Walking Retreat in Tuscany
April 7-17, 2027
10 nights in Tuscany | Limited to 6 women
Walk the Via Francigena from town to town—through villages, countryside, and quiet stretches of the Tuscan landscape—with space for reflection, meaningful conversation, and integrated coaching along the way.
Leave the busyness, the demands, and the expectations behind. So you can hear yourself again and return to what feels true.
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A different kind of retreat
There are many beautiful retreats in Italy. There are also many people who walk the Via Francigena.
But this is something else.
More than simply a retreat in Italy, a guided walk on the Via Francigena, or a group coaching experience— Pellegrina’s walking retreat offers pilgrimage with integrated coaching, set within the beauty and richness of Tuscany and shared with women who are seeking space, clarity, and a deeper connection with themselves.
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Itinerary
Day 1
Arrival in Florence
Day 2
San Miniato
Day 3
Walk: San Miniato to Gambassi Terme
Day 4
Rest: Gambassi Terme
Day 5
Walk: Gambassi Terme to San Gimignano
Day 6
:Walk: San Gimignano to Colle di Val d’Elsa
Day 7
Walk: Colle di Val d’Elsa to Monteriggioni
Day 8
Walk: Monteriggioni to Siena
Days 9-10
Walk + Rest: Siena to Buonconvento
Day 10
Departure
View the full details here.
What is Pilgrimage?
Pilgrimage has long been a way people step outside of everyday life—often at moments of transition—to reflect, reset, and reconnect with what matters most.
Unlike traditional travel, pilgrimage is not about seeing more or doing more.
It’s about moving with intention.
Paying attention.
Allowing the experience itself to shape what you notice, what you feel, and what begins to shift.
There isn’t a single reason people choose to walk a pilgrimage route.
Some arrive with a question.
Some are in the midst of change.
Some simply feel the need to step away and create space.
Having it all figured out before you begin would miss the whole point.
It’s the act of walking itself—day after day, step by step—that begins to quiet the noise and create space for something deeper to emerge.
The Experience
This is a pilgrimage with integrated coaching—a journey that combines the physical experience of walking through Tuscany with space for reflection, conversation, and meaningful connection.
This journey follows a section of the Via Francigena, an ancient pilgrimage route that has connected Canterbury to Rome for over a thousand years. For centuries, travelers have walked these same paths—moving through the landscape on foot, passing through villages, and following a route shaped by time, movement, and human experience.
Pilgrimage has long been a way people step outside of everyday life—often at moments of transition—to reflect, reset, and reconnect with what matters most.
Today, the route remains remarkably intact.
You are not simply walking through Tuscany—you are walking along a path that has been traveled for centuries, one that invites a different pace, a different kind of attention, and a deeper experience of place.
Over ten days, we walk from town to town along the Via Francigena, moving through vineyards, olive groves, wooded paths, and open countryside. Each day brings a new landscape, a new village, and a new place to land at the end of the walk.
There’s a simplicity to the structure of each day—walk, arrive, rest, share a meal—that begins to quiet the noise of everyday life.
You carry only what you need for the day. Your luggage is transferred ahead each morning. Breakfast is shared before setting out, and dinner brings the group back together each evening.
Along the way, we pause.
For coffee in small village cafés. For long lunches along the route. For wine and olive oil tastings with local producers. For moments of quiet, where the landscape itself invites you to slow down and take it in.
Some days are more physically demanding. Others offer time to rest, recover, or linger. One afternoon, we’ll visit a local spa with a sauna, heated pools, and the option for massage.
We stay in a mix of boutique hotels, agriturismos, and locally owned properties, each chosen for its character, comfort, and connection to the surrounding area.
Every room is a private, single room—offering space to rest, reflect, and fully take in the experience of the day.
This is a small, intentionally curated group, and I will be walking the full route with you—supporting both the logistics and the deeper experience along the way.
This is not a rushed itinerary.
We are not trying to see everything.
Instead, we move steadily through the landscape, allowing the experience to unfold one step at a time.
Walking this way changes how you experience a place.
It also changes how you experience yourself within it.
Limited Space Available – Reserve Your Spot Today
Limited Space Available – Reserve Your Spot Today
What Happens When You Walk
There’s something about walking day after day that begins to shift how you experience things.
The pace is different. Your attention changes.
What felt urgent or loud at home starts to quiet.
Without trying to force anything, you may begin to notice things more clearly—your thoughts, your patterns, what feels aligned and what doesn’t.
Time feels less compressed.
There is space to think, but also space not to think—to simply walk, observe, and be present.
Some moments are social and connected, while others are quiet and internal. Both are part of the experience, and both can bring something into focus—a simple but meaningful sense of clarity.
Perhaps more than anything, the repetition of walking for many hours, over many days in a row, begins to settle you into presence—and into the peace that can come with it.
Click here to view the full retreat details.
Before & After the Walk
This experience doesn’t begin when you arrive in Italy—and it doesn’t end when you leave.
In the weeks leading up to the retreat, you’ll receive guidance and support to help you prepare—physically for the walk, and personally for what you’re stepping into. We’ll begin to get clearer on what’s bringing you here, and what you want to be paying attention to along the way.
After the retreat, we continue with integration support—helping you make sense of what shifted and how it fits into your life.
Not to give you more to do, but to create space for what you’re ready to integrate now that you’re home.
Because the value of a pilgrimage isn’t just what happens while you’re away—it’s also what you carry forward into your life.
Why You Might Be Drawn to This
Something in you may already know why this is calling to you.
More often, women feel drawn to this kind of journey because they want a different kind of experience—one that allows them to slow down, pay attention, and reconnect with themselves in a more honest way.
Not to escape life, but to return to it differently.
There are seasons when that kind of pause matters more than answers.
And pilgrimage offers a way into that—through movement, through rhythm, and through the experience of walking day after day, without needing to force anything.