A Walking Pilgrimage Through Tuscany
Leave the busyness, the demands, and the expectations behind. So you can hear yourself again and return to what feels true.
Walk the Via Francigena from town to town—through vineyards, olive groves, and quiet stretches of the Tuscan countryside—with space for reflection, meaningful conversation, and integrated coaching along the way.
September 2026
10 days / 9 nights | Limited to 6 women
Interested in learning more? Let's talk and we can explore whether this is the right experience and the right timing for you.
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.
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.
Day-by-Day Journey
Day 1 — Arrival in San Miniato
You’ll arrive in Florence, where you’ll meet up with me and your fellow pellegrinas. A private car will drive us into the Tuscan countryside—rolling hills, cypress trees, and small hilltop villages beginning to set the tone for what’s ahead.
We’ll settle into San Miniato, a historic town known for its food culture, white truffles, and roots in the Slow Food movement.
After time to rest and settle into your private room, we’ll gather for a short welcome before walking together to dinner—an unhurried, beautifully prepared Tuscan meal to begin the journey.
Day 2 — San Miniato to Gambassi Terme
Our first walking day.
We leave San Miniato in the morning and make our way through countryside and steady climbs toward Gambassi Terme, eventually arriving at a peaceful hilltop estate just outside the village.
Dinner is shared on-site—simple, local, and deeply satisfying after a full day on the trail.
Day 3 — Arriving Fully
After yesterday's walk, we pause.
The body gets a chance to recover. The mind begins to quiet. And having spent the first day on the trail together, the group settles into a different kind of time together—through guided conversation, intention setting, and the beginning of deeper connection.
There's also space for solitude—to wander the estate, journal, or simply take in the sweeping views across the Tuscan valley to the snow-capped Appennini.
A day to land—in the group, in the landscape, in yourself.
Day 4 — Gambassi Terme to San Gimignano
Today, we’re back on the trail.
We walk through vineyards and open countryside, stopping mid-morning for an olive oil and wine tasting with a local producer.
By early afternoon, we arrive in San Gimignano—known for its medieval towers, local saffron, and Vernaccia white wine.
There’s time to explore, wander the streets, visit small shops, or sit in the piazza.
And for those who want to, a stop for gelato at the well-known Gelateria Dondoli.
Day 5 — San Gimignano to Colle di Val d’Elsa
A steady walking day brings us to Colle di Val d’Elsa.
In the afternoon, we slow things down with time at a local spa—sauna, heated pools, and the option for massage. A chance to rest the body and absorb a few days of movement.
Day 6 — Colle di Val d’Elsa to Monteriggioni
Today’s walk follows stretches of the Elsa River, with sections of trail that feel quieter and more immersed in nature.
We arrive in Monteriggioni, a small, walled medieval village that feels almost untouched by time.
The afternoon and evening are unhurried—time to explore, rest, and gather again over dinner.
Day 7 — Monteriggioni to Siena
We continue toward Siena, one of Tuscany’s most historic and architecturally rich cities.
After settling in, we’ll walk through the Piazza del Campo and past the Duomo—taking in the scale and beauty of the city—before dinner together.
Days 8-9 — Siena to Ponte d’Arbia
On our sixth and final walking day, we continue south along the Via Francigena, moving deeper into the Tuscan landscape.
We arrive in Ponte d'Arbia, in the Crete Senesi region south of Siena—a landscape known for its expansive views, winding roads, and quiet beauty.
We'll spend two nights here at a family-run agriturismo. The full day at the end of our journey gives us time to rest our bodies, reflect on our accomplishment and the insights that arose along the way, and begin integrating the experience of the walk—individually and together.
Day 10 — Departure
A group transfer will return us to Florence at a set time that morning. From there, you can continue home or spend additional time in Italy on your own.
An optional add-on day is also available—an additional guided day in Tuscany to extend the journey before returning home.
