Planning vs Reality:
How Much Planning Is Too Much on a Trip?

Every trip starts with a plan. We try to think ahead, make good choices, and avoid the obvious mistakes. Sometimes it works. Sometimes it doesn’t. After travelling to many countries, we’ve learned that planning can be helpful, but it can also get in the way. Some of our favourite moments happened when plans changed, or when we didn’t really have one at all. This is just a few things we’ve learned about what planning can (and can’t) do once you actually arrive.

Chapters

Woman standing on a beach looking at the ocean, wearing white pants and a white top, with a small black bag hanging from her shoulder.

01
When Planning Felt Like Safety on Trips

When we first started traveling internationally, we planned everything.

Routes, accommodation, transport, daily activities, it all lived somewhere in a document or spreadsheet. Having a plan made unfamiliar destinations feel manageable. It gave us confidence before we’d earned it.

And honestly, at that stage, it helped.

Planning reduced travel anxiety. It gave structure to places we didn’t yet understand. It made travel feel possible instead of overwhelming.

But it also set an expectation: the plan was something to follow, not something to adapt.

The Brandenburg Gate, a neoclassical monument in Berlin, Germany, with a quadriga sculpture on top, against a blue sky with wispy clouds.

02
When the Travel Itinerary Became the Problem

Somewhere along the way, planning stopped feeling helpful and started feeling heavy.

Trips began to feel rushed. We’d leave places we liked earlier than we wanted because something else was scheduled. We stayed longer in places we didn’t love because we’d already booked accommodation. We felt guilty for resting because “we could be doing more.”

Nothing was technically wrong, but something felt off.

We realised we were prioritising the itinerary over how we actually felt in a place. The plan had become the goal, instead of the experience.

Scenic view of rolling hills with a farmhouse surrounded by tall, narrow cypress trees in the countryside.

03
When Trip Planning Truly Helps

We didn’t stop planning altogether, we just got more selective. There are situations where planning genuinely makes travel easier:

Logistics heavy destinations

Some countries or regions are harder to navigate. Transport runs infrequently. Distances look short on a map but take all day in reality. In these cases, planning saves time, money, and unnecessary stress.

Short or time-limited trips

When you only have a few days, having a rough structure prevents losing half the trip to indecision.

Accommodation in high-demand areas

Arriving tired and trying to “figure it out” rarely ends well. Booking the first nights or high-demand stays in advance saves frustration.

Planning works best when it removes friction, not when it dictates every move.

A scenic aerial view of a Mediterranean harbor town surrounded by hills with many colorful houses on the slopes. Several boats are docked along the waterfront.

04
When Planning Took Away Spontaneity

The effects of overplanning weren’t obvious at first.

We ignored our energy levels and pushed through days when we should’ve slowed down. We passed on spontaneous moments because they didn’t fit the itinerary.

Some of our least enjoyable travel days weren’t chaotic, they were simply overfilled and over planned. And some of our best travel memories happened on days with no plan at all. Flexibility isn’t the absence of planning; it’s leaving space within it.

A canal with a stone bridge over it, tightly packed historic buildings with gabled roofs lining the canal, bicycles parked along the railing, and cloudy sky overhead in Amsterdam.

05
What We Plan Now, and What We Don’t

Our approach today is simpler and less stressful.

What we plan in advance

• First accommodation in a new city or country
• Long-distance transport with limited options
• Visa related logistics
• Experiences we’d genuinely regret missing

What we leave flexible

  • • Daily sightseeing
    • How long we stay after the first few nights
    • Restaurants, cafes, and neighbourhoods
    • Most day trips

Our rule is simple:
Plan what would be stressful to sort out last minute.
Leave the rest open to reality.

Aerial view of a city skyline with tall buildings in the background, and a large park with trees, sports fields, and a river in the foreground.

06
The Travel Tools We Still Use (and the Ones We Don’t)

We still use tools, but differently.

Tools we rely on

  • Google Maps: saving places and offline navigation

  • Notes app: loose ideas, reminders, and backup plans

  • Booking platforms: checking availability and prices, not committing immediately

Tools we stopped using

  • • Hour-by-hour itineraries

  • • Overcomplicated spreadsheets

  • • Overloaded lists of “must-see” attractions

  • • Planning apps that require constant updates

Having more information didn’t make travel easier, it just made decisions harder.

A woman in a floral dress walking down a dirt road flanked by tall cypress trees during daylight.

07
How We Think About Planning Before a Trip

Before a trip, we ask ourselves a few questions:

  • What would cause stress if we didn’t plan it?

  • What can easily change once we arrive?

  • How much energy do we realistically want to have each day?

We plan just enough to feel grounded and leave room to adjust. Once we arrive, we reassess. Because no amount of planning fully survives reality.

A sailboat anchored in a turquoise bay near rocky cliffs, with patches of underwater rocks visible through the clear water.

08
What We’d Tell Ourselves at the Start

There’s no perfect amount of planning.

You’ll plan too much sometimes. You’ll plan too little other times. Both are part of figuring out how you like to travel.

Mistakes aren’t failures, they’re feedback.

The goal isn’t a perfectly optimized itinerary. It’s a trip that still feels good while you’re in it.

Planning should support your experience, not control it.

If it ever starts to feel like the itinerary matters more than the place, you’re probably planning too much.