ITALY | Spring 2027 | WAITLIST

Enneagram Spirituality and the Franciscan Way

Ian Morgan Cron
Bestselling author ofThe Road Back to You and Chasing Francis

In Spring 2027, I'm leading a small group to Italy — to the places where Francis of Assisi lived, prayed, and was transformed. We'll move slowly, with daily teaching, shared meals, and the kind of unhurried conversation that the pace of ordinary life rarely allows. The Enneagram will be a companion lens throughout the journey. Details are coming. I wanted you to hear about it first.

I'm Interested

Why a Pilgrimage?

The Journey of St. Francis

St. Francis of Assisi found me in a season of my life when almost everything I thought I knew about faith was coming apart. He didn't hand me a theological system. He showed me a different way of moving through the world — slower, more attentive, more honest about what I was actually carrying.

For years, I've wanted to lead a pilgrimage through a similar journey. To walk where Chase walked. To stand in the places where Francis of Assisi lived, prayed, and changed. Not because the places themselves are magic — they're not — but because something about standing in them, slowly, with other people asking the same kinds of questions, does something that reading alone can't. I still don't fully understand what that something is. I just know it's real.

So I'm going. And I'd like you to come with me.

The Enneagram will be woven into the teaching throughout the week. Not as the main event, but as a companion — a way of helping each person understand what they're encountering in Francis's story and in themselves. I've found that the two illuminate each other in ways I'm still learning from.

I'm still working out the final details — dates, itinerary, all of it — and I want to get it right before I say more. If you've carried Chasing Francis for a long time and feel like you're ready for what comes next, I hope you'll put your name on the list.

I'll be in touch soon.

— Ian

"The geographical pilgrimage is a symbolic acting out of an inner journey.

– Thomas Merton

What I'm planning

A Pilgrimage, Not A Tour

Daily teaching

Each day I'll teach on a theme from Francis's life — simplicity, poverty, beauty, suffering, joy — and what it has to say to us today. The Enneagram will surface as a companion lens throughout the week, woven into the teaching rather than standing apart from it.

Sacred Franciscan sites

We'll walk the geography ofChasing Francis— the sites that shaped both Francis of Assisi and the book. I'll be there to walk them with you, and to connect what we see to what we're learning.

A small, intentional group

I'm keeping this deliberately small. The intimacy of a small group isn't incidental — it's the point. The Enneagram work is more honest, and the pilgrimage more meaningful, when everyone knows they're among people taking it seriously.

I'll be there the entire time

I'll be present for the full journey — teaching in the mornings, walking in the afternoons, at the table in the evenings. This isn't a trip where I show up for a session and disappear.

Italy in Spring

I chose spring in Italy deliberately. The landscape is extraordinary, the pace feels right, and the light in May is unlike anywhere I've ever been.

Space for silence

I've built in room to walk alone, to journal, to sit in a church without an agenda. The Enneagram work and the pilgrimage both require some quiet — and I want to protect that.

What Others Have Said About The Books

  • LORD ROWAN WILLIAMS | Former Archbishop of Canterbury

    I’ve now read Chasing Francis twice and found it equally compelling both times. It is challenging, disarming, and delightful, and the vision behind it is a serious one. It’s a remarkable book.”

  • RUTH HALEY BARTON | Founder of the Transforming Center

    The Road Back to You is a fresh, insightful, and winsome introduction to the Enneagram. Ian Cron provides a wise and compassionate guide to self-understanding.

  • FR. RICHARD ROHR | Author of Falling Upward

    Ian Cron does it again, but with real insight, imagination, and courage. Join in the chase!

  • SHAUNA NIEQUIST | Author of Present Over Perfect

    A wonderful story of pilgrimage and redemption...rich, bursting with details and insights, full of wisdom and warmth.

“St. Francis taught me that if we spent less time worrying about how to share our faith with someone on an airplane and more time thinking about how to live radically generous lives, more people would start taking our message seriously.”

– IAN MORGAN CRON

Join the Waitlist