5 Adventures AI Couldn’t Plan (And Why That Matters)

I’ll start with a small confession.

In some shape or form I use AI almost every day. It helps me research, structure ideas, sharpen thinking and move faster on the admin that would otherwise eat into creative energy. In many ways, it’s an extraordinary tool.

And yet — the more I use it, the more convinced I become that the most meaningful adventures in the world still can’t be automated.

Not because AI isn’t clever. But because adventure isn’t a data problem.

Algorithms are brilliant at optimising for price, popularity, convenience and efficiency. They’re very good at finding the “best” version of what already exists. What they struggle with is everything that makes transformational travel… well, transformational: nuance, uncertainty, human chemistry, weather windows, judgement calls, personal readiness, cultural sensitivity, slow magic.

Adventure doesn’t live in filters. It lives in friction, trust, timing and the quiet moments you couldn’t possibly predict.

Here are five types of journeys no algorithm could ever truly plan — and why that’s exactly why they matter.

1. A Tall Ship Ocean Crossing

Ask an algorithm to plan your transatlantic journey and it will reliably serve you up the fastest flight, the best airline reviews, and the most efficient transfer.

It will never suggest spending three weeks crossing an ocean under sail.

Why? Because there’s no metric for the things that actually make an ocean passage powerful: how you respond to long horizons, how you cope with discomfort and boredom, how you bond with strangers on night watch, how your nervous system settles when the only agenda is wind and weather.

AI can’t assess your temperament for motion, your appetite for learning seamanship, your emotional readiness for disconnection, or your quiet joy in doing something slow and analogue in a hyper-digital world.

Those judgements still require human conversation, lived experience and intuition.

2. Living With Reindeer Herders in Northern Mongolia

Algorithms love certainty. Nomadic life offers none.

Living alongside reindeer herding families in Mongolia’s taiga means adapting to weather, animals, food availability, language barriers and cultural rhythms that don’t run on clocks or calendars. Some days unfold beautifully. Some days are hard. Most days are unpredictable.

There’s no algorithm that can tell you whether you’ll thrive in silence, whether you’ll find joy in simplicity, whether you’ll adapt gracefully when plans dissolve, or whether you’ll feel comfortable being a guest in someone else’s ancient way of life.

AI will happily suggest a luxury eco-lodge instead. But it can’t understand the value of being slightly uncomfortable in the service of genuine human connection and perspective shift.

3. A Long Overland Journey Across Africa

From a data perspective, long overland travel makes very little sense. It’s slower than flying. Less predictable. Less comfortable. Harder to neatly summarise in a review score.

And yet, spending weeks crossing a continent by road quietly changes how you experience time, place and people.

You stop rushing. You stop counting days. You learn patience. You learn to share space, solve small problems together, accept uncertainty and appreciate gradual transitions rather than instant gratification.

No algorithm can measure group chemistry, resilience, humour, adaptability or the psychological arc of long-form travel. It doesn’t understand that the journey itself becomes the medicine.

4. A Citizen Science Sailing Expedition

Ask AI to plan a sailing holiday and it will optimise for comfort, amenities, Instagrammability and convenience.

It will not understand why someone might choose to tow a plankton net at dawn, log whale sightings, collect microplastic samples or contribute to long-term ocean research — simply because it feels meaningful to be useful.

Purpose, contribution, stewardship and quiet satisfaction don’t fit neatly into recommendation engines. There’s no rating system for “this made me feel part of something bigger than myself.”

Those motivations live in values, not algorithms.

5. A Weather-Led Arctic or High Latitude Expedition

High latitude expeditions operate in a world that algorithms fundamentally dislike: uncertainty.

Routes change with ice conditions. Landings shift with weather windows. Wildlife encounters can’t be scheduled. Leadership judgement matters more than itinerary promises.

AI prefers guaranteed outcomes. Adventure lives in adaptive decision-making, experience-based judgement and trust in human leadership when conditions evolve.

The magic of these journeys often lies in what doesn’t go according to plan — and how the group navigates that together.

What This Really Says About Travel (And About Us)

This isn’t an argument against technology. It’s a reminder of where technology reaches its limits.

AI is excellent at helping us move faster, cheaper, easier and more efficiently. But the most powerful travel experiences rarely live at the end of those filters.

They live in slowness, complexity, uncertainty, human relationships and environments that can’t be neatly optimised.

Adventure still needs human judgement.
It still needs storytelling.
It still needs trust.
It still needs people who understand nuance, readiness, temperament and timing.

And perhaps most importantly — it still needs room for surprise.

In a world increasingly shaped by algorithms, choosing experiences that resist optimisation may be one of the most quietly radical things we can do.

Curious which kind of un-optimisable adventure might stretch and restore you next?

That conversation still starts best with a human.