Retreat Itinerary
Retreat Day 1
Friday Evening
Introduction and night prayer.
6:00pm Evening Meal
7:30pm Introduction to retreat
9:00pm Night Prayer & Silence
(until evening meal on Saturday)
Retreat Day 2
Saturday
First Rupture – Intrapsychic: this session helps us to understand our relationship with ourselves and the deeper dynamics within our interior life.
Second Rupture – Spiritual: we explore how our relationship with God can become wounded and how grace restores and renews the human heart.
8.00am Mass
8:45am Breakfast
9:30 am Talk 1 (Healing the First Rupture)
11:00am Tea / Coffee break
11:30 am Small Group Sharing (single sex groups)
12:30pm Lunch
2:00pm Talk 2 (Healing the Second Rupture)
3:00 pm Tea / Coffee break
3:30 pm Small Group Sharing (single sex groups)
4:30pm Free time (silence)
6:30pm Dinner (Silence ends)
7:30pm Holy Hour / Confessions/Night Prayer
9:00pm Social
Retreat Day 3
Sunday
Third Rupture – Interpersonal: this session examines how our relationships with others shape our daily lives.
Fourth Rupture – Habitational: this session helps us to understand our work/life balance, addressing busyness, routine and daily habits.
8:00am Mass
8:45am Breakfast
9:30am Talk 3 (Healing the Third Rupture)
11:00am Tea / Coffee break
11:30am Couple Sharing
12:30pm Lunch
1:30pm Talk 4 – (Healing the Fourth Rupture)
2:30pm Couple sharing
3:30pm Closing Prayer
6:30pm Dinner
Pilgrimage Itinerary
Pilgrimage: Arrival Day – Monday
Arrival in Italy
Pilgrims arrive in Pisa and travel to the beautiful walled city of Lucca, one of Tuscany’s most elegant and peaceful historic towns. Lucca itself has been welcoming travellers for centuries. Its wide Renaissance walls encircle a labyrinth of quiet streets, Roman remains and graceful churches that invite reflection before the road begins. In the afternoon, the group travels to San Miniato to settle in to the accommodation. In the evening, everyone gathers for an orientation meeting to introduce the Via Francigena, discuss the coming stages and set the spiritual intention for the pilgrimage.
Walking
No scheduled Walk
Focus
Arrival & Orientation
Terrain
Historic city streets
Profile
Gentle arrival day
Place of Interest
Lucca Cathedral – Duomo di San Martino houses the revered Volto Santo, an ancient wooden crucifix deeply venerated by pilgrims throughout the Middle Ages.
Terrain Summary
Town pavements, old stone streets and a gentle optional walk along Lucca’s famous walls.
Walking Profile
A restful arrival day with space to settle, pray and prepare.
Pilgrimage: Day 1 – Tuesday
San Miniato → Gambassi Terme
This stage begins one of the most scenic sections of the Via Francigena. Leaving the hilltop of San Miniato, the route descends into classic Tuscan countryside: vineyard tracks, dirt farm roads and gently rolling hills stretching toward the horizon. The terrain feels open and expansive, with wide skies and long views across the Val d’Elsa. Pilgrims pass small chapels, isolated farmhouses and quiet woodland sections that offer welcome shade during warmer months. The landscape has a timeless quality. Here, it is easy to imagine the generations of pilgrims who have walked this same route. The day ends in Gambassi Terme, a small spa town known for its thermal waters and welcoming pilgrim atmosphere.
Distance
Approx. 24 km
Walking Time
5-6 hours
Terrain
Vineyard paths, dirt roads, hills
Difficulty
Moderate
Place of Interest
Sanctuary of Santa Maria a Chianni has long offered pilgrims a place for quiet prayer and rest along the road.
Terrain Summary
Classic rolling Tuscany with broad views, sun-exposed farm tracks and some shaded woodland stretches.
Walking Profile
A flowing up-and-down stage with a steady pilgrim rhythm throughout.
Pilgrimage: Day 2 – Wednesday
Gambassi Terme → San Gimignano
After the longer walking days, this shorter stage offers a more relaxed rhythm. The path winds through quiet farmland, wooded hillsides and vineyard paths before the famous towers of San Gimignano appear on the skyline — one of the most iconic sights in Tuscany. Approaching the town is unforgettable. The medieval towers rise dramatically above the surrounding countryside, marking the final climb into one of Italy’s most remarkable historic towns. Arriving earlier in the afternoon allows time to explore the cobbled streets, artisan shops and peaceful squares.
Distance
Approx. 14 km
Walking Time
3-4 hours
Terrain
Farmland, hillside paths, final climb
Difficulty
Moderate but shorter
Place of Interest
Collegiata di Santa Maria Assunta contains extraordinary fresco cycles depicting scenes from the Old and New Testaments, created to inspire and instruct medieval pilgrims.
