Pilgrimage Retreat Details
April 8–17, 2027
Detailed Itinerary
9 nights in Tuscany | Limited to 8 women
Day 1 — Arrival in Tuscany
We arrive in Florence, and a private car takes us straight into the Tuscan countryside. Rolling hills, cypress trees, and small hilltop villages begin to set the tone for what's ahead.
We settle into a villa near San Miniato, our home for the first two nights. After time to rest in your private room, we'll gather for a short welcome before our first dinner together.
Day 2 — San Miniato
A day to settle before the walking begins.
After the travel, we give our bodies a chance to recover. The mind begins to quiet. Through guided conversation and intention setting, the group eases into a different kind of time together, and the connection that will carry us through the walk begins here.
There's time to connect with others, or to do nothing and simply take in the view.
Day 3 — Walk 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. We arrive at Tenuta Sant'Ilario, a peaceful hilltop estate just outside the village, with sweeping views across the Tuscan valley to the snow-capped Appennini.
Dinner is shared on-site.
Day 4 — Walk Gambassi Terme to San Gimignano
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 — Walk San Gimignano to Colle di Val d’Elsa
A steady walking day brings us to Colle di Val d’Elsa.
Day 6 — Walk 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 — Walk 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.
Day 8 — Walk Siena to Buonconvento
On our sixth and final walking day, we continue south along the Via Francigena, moving deeper into the Tuscan landscape.
We arrive in Buonconvento, in the Crete Senesi region south of Siena, a landscape known for its expansive views, winding roads, and quiet beauty. We'll spend our last two nights here at a family-run agriturismo.
Day 9 — Rest in Buonconvento
A full day at the end of our journey, with time to rest our bodies and reflect on what we've walked. We look back at the insights that came up along the way and begin integrating the experience, individually and together.
Day 10 — Departure
A group transfer returns us to Florence at a set time that morning. From there, you can continue home or spend more time in Italy on your own.
After days of walking, conversation, and reflection, this is where the pilgrimage comes to a close.
Want to learn more? Schedule a chat.
The Rhythm of Each Day
Each day has a few natural points of connection and reflection.
Morning— Setting an Intention
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 short, but they give the day a clear starting point.
On the Trail — Conversation Along the Way
Much of the walk is open time—walking alongside others, or alone with your own thoughts.
Some days that turns into a long conversation on the path. Sometimes it's a question, or a moment of insight, that shows up in the walking itself. I'm walking with you, and when something deserves a closer look, there's room to explore it together.
Because you are in your life—not talking about it from a distance—what you notice tends to land more deeply and more honestly.
Evening— Reflection
At the end of each day, we gather for a short reflection. You may share a moment that stayed with you—something you noticed, a question that surfaced, a shift in perspective—or simply listen. These conversations are simple, grounded, and often unexpectedly meaningful.
Investment
April 8–17, 2027
9 Nights
Limited to 8 women
$6,888 per person
(single occupancy accommodations)
A $1,500 deposit secures your place, with the remaining balance due by March 1, 2027.
This includes accommodations (private rooms), daily luggage transfer, all breakfasts and dinners (and most lunches), curated experiences, daily guided reflection, and preparation support before you go.
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.
How to Apply
We start with a conversation.
This is a small group — eight 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 & FAQs
The Journey
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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.
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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.
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We will walk for 6 consecutive days and daily distances range from approximately 9 to 18 miles (14–29 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.
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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.
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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.
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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.
Accommodations, Food & Wine
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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.
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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.
Preparation & Support
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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.
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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 -
A few weeks before the retreat, we'll gather once by video call. It's informal and optional—a chance to:
meet the other women in the group – ask packing and preparation questions
review logistics
share a little about what's drawing you to this walk
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In the months leading up to the retreat, you'll have access to support for training, preparation, and logistics questions as you get ready for the journey.
If you'd like more one-on-one time to prepare, individual coaching is available separately.
Experiences Along the Way
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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 SienaThese experiences are intentionally spaced throughout the retreat, allowing them to enhance—not interrupt—the rhythm of the walk.
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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 -
Reflection is part of the rhythm of each day. Mornings begin with a short intention over breakfast, evenings close with a group reflection, and in between there's room for conversation on the trail—including one-on-one time with me when it's helpful. Insights can be explored while you're still in the experience, not just after the fact.
What’s Included & Not Included
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– 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
– Complete retreat planning and coordination
– On-the-ground support throughout the journey
– Daily morning and evening reflections, with one-on-one conversation along the trail
– Training plan, packing list, and a pre-retreat group call– A small, intentionally curated group experience (limited to 8 participants)
*Note: Private transfer is for the group, with pickup at a designated place and time.
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– Airfare to/from Italy
– Transportation outside of group transfer on arrival and departure days
– Meals or beverages outside of those included
– Alcoholic beverages (optional curated wine package available)
– Personal expenses (laundry, shopping, etc.)
– Optional add-ons (massage, services, etc.)
– Travel insurance (REQUIRED) -
– Wine package for dinners
– Massage services
Travel & Logistics
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Participants will fly into Florence (FLR).
A private group transfer will bring you from Florence to San Miniato on arrival day.
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You will receive detailed arrival and departure guidance after registration to help coordinate flights and transfers.
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Your luggage will be transported between accommodations each day.
You will carry only a day pack during the walk.
Investment & Payments
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A $1,500 deposit secures your place.
Your remaining balance is due no later than March 1, 2027.
Payments may be made by MasterCard, Visa, American Express, secure ACH deposit, or by check made payable to Pellegrina Coaching LLC.
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Everything on this retreat is handled for you, so all you need to do is arrive, be present, and walk. Your investment includes accommodations, breakfasts, dinners, and most lunches, curated experiences, logistical support, and guidance throughout the journey.
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– Airfare
– Travel insurance
– Optional wine package
– Personal spending
Policies & Requirements
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Travel insurance is required and should include coverage for trip cancellation, medical care, and travel delays.
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– The $1,500 deposit is non-refundable
– Cancellations made by February 7, 2027 (60+ days prior) may transfer payments (minus deposit) to a future retreat, if space allows
– If you cancel after February 7, 2027, all fees paid will be non-refundable.– All cancellations must be submitted in writing by email.
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Participants should be in good health and prepared for sustained daily walking.
A doctor’s approval is recommended prior to participation.
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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.
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A valid passport is required for travel to Italy. It is your responsibility to ensure you meet all entry requirements.
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.