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A pilgrimage is a sacred journey taken to encounter God

“To travel is as a tourist is acquisitive —
what photos and stuff can I bring home?
[But] to travel as a pilgrim is receptive —
what does God want to give me
and how can I be receptive to that?”
— Susan Skillen

Join us for a life-changing ten days in Subiaco, Assisi, and Rome (optional extension of an additional three days), Italy, as we follow in the footsteps of Saints Benedict and Scholastica, and Saints Francis and Clare. Benedict (6th C) became the founder of the Benedictine monastic order, which influenced many other orders through its stability, education and vision of a Christian future amidst a chaotic and crumbling Roman empire. Francis (13th C) founded a new traveling order of the Lesser Brothers/Franciscan Friars Minor, and brought hope to a struggling medieval Church. Their visions of inner transformation through spiritual disciplines and simple adherence to the Gospel revolutionized the Church.
Sacro Speco (the shrine of Benedict’s Sacred Cave) in Subiaco

Sacro Speco in Subiaco
(the shrine of Benedict’s sacred cave)

The first day, we leave Rome to visit sacred sites in Subiaco for three days, where Benedict lived in a cave, and Montecassino, location of his first abbey. This is followed by another three days in Assisi, where we learn about Francis and Clare, his first female follower and founder of the order of the Poor Clares. Our time in Assisi concludes with a three-day quiet guided prayer retreat.

Pilgrims can add an optional 3-day/3-night extension in Rome. A highlight is the Vatican Scavi tour of the excavations beneath St. Peter’s Basilica, which reveal the ancient tomb of the Apostle Peter. Besides visiting other sites in the Eternal City, travelers have one free day to explore on their own.

Sacro Speco (the shrine of Benedict’s Sacred Cave) in Subiaco

The Basilica of San Francesco in Assisi

Pilgrimage Costs (per person)
$2,600.00 (double occupancy) —10 days
$3,000.00 (single occupancy) — 10 days
$   600.00 (double occupancy) — 3-day optional Rome extension
$   700.00 (single occupancy)  — 3-day optional Rome extension
Pilgrimage costs include all lodging, ground transportation, three meals a day (except first/last day), entrance fees & tips, but not airfare

Sacro Speco (the shrine of Benedict’s Sacred Cave) in Subiaco

The Abbey of Montecassino,
site of the first Benedictine house

Days 1-3: Benedict & Scholastica

Sunday, June 18 — Tuesday, June 20

We leave Rome and travel 1.5 hours by bus to Subiaco, site of Sacro Speco. As we settle into our retreat center, we learn about Benedict and his sister, Scholastica. On Day 3, we travel to the Abbey of Montecassino, where Benedict founded his Benedictine Order in AD 529. In keeping with Benedictine tradition, we keep the rhythms of morning, noonday and evening prayer throughout our pilgrimage.

Days 4-6: Francis & Clare

Wednesday, June 21 — Friday, June 23

Departing Subiaco on Day 4 for Assisi, we lunch in Norcia, the birthplace of Benedict and Scholastica. After settling in at Assisi, we spend the next days visiting the churches of San Rufino, San Damiano (where Jesus spoke to Francis), Porziuncola, and the basilicas of San Francesco and Santa Chiara.

Sacro Speco (the shrine of Benedict’s Sacred Cave) in Subiaco

Basilica of Santa Chiara (Saint Clare) in Assisi

Sacro Speco (the shrine of Benedict’s Sacred Cave) in Subiaco

L’Eremo delle Carceri
(Franciscan hermitage complex)

Days 7-9: Guided Prayer Retreat

Saturday, June 24 — Monday, June 26

Day 7 starts our quiet guided prayer retreat, which begins with a hike (or taxi-ride) to l’Eremo delle Carceri (a hermitage complex 2,600 feet high on Mount Subasio) where Francis and his brothers would pray. The evening of Day 9 concludes our pilgrimage with a time of celebration.

Days 10-12: Depart or
Optional Rome Extension

Tuesday, June 27 — Thursday, June 29

Early in the morning on Tuesday, June 27, we depart Assisi (with carryout breakfasts) for the 2.5-hour trip to the FCO airport in Rome. Since we arrive by 10:00 AM, departing pilgrims should schedule their flights from FCO for after 1:00 PM.

Those opting for the Rome Extension tour have three days in the Eternal City: one day featuring the Scavi excavation tour, one for other sites in Rome, and one free day to explore on their own.

Sherpa will arrange airport transportation for departure flights on Friday, June 30.