Terrain Summary
A shorter rural stage with open tracks, vineyard sections and a memorable approach to the hilltop town.
Walking Profile
Shorter overall, with the main effort saved for the approach into San Gimignano.
Pilgrimage: Day 3 – Thursday
San Gimignano → Monteriggioni
This is the longest walking day of the pilgrimage and often feels like the most authentic pilgrim stage. Leaving San Gimignano, the path descends into the Elsa Valley, passing vineyards, farmland and stretches of woodland. The route alternates between quiet country roads and natural trails, providing a varied and rewarding landscape. Gradually the terrain begins to rise again as pilgrims approach the extraordinary sight of Monteriggioni, a perfectly preserved medieval walled village standing on a hilltop. The circular stone walls and watchtowers appear almost exactly as they did centuries ago when pilgrims first approached this fortified refuge. Walking through its gates is a moment many pilgrims remember vividly.
Distance
Approx. 30 km
Walking Time
6-7 hours
Terrain
Valley paths, rural lanes, long rolling day
Difficulty
More demanding
Place of Interest
Monteriggioni Fortress Village remains one of the most intact fortified villages in Italy and a historic stopping point for travellers on the Via Francigena.
Terrain Summary
The longest stage: descending, traversing and rising again through mixed rural terrain, woodland and open valley sections.
Walking Profile
A full and demanding day with sustained distance and a strong finish.
Pilgrimage: Day 4 – Friday
Monteriggioni → Siena
The final stage of the pilgrimage leads through the gentle countryside surrounding Siena. The route alternates between woodland paths, gravel tracks and quiet farmland roads before gradually descending toward the historic city. Pilgrims traditionally enter Siena through Porta Camollia, the northern gate where travellers arriving from France once entered the city. Inscribed above the gate is the phrase: “Cor magis tibi Sena pandit” — “Siena opens her heart to you more than this gate.” From here, the route continues through the historic streets until the magnificent Piazza del Campo and Siena Cathedral come into view. For many pilgrims, this moment carries deep emotion; the sense of having walked a meaningful journey step by step.
Distance
Approx. 20 km
Walking Time
4-5 hours
Terrain
Woodland, gravel, city approach
Difficulty
Moderate
Place of Interest
Siena Cathedral (Duomo di Siena), dedicated to the Assumption of the Blessed Virgin Mary, is one of Italy’s most extraordinary churches. Basilica of San Domenico, where relics of Saint Catherine of Siena are preserved, offers a powerful connection to one of the Church’s great saints.
Terrain Summary
A gentler concluding stage through wooded and agricultural land before the moving urban entry into Siena.
Walking Profile
Steady walking with a meaningful final approach into the city.
Pilgrimage: Day 5 – Saturday
Departure from Siena
After completing the walking stages, the final morning allows time to enjoy Siena at a relaxed pace before taking the train to Rome.
Upon arrival in Rome, you will be transferred to your accommodation. The afternoon is yours to explore the city at your own pace, before we gather once more for a final dinner to mark the close of the retreat and pilgrimage.
Walking
Optional city stroll
Focus
Departure & Debrief
Terrain
Historic streets
Profile
Restful close
Place of Interest
Siena Cathedral and the streets around Piazza del Campo offer a final opportunity for thanksgiving before onward travel.
Terrain Summary
No scheduled walking apart from optional sightseeing in Siena.
Walking Profile
A light final morning to gather, reflect and depart.
Pilgrimage: Optional – Sunday
Optional: Sunday Morning
10:30 AM Mass at St Peter’s Basilica followed by the Angelus and the Pope’s address in St Peter’s Square at noon.
Walking
Optional city stroll
Focus
Mass & Departure
Terrain
Historic streets
Profile
Restful close
Place of Interest
St Peter’s Basilica
Terrain Summary
No scheduled walking
Walking Profile
No scheduled walking
Why this pilgrimage works so well
San Miniato to Siena offers a beautiful progression: a gentle beginning, increasingly rich landscapes, unforgettable hill towns and a final arrival that feels both moving and complete. It is long enough to feel like a true journey, yet contained enough to work wonderfully for a guided group.
For those who have already spent time on retreat, it becomes a natural next step — a way of carrying prayer into movement and discovering how the Lord meets us on the road, one faithful step at a time.
“Pilgrimage changes not only where we go, but how we walk — with greater intention, deeper gratitude and hearts more open to grace.”
Some journeys begin with a step, others with a quiet knowing.
Enquire about upcoming small-group journeys to explore whether this retreat and pilgrimage is right for you.