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What Really Matters When You Travel (and What Doesn't)

Writer: Jenny O
Jenny O
Sep 8
3 min read

Updated: Sep 16

I've planned so many trips by now, both for other people and for myself, that there's one thing I can say with certainty: the best trip is rarely the one with the longest list of sights. After Mexico, Hawaii, Sri Lanka and Thailand — to name just a few — it's become clearer and clearer to me what really matters. And it's not what most travel blogs tell you.


It's Not About the Number of Countries, But the Depth of the Experiences

It's tempting to pack a trip with as many stops as possible — three countries in ten days, a new hotel every day, a new item on the itinerary every morning. I've done that myself, and I ended up more exhausted afterward than before the holiday. The trips I actually remember are the ones where I gave a place time: a fishing village in Thailand where I stayed three days instead of one night, because the owner of my accommodation invited me to dinner with her family. You won't find that in any guidebook.



The Most Underrated Travel Tip: A Day With No Plan

When I plan a trip today — for myself or for you — I deliberately build in at least one day with no fixed program. No excursion, no reservation, no guide. In my experience, it's exactly on these days that the unexpected happens: an invitation, a café you end up lingering in, a beach you won't find on any map because you stumbled upon it while out for a walk. Fully planned trips feel safe — but the memories are often made exactly where the plan stops.


Why the Most Expensive Hotel Rarely Gives You the Best Memory

I've stayed in five-star resorts and in simple guesthouses with cold water. Honestly, I remember the guesthouse in Panama, whose owner explained to me every morning which fruits were in season, far more vividly than any hotel lobby with marble floors. Luxury has its place, no question — but it's no substitute for real contact with a place. That's why, when planning a trip, I always ask: what actually matters to you in your budget — comfort or experience? It's usually worth saving where it's only about prestige, and investing where it's about real experiences: a private tour with a local guide, a cooking class, an excursion off the tourist routes.


Local People Instead of Just Local Sights

The sight is usually the reason you fly somewhere. But the encounter is usually the reason you still remember it years later. A short conversation with the fisherman showing you his catch on the beach, a recommendation from your host for the restaurant that isn't on Google Maps — moments like these can't be booked, but you can make room for them by traveling more slowly and asking more often instead of just taking photos.


Flexibility Beats Perfection

And then there's the whole thing with overcrowded hotspots. I've experienced firsthand how disappointing it can be to queue for the "perfect" sunset spot like you're at a supermarket checkout. My experience: whoever is willing to choose the second-most-famous place instead of the most famous one often gets the better experience — fewer people, more peace, more genuine moments. That's also one of the reasons why, when planning a route, I almost always build in an alternative to "the number one on every list."


My Takeaway


A good trip isn't measured by how much you saw, but by how much you took away from it. That's exactly why, with every trip I plan, I don't just ask "Where do you want to go?" but also "How do you want to feel at the end of the trip?" The answer to that decides the route — not the longest list of sights. If you feel like your next trip should be more than a checklist of ticked-off points on a map: that's exactly what my travel planning is about.


Ready for your next adventure?



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