Sacro Speco (the shrine of Benedict’s Sacred Cave) in Subiaco

St. Peter’s Basilica, Vatican City

Dates for the Pilgrimage and the Optional Rome Extension

Pilgrimage: Sunday, June 18 — Tuesday, June 27, 2023  (Please arrive at Rome’s FCO airport by noon on Sunday, June 18, and please book your departing flights for after 1 PM on Tuesday June 27)

Optional Rome Extension: Tuesday, June 27 — Thursday, June 30, 2023  (Please book your departing flights for after 1 PM on Friday, June 30)

Program or Academic Credit Information

Sherpa Program Credit 

If you are enrolled in the Sherpa Certificate in Spiritual Direction Training Program and want to count this trip as your Sherpa Capstone (spiritual immersion experience on a pilgrimage and prayer retreat), please email your confirmation of that desire to the program director ( to specify your forays and work out the details.

Optional Academic Credit

The Assemblies of God Theological Seminary at Evangel University, has offered academic credit for these pilgrimage on the bachelors, masters, and doctoral levels based on approved syllabi with additional pre-trip reading and research, on-trip journaling and mini-presentation(s), and a post-trip writing assignment plus the respective tuition payment to the educational institution.

If you are interested in pursuing academic credit, please review the sample syllabus (coming soon), check with your academic institution for details and approval, and then email Dr. Gill ( to work out the details.

Optional Pre-Reading Short List (coming soon)

Benedict & Scholastica
Francis & Clare
Scavi Tour

Pilgrimage Leaders

Debbie & Jan Gill are spiritual adventurers. Ever since their giant year-long sabbatical and pilgrimage in 2014-2015 covering twelve countries, they have been leading annual pilgrimages and prayer retreats for others seeking to go deeper in Christ. Jan is an architect, sailboat racer, and contemplative Christian specializing in ancient and Orthodox spirituality. Debbie is a seminary professor at the Assemblies of God Theological Seminary/Evangel University, an ordained Assemblies of God minister, and the founder/director of Sherpa: Guidance for the Spiritual Climb, a spiritual formation and spiritual direction ministry. Together, they love journeying deeper into the presence of Jesus and the power of the Holy Spirit.

Bethany Givens Blankespoor serves as a spiritual formation specialist for the Mid-Atlantic Region of InterVarsity. She lives in Washington, DC with her husband, daughter and two cats named Francis and Chiara. In her sixteen years serving with InterVarsity, she has worked with students on campuses at Georgetown and George Washington Universities and with InterVarsity’s National Study Abroad Ministry, overseeing European retreat and pilgrimage programs for students studying abroad. Bethany fell in love with the spiritual practice of pilgrimage and the stories of Clare and Francis in 2016 when she and her husband went on their first pilgrimage together to Assisi. Since then, she has led multiple pilgrimages to Italy, Ireland, and France.

Registration & Payment Information

Registration is now open, and requires a $100.00 deposit (refundable until February 15, 2023).

First 50% of the remaining balance (less deposit) is due March 15, 2023.

Final 50% of the remaining balance (less deposit) is due May 15, 2023.

Pilgrimage costs include all lodging at “holy houses” (retreat houses), ground transportation, three meals a day (except for the first/last days), entrance fees, tips, retreat leaders and speakers, and study and reflection materials.

Not included: airfare, souvenirs, or extra snacks/drinks. You are responsible for making your own flight arrangements to and from Rome’s Fiumicino (FCO) airport. 

Payment Information (any of the options below)
  1. Use your bank’s app to access Zelle; send payments to
  2. Use ApplePay; send payments to (417) 379-5297
  3. By check addressed to Sherpa; mail the check to 904 Coffee Berry Ct., Griffin, GA 30223

Please specify in a memo line if the payment is the “Pilgrimage deposit,” “Pilgrimage first 50%,” or “final Pilgrimage payment.”

Ground transportation is provided by Sherpa from the Rome airport on the first day, during the entire pilgrimage, and back to Rome (FCO) again.

Limited space is available. As several have pre-registered, quickly register to save your space.

Mobility Information

Towns in Umbria are small, hilly, have cobblestone streets and few elevators. This pilgrimage involves some walking up and down steps and hills, so bring appropriate and comfortable shoes. You carry your own bags in monasteries and retreat houses, so plan to pack light.

Insurance Information 

Check with your insurance provider on their international benefits (for example, do you have medical coverage overseas?).

When you book your flights, consider adding international travel insurance (Allianz, for example, offers international medical coverage, trip cancellation, flight delay, and lost baggage coverage).

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