The Art of Wandering: Why Getting Lost Might Be the Best Travel Strategy
Posted: September 2016
Let’s be honest: not every trip needs a checklist. In fact, some of the best
ones don’t.
Sure, you can book tours, mark down every must-see landmark, and have Google
Maps guide your every step—but what if you didn’t? What if, just for a day, you
put away your schedule and let yourself get a little lost?
It’s not as scary as it sounds. In fact, it might be the most beautiful thing
you do on your entire trip.
Wandering Isn’t Wasting Time—It’s Making Space for Wonder
We’re conditioned to believe that a “successful” trip means seeing as many
highlights as possible. But rushing from one attraction to the next often
leaves little time to absorb what’s in between.
Wandering gives you the opposite: unscripted space, the kind that invites
small, unexpected moments—a local waving from a balcony, a hidden shop with
hand-bound journals, the smell of bread from a backstreet bakery you would’ve
never found otherwise.
When you wander, you let serendipity lead the way. And serendipity always has
better taste than a guidebook.
Some of the Best Stories Begin with ‘I Didn’t Mean To…’
“I didn’t mean to walk into that tiny bookstore, but I’m glad I did.”
“I wasn’t looking for a music bar, but the sound pulled me in.”
“I followed a cat through a gate and ended up at an open-air sculpture garden.”
Travel isn’t just about where you go—it’s about how open you are to being
pulled somewhere unexpected.
Art Lives in Corners, Not Just Galleries
As someone who constantly searches for beauty, I’ve learned that some of the
most inspiring art exists off the main path. It’s in murals hidden behind
alleys, hand-painted signage in old neighborhoods, and pottery studios with
creaky doors and no signage.
When you walk without a plan, your eyes start to scan differently. You stop
looking for “the big thing” and start noticing textures, light, movement, and
color in the quietest places.
Let the Locals Lead You Without Realizing It
If you want to wander with purpose, just follow the flow of locals. Walk in the
direction of foot traffic. Sit on a bench where old men play chess. Order food
from the stall with the longest line. Let people—without them knowing—guide you
toward authenticity.
You don’t need a sign that says “authentic experience this way.” You just need
to pay attention.
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How to Wander Well (Without Actually Getting Stressed)
Start early. Morning light is perfect, and shops start opening slowly.
Leave your phone in your bag (or use it only for photos).
Carry a small sketchbook or notebook for notes, doodles, or directions.
Follow the beautiful door, the open gate, the interesting shadow.
Eat when you’re hungry. Sit when you’re tired. Let your body guide you.
Drop a pin on Google Maps now and then if you're worried about getting too
lost.
Wandering doesn’t mean being careless—it just means releasing the need to know
what comes next.
You Can Wander in Your Own City, Too
This isn’t just travel advice. Try it at home.
Choose a neighborhood you’ve never walked through. Go out without an agenda.
You’ll be amazed at how different the world looks when you’re not rushing from
point A to B.
Your city has secrets, too.
Final Thoughts from a Side Street in Lisbon
As I type this, I’m
sitting in a tiny square I found by accident. The sun is slanting across
cobbled stone. A kid is kicking a soccer ball against a blue wall. There’s
music somewhere nearby. And none of this was planned.
I’ve seen the big sights already. But this—this moment of stillness and color
and life—is the one I’ll remember.
So wherever you go next, don’t forget to get lost. You might just find
something unforgettable.