"I have come that you may have life, an overflowing, abundant life."
~ Jesus
~ Jesus
Sept 12-23, 2026 (FULL)
The mist of the morning floats over the rolling hills.
Sunlight floods the muted landscape giving shape to ancient villas.
Cypress trees awaken like sleeping centurions guarding the gates to Eden.
As you scan the rows of trellised vines on the horizon,
You breathe in the day with expectation, and begin to walk the path.
Like so many before, longing for an encounter with the Divine.
You are walking the Via Francigena and this is The Way of the Vine.
Sunlight floods the muted landscape giving shape to ancient villas.
Cypress trees awaken like sleeping centurions guarding the gates to Eden.
As you scan the rows of trellised vines on the horizon,
You breathe in the day with expectation, and begin to walk the path.
Like so many before, longing for an encounter with the Divine.
You are walking the Via Francigena and this is The Way of the Vine.
What's the Focus
The focus of this pilgrimage is on the abundant life as you walk 92 miles over 8 days from Lucca to San Quirico d'Orcia, a journey from Chianti to Brunello, some of the most well known vineyards of Tuscany. The theme of vineyards in sacred texts are often used to symbolize prosperity, or God’s blessing and abundance. Vineyards are also a place of joy and gladness, where celebration, singing and cheer take place. You might say vineyards represent a place of shalom or peace, where the state of our souls can be tended to by the vinedresser.
Through daily walks we'll be asking:
1) how do vineyards relate to the human experience?
2) what is the abundant life and where do we find it?
The focus of this pilgrimage is on the abundant life as you walk 92 miles over 8 days from Lucca to San Quirico d'Orcia, a journey from Chianti to Brunello, some of the most well known vineyards of Tuscany. The theme of vineyards in sacred texts are often used to symbolize prosperity, or God’s blessing and abundance. Vineyards are also a place of joy and gladness, where celebration, singing and cheer take place. You might say vineyards represent a place of shalom or peace, where the state of our souls can be tended to by the vinedresser.
Through daily walks we'll be asking:
1) how do vineyards relate to the human experience?
2) what is the abundant life and where do we find it?
Highlights
Cost: $2,650 per person
(based on 8 participant minimum)
(based on 8 participant minimum)
What's Included
- 11 nights accommodation (combination of hotels, B&B and pilgrim monasteries), standard double occupancy.
- All baggage transport for those not wanting to carry a backpack
- Dedicated pilgrim guide & on call van support
- Bicycle Tour of Lucca
- Entrance to Siena Cathedral
- Picnic Lunch in Vineyard
- Custom Via Francigena guidebook
- ALL dinners and some breakfasts
- Pre-travel prep and themed content
What's not Included
- Airfare
- Airport transfers on day of arrival (first night will be in Lucca which is a quick train ride from Pisa)
- Transfer from Ponte d'Arbia on departure day (trains available to get to airports)
- Recovery day activities (i.e. thermal spas, massages)
- Single room supplement (optional add-on of $500)
- Passport, visa, or luggage fees
- Any personal purchases
- Some breakfasts & all lunches
- Recommended travel protection/insurance
- Anything else not explicitly mentioned as included
Itinerary (subject to change)
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Saturday, Sept 12: Arrival Day
Theme: Orientation After arriving into Lucca, you'll be welcomed and hosted in a 17th century villa just outside its magnificent city walls, one of the few examples of walls that have remained completely intact. Enter into the charmed history of what used to be a Catholic convent, explore the olive gardens and meet your fellow pilgrims. |
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Sunday, Sept 13: Day in Lucca
Theme: Vision of Vineyards Lucca captivates visitors with its picturesque alleys, squares and characteristic churches. You'll also witness, the Luminara di Santa Croce, an annual candlelit procession celebrating the Volto Santo (Holy Face). Thousands of candles light up the city's historic center, creating a magical atmosphere, followed by a procession from San Frediano to San Martino Cathedral and ending with fireworks. |
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Monday, Sept 14: Lucca to San Miniato (6 miles)
Theme: The Soil You will ease into the day with a short walk on a variant of the Via Francigena through a forested nature reserve to Sant Andrea di Compito, followed by an hour van transfer to San Miniato, whose enormous tower can be seen for many miles as a beacon to pilgrims on the Via Francigena. San Miniato is also home to Napoleon Bonaparte’s family and features his family's chapel. |
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Tuesday, Sept 15: San Miniato to Gambassi Terme (15 miles)
