I have been, for most of my adult life, an over-planner of travel. Detailed itineraries, researched restaurants, booked activities — the trip planned before leaving home, with enough structure that surprises were minimised and the daily experience was essentially executing a document I'd written weeks earlier from the comfortable remove of my regular routine.
The problem with this approach is not that planning is bad — it's that planning optimises for avoiding negative experiences rather than maximising positive ones, and these are not the same thing. A well-planned trip eliminates most of the things that can go wrong. It also eliminates most of the things that can go unexpectedly right.
The unexpected right things are where travel's most memorable experiences tend to live. The conversation with a stranger that changes your understanding of a place. The neighbourhood you wandered into without a purpose that turned out to have more genuine character than the famous street three blocks over. The meal you chose because you were hungry and it was nearby, rather than because a review said it was the best of its type in the city — that often turns out to be the meal you tell people about afterward.
I started experimenting with deliberate underplanning about two years ago, beginning with a short trip where I booked only accommodation and left everything else genuinely open. The discomfort of this was real — particularly on day one, when the lack of a plan produced a low-grade anxiety that I recognised as the instinct to know what was happening before it happened.
By day three, the anxiety had been replaced by something considerably better. Reading travel content that discusses this balance honestly helped me understand that the planning instinct is partly about control and partly about genuine preparation — and that the useful parts of preparation (knowing the practical logistics, having safety information, understanding basic cultural context) are much smaller than the typical over-planned itinerary implies.
The lifestyle shift required to travel this way is real but not large. It's primarily about tolerating uncertainty for longer before resolving it into a plan, and about trusting that interesting things will happen without having been specifically scheduled.
The trips I've taken with this approach have produced experiences worth writing about in ways that the meticulously planned ones rarely do. The difference isn't the destination — it's what you allow to happen once you arrive.
Top comments (0)