Why AI Isn't the Answer to Planning Your Dream Trip

Open any app store and search for "travel planner." You'll see the same promise everywhere: Let AI plan your perfect trip.

It sounds efficient. It sounds modern. And I think it completely misses the point of why we travel in the first place.

The problem with outsourcing your adventure

Here's what AI trip planners get wrong: they treat planning as a problem to be solved. A chore to be automated away. Friction to be eliminated.

But planning isn't friction. Planning is where the trip begins.

Think about the last trip you were genuinely excited for. When did that excitement start? Not when you landed. It started weeks or months earlier—late nights falling down rabbit holes about the best neighborhoods. Conversations with friends about that restaurant they swore by. Screenshots saved. Lists made. Dreams taking shape.

That anticipation? That's not a bug in the travel experience. It's a feature. Maybe the best one.

What AI actually gives you

When an algorithm plans your trip, you get an itinerary. A list of things that are probably fine. Restaurants with good reviews. Attractions that are popular.

You know what you don't get?

• The tiny wine bar your coworker discovered on her honeymoon ten years ago
• The neighborhood that isn't in any guidebook but feels like the real city
• The restaurant you chose because the menu made you laugh
• The detour you made because something caught your eye

AI optimizes for efficiency and ratings. But the best travel memories rarely come from efficiency. They come from intention.

The case for intentional planning

I'm not saying planning should be painful. Nobody wants to wrestle with spreadsheets and scattered notes.

But there's a difference between removing friction and removing agency.

Good tools help you plan better—they don't plan for you. They give you a place to collect your ideas, organize your days, and see everything at a glance.

Where AI can actually help

AI is genuinely useful for certain parts of travel—just not the parts most apps are focused on.

AI is great for:

• Answering specific questions — "What's the best way to get from the airport to the city center?"
• Surfacing options you might have missed — "Are there any good day trips from here?"
• Optimizing logistics — "What order should I visit these places to minimize backtracking?"

Notice what these have in common: they're helping you execute on decisions you've already made. They're not making the decisions for you.

Travel is personal. Your planning should be too.

The trips I remember most vividly aren't the ones that were most optimized. They're the ones I cared most about while planning.

So by all means, use tools that make planning easier. Use AI when it genuinely helps. But don't let an algorithm turn your dream trip into a generic itinerary optimized for the average traveler.

You're not the average traveler. Plan like it.