Why Guests Come Back Again and Again: The Real Reason People Rebook a Retreat

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I used to think I was in the walking business.

CrossRoads Conversations

When I first started hosting Camino de Santiago walking retreats in rural Gascony, the French Tuscany, I assumed I would be the one doing most of the teaching.

I couldn’t have been more wrong.

Over the years, dozens of people have arrived at my farmhouse carrying backpacks, walking boots, and lives that had gradually become much too heavy. Some were still working. Some had retired. Some were rebuilding after loss, illness or divorce. Others simply couldn’t explain why they felt so restless.

They thought they had come to walk a couple of sections of the Camino.

In the end, they became MY teachers. The CrossRoads Conversations blog post series explores what my guests have taught me over the last twenty-odd years.

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After enough Camino de Santiago walking retreats along the Voie du Puy, I’ve had to quietly revise that. I’m not in the walking business. I’m in the business of letting people be someone slightly different for a week — and the walking, as it turns out, is just how we get there.

I noticed this properly years ago when a former guest, Sandrine, wrote to ask about coming back. Not for a different route, mind you — the exact same stretch she’d already walked. When I gently pointed this out, half expecting her to have muddled the details, she said something I’ve never quite stopped thinking about: “I don’t want to see something new. I want to be her again.”

She meant the version of herself who existed for those five days. More intentional. Less apologetic. The one who ate brunch without checking her phone first.

What I Thought I Was Selling

For years, if you’d asked me what guests were paying for, I’d have said: a well-planned route, decent food, farmhouse comfort, good company, maybe a touch of gentle challenge on the hills outside Eauze. All true. All, it turns out, beside the point.

What I’ve come to understand — slowly, and mostly by watching who rebooks and who doesn’t — is that the itinerary is just the scaffolding. It’s necessary, but nobody’s paying for the scaffolding. They’re paying for what the scaffolding lets them become, briefly, without an audience watching them.

I think this is why so few of my guests can tell me, six months later, exactly which villages they passed through. They remember a conversation over taboulé al fresco. They remember Loki, our rather opinionated Falabella, wandering over during brunch as if he had somewhere better to be and had decided brunch looked more interesting. They remember one sentence someone said, unprompted, on a grey Tuesday somewhere between Manciet and Nogaro. They almost never remember the schedule.

The Person Who Shows Up on Day One

Here’s what I’ve learned to watch for now, and it’s changed how I host entirely: the guest who arrives on day one is rarely the guest who leaves on day five, and the gap between those two people is the actual product.

I don’t say that to sound mystical about it — I was a doctor for a long time before any of this, and I’m allergic to that kind of talk. I mean it quite literally. Something about the rhythm of walking, eating, resting, and repeating — with no decisions more complicated than which trail marker to follow — seems to loosen a grip that people have been holding for years without noticing. By the time they leave, they’re not transformed exactly. They’re just… less braced.

And that’s the thing they come back for. Not Manciet. Not Nogaro. Themselves, the unbraced version, briefly available again.

Why I Keep Doing This

I’ll admit there are easier businesses than one built on four farmhouse beds and a handful of dates a year. But I’ve stopped apologising for staying small, because I think this particular thing — the letting-people-be-someone-else-for-a-week thing — simply doesn’t survive in bigger groups.

So if you’ve read this far and something in it landed a little too accurately — if you recognised yourself in Sandrine, or in the version of you that exists mostly in memory now — I’d genuinely like to hear from you. No booking form, not a sales funnel. Just write to me directly at MargarethaMontagu@gmail.com and tell me what brought you here. I read every email myself, and I’ll write back myself too.

Sometimes the most useful thing I can offer before you even decide whether to come is simply to ask: who is it you’re hoping to be again?