"For most of us our greatest contribution is yet to come." 
~ Chris Bruno

Dates: ​May 21-31, 2026  (Men Only)

Register Today (February 1st Deadline)

What's the Focus

The focus of this journey, following the life of Saint Francis of Assisi, is to use pilgrimage as a way for men to reflect on the path they have taken thus far and consider the journey ahead as they traverse the middle stage of life. There comes a point in almost every man's journey, usually after the age of 35, where the driving focus of a man’s life shifts from a desire to be successful towards a longing for significance. 

The strategies that gained men success in their personal lives, families, vocation, churches, and community in the first half of life may no longer work or they may not have the same allure they once had. Whatever the impetus, men in the middle stages of life are being invited on a deeper journey, a journey from success to significance. 
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St. Francis of Assisi was a man born into success, with all the trappings of women, wealth, and power. When this form of life failed to produce the results he was looking for, he found himself fascinated by another way, the way of significance. This way emblazoned his identity as “il Poverello,” or “the little poor man” in the eyes of the world, but it elevated him to become one of the most written about Christian saints of all time. 

Walking 135 kilometers along the paths and among the towns that St. Francis himself walked, we will explore themes of ego, surrender, humility, and suffering as pathways by which men might be reborn, made new, and elevated to a place of significance in God’s kingdom. 

This journey is for any man looking to slow down and consider God’s invitation in this unique season of life. By way of eight stages, we will guide you through the essential way markers you need to navigate "the middle passage" and live a life of significance in the second half of life. 

Cost: $2,750 per person 

​This pilgrimage is designed for MEN ONLY aged 35+
Price is based on 6 participant minimum

Itinerary Highlights

Itinerary Details

Day 1
Arrive in Florence and explore this cultural gem where Michaelangelo's David, the famous Duomo Cathedral, and countless other cultural artifacts rest. Head to La Verna that night. 

Day 2
La Verna to Pieve Santo Stefano - Set your pilgrimage intention, pick up a stone of remembrance, and walk through an enchanted forest as we take off together to begin the first stage (10 miles).

Day 3
Pieve Santo Stefano to La Montagna - Travel through rugged terrain on one of the toughest stages on the trip and enjoy a home-cooked Italian meal in the mountains (13 miles). 

Day 4
La Montagna to Fighille - Travel 3,000 ft down into the Upper Tiber Valley through the walled city of Sansepolcro and into one of the many small towns along the route (13.5 miles).

Day 5
Fighille to Citta di Castello  - Cross from Tuscany into Umbria, through the charming medieval hill town of Citerna and spend the night in the ancient fortified city of Citta di Castello  (15 miles).

Day 6
Citta di Castello to Pietralunga - Make your way through the Umbrian countryside to the center of the Anti-Fascist movement during the 2nd World War (14 miles).

Day 7
Pietralunga to Gubbio - Experience stunning views as you pass through vineyards on your way to our favorite city on the route  (14 miles)

Day 8
Rest Day in Gubbio - Take a day to explore, reflect and discover the meaning of your pilgrimage thus far. 
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Day 9
Valfabbrica to Assisi - Walk the final stage of the pilgrimage stopping to set down your stone before arriving in Assisi the home town of Saint Francis. Debrief our journey over good food and wine at a local winery (8.5 miles).

Day 10
Depart and/or optional personal travel to other locations. 
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What's Included

• Four pre-trip & two post-trip meetings via Zoom 
• Transportation from Florence to La Verna
• 9 Nights Accommodation (B&B's, hotels & monasteries), standard double occupancy
• Two Dedicated Pilgrim Guides (see below for guide introductions)
• All Breakfasts and Dinners
• Custom Guidebook
• Official Pilgrim Stamp Book
• Umbrian Culinary Experience & Winery Tour 
• Spiritual Direction or Mid-Life Coaching Per Request

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What's not Included

• Airfare
• Airport Transfer on day of arrival to Florence City Center
• Any Travel Plans Pre or Post Trip
• Passport, Visa, or Luggage Fees
• Backpacking/Hiking Gear
• Any Personal Purchases
• Any Meals not Indicated on Itinerary, as well as beverages at meals
• Travel Protection/Insurance (Recommended)
• Anything else not explicitly mentioned as included​​

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Your Guides

Shaun Grindle (right)

​After living in six major cities on two continents I am still learning to walk at the pace of Jesus. With my beloved wife, Karisa, we have four beautiful children who keep me on my feet. I enjoy reading, crossfit, and imparting the value of drinking hot water on unsuspecting acquaintances. ​

Stephen Grindle (left)

After hitting a midlife awakening in the form of an unwanted divorce, following Jesus in the way of Francis has become a means by which I'm learning to heal, forgive, and reinvent myself.  I've found Francis' way of life to be the most integrative approach to personal and social transformation. As such, I am building my "new" life around a spirituality of surrender, wakefulness, and justice. In my free time, I love to make wine, play volleyball, and wrestle with my four boys.