After days of walking, conversation, and reflection, this is where the pilgrimage comes to a close.
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.
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.
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.
Let's explore whether this walk is for you.
An unhurried conversation — about where you are, what's calling you, and whether this retreat is the right one. No application to fill out first, no pressure to decide anything. Just a chance to feel it out together.
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.
Is This the Right Retreat for You?
Investment
September 17-26, 2026
10 Days / 9 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. The women who walk it this first year are part of something at its beginning — and the current price reflects that. Future retreats will be priced higher.
How to Apply
We start with a conversation.
This is a small group — six women — and the right fit matters, for you and for the group as a whole.
So we begin with a conversation. An unhurried call to talk about where you are, what's drawing you to this walk, and whether this is the right experience and the right timing for you. There's nothing to prepare and nothing to commit to — it's simply how we both find out if this is a yes.
If it feels right after we talk, you'll complete a short application, and a $1,500 deposit secures your place.
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.
-
We will walk for 6 consecutive days and daily distances range from approximately 8 to 17 miles (14–26 km).
The terrain includes:
– dirt and gravel paths
– vineyard and farmland roads
– wooded trails
– occasional paved sectionsThere are also elevation changes throughout, including steady climbs and descents.
-
This is a physically active experience.
Participants should be prepared for 6–10 hours of walking per day (including breaks) and multiple consecutive days of movement.
Though it does require endurance, preparation, and a willingness to be physically engaged, we each walk at our own natural pace, frequently checking in with ourselves on what feels best in the moment.
-
Each day unfolds at a natural, steady pace.
There is space to walk alongside others, as well as time for quiet and solitude along the path. You are encouraged to walk at your own natural pace.
We regroup at natural stopping points throughout the day and always arrive together by the end of each walk.
-
You are never too old—or too young—to go on pilgrimage.
Many people who walk routes like the Via Francigena are in midlife and beyond, with the majority of walkers in their 40s, 50s, and 60s, and a growing number in their 70s as well.
Preparation & Support
-
Preparation is an important part of the experience.
– If you currently walk 3+ miles comfortably several times per week, plan for 8–12 weeks of training
– If you are newer to longer walks, plan for approximately 4 months of preparationYou will receive a custom walking training plan after registration.
We also recommend consulting with your physician prior to the retreat to ensure this level of activity is appropriate for you.
-
To support you in preparing for the journey, you’ll receive:
– A custom walking training plan
– A detailed packing list, with specific product recommendations
– Guidance on gear, footwear, and daily essentials
– Preparation materials to help you arrive ready—physically and mentally -
Before the retreat, we’ll gather for two virtual group calls: one for Q&A and one for exploring our intentions for the pilgrimage.
This is a chance to:
– meet the other women in the group
– ask questions
– review logistics and expectations
– begin setting intentions for the experience -
In the months leading up to the retreat, each participant will be able to schedule two individual coaching sessions with Katherine to explore personal intentions, etc.
Additionally, you’ll have access to support for training, preparation, and logistics-related questions as you get ready for the journey.
Accommodations, Food & Wine
-
We stay in a curated mix of boutique hotels, agriturismos, and Tuscan villas, each selected for its comfort, character, and connection to the surrounding landscape—from restored countryside estates to small, locally owned properties.
All participants have private, single rooms, offering space for rest, quiet, and integration at the end of each day.
-
Daily breakfast, dinner, and most lunches are included.
Meals reflect the region—seasonal, local, and rooted in Tuscan tradition.
– Breakfast is typically served at your accommodation
– Lunch may be enjoyed at a café or as a packed meal along the route
– Dinner is shared together each evening -
The optional wine package includes wine with group dinners throughout the retreat, featuring regional selections appropriate to each location. This allows for a more seamless experience without needing to manage individual orders or payments.
Curated Dinner Wine Package — $495
Includes a selection of regional wines served with group dinners. -
We do our best to accommodate dietary needs and restrictions. Please share any requirements during the application process so we can plan accordingly.
