A Case for "Winging It" While Traveling
Rigid planning has always been a recipe for disaster for me. What happens when the landmark you’ve built your whole day around turns out to be a dud? Your plans become a prison, and you miss better things waiting just around the corner.
I’ve had a different approach throughout my life. One that goes with the flow and lets my whims take me where they may. If your lifelong dream is to see the pyramids, by all means, plan the trip. But if you’re somewhere new without expectations, forget planning and just… go. This isn’t for people with bucket-listers. This is for the rest of us. Those of us chasing something authentic, not a tourist trap.
When I visited Edinburgh, the decision to go to a restaurant called Dishoom was a non-decision. It was just a name on a map that caught my eye. A virtual coin toss in a city I didn’t know. I didn’t check any reviews. I followed a whim.
The moment I stepped inside, the churn of the Royal Mile melted away. The décor felt… real. Humming with Indian aesthetics, it was a world apart from the tartan and bagpipes outside. It felt like a discovery. Sure, I found out later it’s actually a famous chain restaurant that my Westernized lizard brain had never heard of, but, in the moment, that didn’t matter. I’d walked in blind, and that made the experience mine.
And then they brought the Chai. My first time having it, I think. And it was… perfect. The meal was the right one in that moment. It made the day. And as someone who enjoys food, it’s one of my fondest memories of the entire trip.
That’s the magic of a spontaneous discovery. It feels earned. The moment you stumble upon yourself has a weight that no scheduled photo-op can match. The problem with an itinerary isn’t just that it’s boring. It cages you. It walls you off from serendipity, from the better stories waiting if you give yourself the chance to see them.
So no, I don’t have a checklist for you. I don’t have a Top 10 list. The only advice I can give is this: leave it to chance. Try traveling with an un-itinerary.
Trust the power of a whim. See where the day takes you. You might end up with fewer photos for your feed, but you’ll leave with stronger, more personal, more honest memories. And isn’t that the point?
