Why I Always Ask How You Want to Feel

Woman wrapped in blanket enjoys a peaceful ocean view with stunning sunset backdrop.

Founder Perspective

Why I Always Ask How You Want to Feel

Most travel planning begins with a destination. A country someone has always wanted to visit, a hotel seen in a magazine, a friend’s recommendation passed across a dinner table. Those are perfectly good starting points. But in fifteen years of designing journeys for people, I’ve learned that the destination is rarely the real answer to what someone is looking for.

So I always ask a different question first.

How do you want to feel?

The answers are more revealing than people expect. Relaxed — which sounds simple, but means something different to everyone who says it. Some people relax beside a pool with a novel. Others relax when every logistical detail has been removed from their field of vision. Others relax only once they’ve moved their body — a long walk, an early swim, a hike that earns the view. Relaxation is not a single thing. It requires understanding the person.

Energised is another common answer — and one that immediately tells me something important. An energised traveller doesn’t want four nights in the same hotel. They want sequence and variety and the particular pleasure of arriving somewhere new with a full day ahead of them. They want the pace of the journey to match their own pace, not the pace of the itinerary template.

Able to switch off is the one that makes me listen most carefully. Because it usually means something isn’t working at home, and the trip is carrying more weight than a holiday should have to carry. When someone needs to truly disconnect — from work, from noise, from the version of themselves they’ve been for the past six months — the planning conversation changes entirely. The right property matters more. The itinerary needs more space in it. The excursions need to be chosen rather than accumulated. I find myself thinking not just about where they should go, but about what they should leave behind when they get there.

And then there is the answer I think about most often.

Find me.

It arrives occasionally, and always quietly — sometimes not quite in those words, but unmistakably in that spirit. Someone who has been so thoroughly occupied by their life — their responsibilities, their roles, their relentless forward motion — that they’ve lost a sense of who they are when nobody needs anything from them. They want to travel not to collect experiences, but to remember something.

That is not a brief I can answer with a hotel recommendation. It requires a conversation. Several, sometimes. What did they love before everything got complicated? What kind of morning do they wake up to in their best imagination? What does a day feel like when it belongs entirely to them?

The itinerary that comes from those conversations looks different from the ones that begin with a destination. It has more stillness in it. More space between things. More intention behind every choice. It’s designed not to fill the time but to return something — a slower pace, a sense of self, the quiet pleasure of being somewhere beautiful with nothing required of you.

This is why I ask the question. Not because the destination doesn’t matter — it does, enormously — but because the destination is where the journey takes place. The feeling is what you carry home.