Experiences Along the Way
-
Select experiences are woven into the journey to deepen your connection to the region:
– Wine and olive oil tastings with local producers
– Time in historic towns such as San Gimignano and Siena
– A spa experience with sauna, thermal pools, and optional massageThese experiences are intentionally spaced throughout the retreat, allowing them to enhance—not interrupt—the rhythm of the walk.
-
There is space built into the itinerary to wander, rest, and experience each place at your own pace.
This may look like:
– exploring a village in the afternoon
– sitting in a piazza with a coffee or glass of wine
– resting at your accommodation -
Coaching is woven into the rhythm of each day.
Through morning reflections, on-the-trail conversations, and evening integration, you’ll have ongoing support as you move through the experience—allowing insights to be explored in real time—while you are in the experience, not just after the fact.
What’s Included & Not Included
-
– 9 nights accommodations (private rooms throughout)
– Daily breakfast, dinner, and most lunches
– Luggage transfer between accommodations
– Private group transfer from Florence on arrival day and return transfer to Florence on Departure day*
– Curated local experiences
– Spa experience (with optional massage add-on)
– Full retreat planning and coordination
– On-the-ground support throughout the journey
– Integrated coaching during the retreat
– Pre- and post-retreat coaching support– A small, intentionally curated group experience (limited to 6 participants)
*Note: Private transfer is for the group, with pickup at a designated place and time.
-
– Airfare to/from Italy
– Transportation outside of group transfer on arrival day
– Meals or beverages outside of those included
– Alcoholic beverages (optional curated wine package available)
– Personal expenses (laundry, shopping, etc.)
– Optional add-ons (massage, extended stay, etc.)
– Travel insurance (recommended) -
– Wine package for dinners
– Massage and spa services
– Additional night(s) in Tuscany
Travel & Logistics
-
Participants will fly into Florence (FLR).
A private group transfer will bring you from Florence to San Miniato on arrival day.
-
You will receive detailed arrival and departure guidance after registration to help coordinate flights and transfers.
-
Your luggage will be transported between accommodations each day.
You will carry only a day pack during the walk.
-
If you wish to arrive early or stay longer in Italy, we’re happy to offer recommendations and guidance.
Or, you can add-on an extra guided day to your retreat itinerary, to explore more of Tuscany and the Val D’Orcia, including villages like Montalcino, Montepulciano, and Pienza.
Investment & Payments
-
A $1,500 deposit secures your place.
Your remaining balance is due no later than June 17, 2026 (approximately 90 days prior to the start of the retreat.)
Payments may be made by MasterCard, Visa, American Express, secure ACH deposit, or by check made payable to Pellegrina Coaching LLC.
As this is the inaugural Pellegrina retreat, current pricing reflects this first offering and will increase for future journeys.
-
Your investment includes accommodations, meals, curated experiences, logistical support, and coaching throughout the journey.
-
– Airfare
– Travel insurance
– Optional wine package
– Personal spending
Policies & Requirements
-
Travel insurance is strongly recommended and should include coverage for trip cancellation, medical care, and travel delays.
-
– The $1,500 deposit is non-refundable
– Cancellations made by June 17, 2026 (90+ days prior) may transfer payments (minus deposit) to a future retreat, if space allows
– If you cancel after June 17, 2026 (90 days prior to the retreat), all fees paid will be non-refundable.– All cancellations must be submitted in writing by email.
-
Participants should be in good health and prepared for sustained daily walking.
A doctor’s approval is recommended prior to participation.
-
This retreat is designed around seasonal availability, local experiences, and the natural rhythm of the journey.
Adjustments to accommodations, activities, or routing may occasionally be necessary. Any changes will be made with care and with the intention of maintaining the overall quality of the experience.
-
A valid passport is required for travel to Italy. It is your responsibility to ensure you meet all entry requirements.
