A Walking Pilgrimage through Tuscany
Create space to see your life more clearly—and reconnect with what is true for you.
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.
September 2026
11 days / 10 nights | Limited to 6 women
Apply Now >
Schedule a Call >
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 eleven 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.
How This is Different
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.
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.
Ready to Take the First Step?
If this is resonating, you don’t need to have everything figured out before you begin.
We start with a short application and a conversation—to make sure this experience is the right fit for you.
Because this is a small, intentionally curated group, space is limited.
Apply for the September Retreat
Application takes ~10 minutes
Schedule a Call
A simple, no-pressure conversation
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.
How Coaching is Integrated
Each day includes multiple points of connection and reflection:
Morning — Intention Setting
We begin the day together over breakfast with a simple check-in.
You’ll be invited to notice what’s present for you and to carry a question or theme into the day’s walk.
These are not long sessions, but they create a clear starting point for how you move through the day.
On the Trail — Real-Time Coaching
As we walk, coaching happens organically.
Sometimes that looks like one-on-one conversation along the path.
Sometimes it’s a question, reflection, or moment of insight that arises in the experience itself.
Because you are in your life—not talking about it from a distance—the work tends to land more deeply and more honestly.
Evening — Reflection & Integration
At the end of each day, we gather for a short group reflection.
You may share a moment that stayed with you—something you noticed, a question that surfaced, or a shift in perspective.
These conversations are simple, grounded, and often unexpectedly meaningful.
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.
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.
Apply for the September Retreat
Application takes ~10 minutes
Schedule a Call
A simple, no-pressure conversation
Investment
September 17-27, 2026 · 11 Days / 10 Nights
Limited to 6 participants
$7,888 per person
A $1,500 deposit secures your place, with the remaining balance due in installments leading up to the retreat.
This includes accommodations (private rooms), daily luggage transfer, all breakfasts, lunches, and dinners, curated experiences, and individual and group coaching support before, during, and after the journey.
An optional wine package will be available for dinners, allowing you to enjoy regional wines each evening without needing to manage individual purchases or tabs.
This is the inaugural Pellegrina pilgrimage retreat, and pricing reflects this first offering.
Because this is a small, curated group, we begin with a short application and conversation to ensure it’s the right fit for everyone.
How to Apply
This is a small, intentionally curated group.
To apply, you’ll complete a short application so I can learn more about you and what’s bringing you to this experience.
From there, you’ll have the option to schedule a call if it feels helpful—to ask questions, talk through the experience, and make sure it’s the right fit.
Once accepted, a $1,500 deposit secures your place.
Ready toApply for the September Retreat
Ready toApply for the September Retreat
The Experience
This retreat is designed as a fully supported pilgrimage, allowing you to focus on the experience rather than the logistics.
Accommodations are arranged along the route, and your luggage is transferred ahead each day so you can walk with only a small daypack.
Meals are shared together whenever possible, creating space for conversation and connection at the end of each day’s walk.
Along the route we weave in experiences that reflect the culture and landscape of Tuscany.
These may include:
• wine tastings
• olive oil tastings
• time to explore historic Tuscan villages
• optional massage sessions
• moments for meditation and reflection
Transportation is arranged at the beginning and end of the retreat, and support is available along the route if needed.
Retreat Details
The Journey
-
This is a point-to-point walking pilgrimage along the Via Francigena in Tuscany.
Over the course of the journey, we walk from town to town, arriving in a new village or countryside property each evening. Your luggage is transferred ahead each day, so you carry only what you need for the walk.
The experience is steady, immersive, and grounded in movement—one step at a time through the Tuscan landscape.
-
Pilgrimage is different from traditional travel.
Rather than focusing on how much you can see or do, it invites a slower, more intentional way of moving through a place.
Historically, people have walked pilgrimage routes at moments of transition—when something is changing, ending, or asking for deeper reflection.
Walking day after day creates space—physically, mentally, and emotionally.
It quiets the usual noise and allows you to experience both the landscape and your inner world with more clarity and attention.
-
Yes — single accommodations are included every night.
-
Many women do! You’ll find instant companionship in the group while also having space for solitude.
-
Depending on which trail and how many walking days, we will walk 80-175 miles. The average daily distance is 12 miles.
-
Absolutely not! More than 40% of camino pilgrims are between the ages of 45-65. It will be important to train in advance for distances like these, but Pellegrina will provide a training plan to build your endurance and condition your body.
Preparation & Support
-
This is a point-to-point walking pilgrimage along the Via Francigena in Tuscany.
Over the course of the journey, we walk from town to town, arriving in a new village or countryside property each evening. Your luggage is transferred ahead each day, so you carry only what you need for the walk.
The experience is steady, immersive, and grounded in movement—one step at a time through the Tuscan landscape.
-
Pilgrimage is different from traditional travel.
Rather than focusing on how much you can see or do, it invites a slower, more intentional way of moving through a place.
Historically, people have walked pilgrimage routes at moments of transition—when something is changing, ending, or asking for deeper reflection.
Walking day after day creates space—physically, mentally, and emotionally.
It quiets the usual noise and allows you to experience both the landscape and your inner world with more clarity and attention.
-
Yes — single accommodations are included every night.
-
Many women do! You’ll find instant companionship in the group while also having space for solitude.
-
Depending on which trail and how many walking days, we will walk 80-175 miles. The average daily distance is 12 miles.
-
Absolutely not! More than 40% of camino pilgrims are between the ages of 45-65. It will be important to train in advance for distances like these, but Pellegrina will provide a training plan to build your endurance and condition your body.
The Journey
San Miniato
Gambassi Terme
San Gimignano
Colle Val d’Elsa
Monteriggioni
Siena
Ponte d’Arbia
Montalcino (Val d’Orcia)
The retreat concludes at a peaceful agriturismo near Montalcino, surrounded by vineyards and rolling hills.
Testimonials
From the Latin peregrinus, “traveler” or “wanderer”
Pilgrimage (noun)
A journey to a sacred place, taken on foot or in spirit, often across great distance, with the purpose of transformation.
Our walking retreats are not about reaching the end of the path.
They are about grounding yourself with every step.
copy
Coaching on the Path
Each day includes multiple points of connection and reflection:
Morning — Intention Setting
We begin the day together over breakfast with a simple check-in.
You’ll be invited to notice what’s present for you and to carry a question or theme into the day’s walk.
These are not long sessions, but they create a clear starting point for how you move through the day.
On the Trail — Real-Time Coaching
As we walk, coaching happens organically.
Sometimes that looks like one-on-one conversation along the path.
Sometimes it’s a question, reflection, or moment of insight that arises in the experience itself.
Because you are in your life—not talking about it from a distance—the work tends to land more deeply and more honestly.
Evening — Reflection & Integration
At the end of each day, we gather for a short group reflection.
You may share a moment that stayed with you—something you noticed, a question that surfaced, or a shift in perspective.
These conversations are simple, grounded, and often unexpectedly meaningful.
Walking the Via Francigena
The Via Francigena has been walked for centuries by travelers and pilgrims crossing Europe.
While the route has historic religious origins, this retreat is not religious. Instead, we approach pilgrimage as a personal journey — a way of stepping outside everyday routines and reconnecting with yourself.
Our route follows one of the most beautiful sections of the path through the Tuscan countryside before ending in the Val d’Orcia, a UNESCO World Heritage landscape known for its extraordinary beauty.