escaping when the Wi-Fi stops working during a Zoom call.
Bonus: If you search long enough, Google will passive-aggressively remind you that prices are unlikely to drop further. Thanks, Google. You always know how to kill the vibe.
🌍 Polarsteps – For When You Want to Humblebrag in Map Form
There comes a point in every traveler’s life when simply posting photos on Instagram no longer scratches that wanderlust meets self-promotion itch. Enter Polarsteps—the app that turns your vacation into a cinematic travelogue, complete with a glowing red line showing where you've been, and a subtle "look-how-globally-experienced-I-am" undertone.
It automatically tracks your steps across countries, letting you relive your adventures and remember how many steps you took (both literal and metaphorical) to find that one bakery that had the good croissants.
Also useful if you ever need to prove to someone that you did, in fact, go to Slovenia, even though you mostly posted poolside pics from Croatia. No we didn’t do that!!
Bonus: At the end of your trip, it offers to turn your travels into a printed book; it adorns a place of pride on our coffee table. Take a look at our Balkans Trip!!
🧠 Final Thoughts from Gate 12
With these tools, I’ve managed to plan complicated international trips with minimal drama, no missed connections (well, almost), and only a few misunderstandings about hotel beds described as “intimate twin.”
Yes there are many people on twitter and instagram who use various othet tools but let's be real - most of us are happy with optimising.
So go ahead. Channel your inner travel ninja. With the right apps, you don’t need to be organised—you just need to look organised. Which, let’s be honest, is 90% of modern life anyway.
Want more of these practical-but-funny travel and life insights?
—it won’t organise your suitcase, but it’ll definitely lighten the mood.
Next week we talk about that one traveler…and how we can avoid being that person!!
Helpful article, Ramkey. TripIt and Wanderlog, will use them for my next trip.