Theme: The Trellis Now the vast rolling hills open up and this very picturesque day will carry you through beautiful farmland with constant, sweeping vistas of the Tuscan countryside. Arrive at Ostello Sigerico, one of the original churches Archbishop Segeric stayed at on his way to Rome. |
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Wednesday, Sept 16: Gambassi Terme to San Gimignano (9 miles)
Theme: The Branch San Gimignano, a UNESCO world heritage site, is the jewel of medieval architecture, with dozens of towers where prosperous families stored their treasures. Enjoy strolling the streets at night, eating gelato and sipping the famous Vernaccia white wine. |
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Thursday, Sept 17: San Gimignano to Colle di Val d’Elsa (9 miles)
Theme: The Water This smaller, less crowded medieval city accounts for 95% of Italian crystal glass production. It is also home to Elsa River Park, a stunning 4km walk developed and commissioned during the 17th century by the Grand Duke of Tuscany Ferdinando I De' Medici. |
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Friday, Sept 18: Colle di Val d’Elsa to Monteriggioni (9 miles)
Theme: The Vinedresser Monteriggioni is a fully walled medieval village atop a rounded mountain and presents itself as if time had never passed. Famous for its historic castle and towers overlooking the enchanting landscape, this Tuscan outpost was built by the Sienese to guard against their Florentine rivals. You can walk along it's walls as the sun sets. |
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Saturday, Sept 19: Monteriggioni to Siena (12 miles)
Theme: The Vine Home to the patron Saint of Italy, Catherine, there are few words worthy to describe Siena. Inside its medieval walls there are world-renowned treasures of medieval and Renaissance art, capped off by a stunningly beautiful cathedral at its heart. There's no better way to enjoy the city than through la passeggiata, a cultural,, social tradition involving a slow, leisurely evening walk around piazza del campo. |
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Sunday, Sept 20: Siena to Ponte d'Arbia (16 miles)
Theme: The Fruit After leaving behind the Siena skyline, immerse in the undulating and silent landscapes of Val d’Arbia. The journey continues on uninterrupted gravel roads, among cultivated fields, low hills and views that open up to the distant profile of Mount Amiata. |
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Monday, Sept 21: Ponte d'Arbia to San Quirico d'Orcia (16 miles)
Theme: The Harvest Among landscapes of rare beauty, this stage invites you to discover fortified villages, legendary vineyards and authentic art treasures. The path winds gently through cultivated hills and memories of peasant life, touching places of spirituality and culture. An engaging itinerary that culminates in the Renaissance grace of San Quirico d’Orcia. |
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Tuesday, Sept 22: Day in San Quirico d'Orcia
Theme: Rest & Celebration Unwind at your leisure by the pool, take in the views and enjoy the spas or get a massage. You'll have time to reflect on your pilgrimage from Chianti to Brunello and celebrate the experience with your fellow travelers. Wednesday, Sept 23: Departure Day to home or further travels |
Note: This can be a demanding pace of walking with varied levels of elevation gains. However, the beauty of the landscape and the richness of the food have a remarkable way of pushing you through the days. Even so, the following are suggestions for preparation.
• Healthy feet, knees and hips essential (trekking poles are helpful)
• Pre-training working up to 12 miles with hills encouraged (training schedule to be provided)
• Flexible and adventurous spirits expected (not recommended for comfort seekers)
• Healthy feet, knees and hips essential (trekking poles are helpful)
• Pre-training working up to 12 miles with hills encouraged (training schedule to be provided)
• Flexible and adventurous spirits expected (not recommended for comfort seekers)
Happy People
T E S T I M O N I A L S
This pilgrimage was a set-apart “timeout” clarifying personal direction, with adequate pace and space to allow for unhurried presence.
~Lance, 2025 The pilgrim culture and mindset offers one of the best opportunities I’ve experienced for connecting with people from all over the world… people who are consistently open and responsive, eager to forge new relationships. ~ Kirk, 2025 |
This journey has given me a profound understanding of how God tends to the state of my soul. There were so many moments where I felt seen, cared for, encouraged, and surprised. Please don't stop doing these trips!
~Melany, 2024 |
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Your Guide
Jon Eastwood
I've been involved in leading pilgrimages for the past decade in Ireland, Spain and Italy. It's hard to put into words the beauty of the Tuscan landscape and the richness of the Italian cuisine and culture. I enjoy setting the table for others to have a transformative experience.
