I used to dread planning trips. The endless tabs, the indecision, the pressure to make it all “perfect”. I’d sit with a blank screen, a vague destination in mind, and zero idea where to start. By the time I booked anything, I’d already be tired of the trip I hadn’t taken yet.
What changed? It wasn’t some overnight transformation. But I slowly figured out what was making trip planning so frustrating and started doing things differently. The experience went from a burden to something I look forward to. If you’re like I was—someone who just wants to go but feels stuck in the planning stage—this might help.
Letting go of the “perfect trip”
The biggest mental block was trying to get every single thing right. Best flight, best hotel, best itinerary, best weather, best photos. I wanted to optimise everything. But travel doesn’t work that way. Things go wrong. Plans shift. Some places look better online than in real life. That’s okay.
Once I stopped trying to control every detail, I made room for small surprises. That’s when it got fun. I started leaving space in my days, saying yes to detours, and trusting I didn’t need a perfect plan to have a good time.
Starting with what matters to me
Instead of copying someone else’s itinerary, I asked myself, ‘What do I want out of this trip?’
Not what’s trending. Not what influencers say is a “must-visit”. Just—what’s my vibe right now? Some trips are for slow mornings and long dinners. Some are for exploring every corner of a new place. Once I figured out the mood of the trip, planning got easier. I didn’t need to do everything. I just needed to do what fit.
Tools that actually helped
At some point, I realised the tools I was using were making things harder, not easier. I was jumping between too many platforms, trying to compare everything manually. One day, a friend sent me a hotel link from Expedia, and I ended up planning the entire trip there.
Not trying to hype it up, but it was kind of a relief. I could see stays, flights, things to do, and reviews in one place. It cut down on all the second-guessing. I didn’t have to remember where I saw that one place or worry I was missing a better deal somewhere else.
I still use Expedia now and then, mostly for trips where I want everything organised neatly without extra effort. But the real point is: use tools that reduce friction, not add to it. If the process feels like a chore, something’s not working.
Finding rhythm, not rushing
When I started traveling more often, I noticed a pattern. My favourite trips weren’t the ones packed with activities. They were the ones with flow. Mornings where I could sit with coffee and people-watch. Evenings that ended with a spontaneous walk somewhere I hadn’t planned to go.
Planning now means building in rhythm, not just schedules. I give myself buffers. I overestimate travel time. I underplan some days on purpose. The beauty of it is that I come home feeling less like I checked off a to-do list and more like I actually lived somewhere for a while.
Recognising what drains me
This was huge. I used to think I just didn’t like trip planning. But the problem wasn’t the planning itself—it was the type of tasks that burnt me out. Scrolling for hours, comparing prices across six websites, calling places for availability… not my thing.
So I delegated. For some parts, I now rely on friends who enjoy the research phase. For others, I just use platforms that make the process quicker. Again, Expedia came in handy here too. Especially for those last-minute trips where I don’t want to start from scratch.
By knowing what part of the planning I disliked, I could take shortcuts that made sense.
Now, planning is part of the experience.
I didn’t expect to enjoy planning trips. But now, I almost need that part of the process to get into the travel mindset. It sets the tone. It gives me things to look forward to. And weirdly, I remember the feeling of planning certain trips almost as clearly as the trips themselves.
There’s also something satisfying about looking at the full picture—flights, places to stay, activities, all mapped out—and knowing it’s something I built. That it’s a trip shaped by my own curiosity and energy, not someone else’s guide.
Sometimes I still get stuck. Sometimes I still want to quit midway. But I’ve found my way through the noise. I’ve found tools that work for me, like Expedia, and I’ve stopped holding myself to some travel expert standard that never fit in the first place.
If planning your trip feels like a burden, step back and ask what’s really blocking you. It’s probably not the planning itself. It’s how you’re going about it. That shift changed everything for me.
And now? I already can’t wait to plan the next one.
