2015 Pilgrimage to Assisi and beyond

In the Footsteps of St. Francis and St. Clare

May 26-June 4, 2015

Led by Margaret Benefiel, Ph.D., assisted by Rachel Guaraldi, M.A.


(This pilgrimage is now full and we are forming a waiting list. If you would like to be placed on the waiting list, please fill out this application form.)

The pilgrimage is based in the beautiful Umbrian town of Assisi, hometown of Francis and Clare. With its cobblestone streets, sacred shrines, and rich tradition of culture, Assisi has been a pilgrimage destination for centuries. Days will afford ample opportunity to enjoy local cuisine, sample wines, and savor the beauty of landscape, art, and culture.  From Assisi, participants will travel to other Franciscan sites in Umbria and Tuscany.

The trip will explore the life and thought of the thirteenth-century Italian saints Francis of Assisi and Clare of Assisi, and the medieval culture and context that shaped them.  Participants will stay in a convent of Franciscan sisters in the historic center of Assisi and travel to the places and shrines in the surrounding areas where these saints lived and ministered and where they have left a spiritual imprint upon the local cultures through their writings, art, architecture, and legends.

Places we'll visit and sights we'll see:

Assisi and environs:

  • San Damiano, where St. Francis received his call (later became St. Clare's convent)
  • Basilica of St. Francis with art and relics
  • Basilica of St. Clare with San Damiano cross
  • St. Francis' hermitage, Mount Subasio
  • Porziuncola (St. Francis' headquarters)
  • Cathedral of San Rufino, including baptismal font where Francis and Clare were baptized as infants

Mount LaVerna Sanctuary, Tuscany:

  • Chapel of the Stigmata
  • Basilica
  • Mountain walking


  • Basilica of Santa Croce
  • Other well-known religious and historical sites, at your leisure

Medieval and Renaissance art:

  • Giotto frescoes of the life of St. Francis
  • Della Robbia terracottas
  • Donatello sculptures
  • Cimabue frescoes

Day-by-Day Itinerary:

This 10 day, 9 night itinerary includes visits to religious sites, beautiful countryside, and magnificent Medieval and Renaissance art.

Day One: Tuesday, May 26   Beginnings and Endings

unbria italy

Our journey will begin with a walk through Assisi, located in Umbria, “the green heart of Italy.”  Treasured as the birthplace of both St. Francis and St. Clare, Assisi instills a sense of peace and meaning in the many pilgrims who travel through its wonderfully preserved history.  Flowering balconies and frescoes can be seen at nearly every turn.  As we orient ourselves to the historic town, we will become immersed in the beauty of Assisi’s cobblestone lanes, immense gates, and medieval architecture.

Our evening will end with a group dinner at the retreat center.

Day Two: Wednesday, May 27 ⁄ Masculine and Feminine

 st. francis at san damiano looking out over the valley in assisi umbria italy

On our second day, our pilgrimage will take us to Chiesa Nuova, a seventeenth-century, Renaissance-style church in Assisi.  With its high dome and frescoes, this church was built on the grounds where St. Francis was born.  Next, we will visit San Damiano, the church where St. Francis heard God’s call and where St. Clare created her religious community.

After personal reflective time, we will gather for an evening prayer service with the Poor Clares, the contemplative order of nuns founded by St. Clare.      

Day Three: Thursday, May 28 ⁄ Stripping and Adorning

santa maria maggiore

On our third day, we will focus on the life of St. Francis as depicted in Giotto’s frescoes in the Basilica of St. Francis. We will walk to the famous scene where St. Francis renounced his family inheritance, stripping off his clothes. We will also view the church of Santa Maria Maggiore with its garden, crypt, and many frescoes. 

Day Four: Friday, May 29 ⁄ Big and Small

 st. mary of the angels porziuncula  in italy

On the fourth day, we will visit Rivotorto, a stream at the foot of Mount Subasio where St. Francis and his followers lived in an abandoned hovel. We will then travel to the Porziuncula and the church of St. Mary of the Angels, headquarters of St. Francis and his brothers, and the place to which St. Clare ran away from her family to embrace her call to serve God.

Day Five: Saturday, May 30 ⁄ Contemplation and Action

symbols of the four evangelists around the rose window of cathedral of san rufino

On our fifth day, our journey will take us to the Temple of Minerva, built over two thousand years ago and later dedicated to the Virgin Mary in the 16th century.  With its vaulted ceiling, angelic statues, and altar, the impressive temple rests in the town center of Assisi.

Next, we will tour the Cathedral of San Rufino, dedicated to the patron saint of Assisi. Embellished with lions and griffins, the cathedral façade holds a rose window encircled by symbols of the four evangelists. Inside the cathedral, we will view the font where St. Francis, St. Clare, and Emperor Frederick II were each baptized.

Finally, we will see the Basilica of St. Clare.  Home to many relics, paintings, frescoes, and a crucifix, the 13th century church also contains the tomb of Saint Clare. 

Day Six: Sunday, May 31 ⁄ Solitude and Community (Day of Silence)

mount subasio

Our sixth day will bring us to the forest gorge and isolated caves of Mount Subasio.  Here St. Francis and his followers found a quiet home in the hermitage of Carceri.  Surrounded by a thicket, the hermitage provides a secluded place for prayer and meditation, and Saint Francis returned here often throughout his life.  Following in the saint’s footsteps, we will take time to enjoy silence and solitude, returning to the convent at our own pace.

Day Seven: Monday, June 1 ⁄ Life and Death

at laverna

We will travel together to La Verna, enclosed in a forest on Mounte Penna in Tuscany where we will view the Chapel of the Stigmata, built upon the sacred ground where St. Francis received the stigmata during forty days of fasting. We will also visit Santa Maria degli Angeli and Basilica Maggiore to view their art and relics. 

Day Eight: Tuesday, June 2 ⁄ Everything and Nothing

basilica of st. francis  in assisi umbria italy

The day will begin with a discussion about the Assisi Underground during World War II. We will then walk to the Assisi town museum, to the breathtaking Basilica of St. Francis, and to Hotel Subasio with its historic architecture and views of the valley. Finally, we will visit the church and abbey of San Pietro.

Day Nine: Wednesday, June 3 ⁄ The Soul’s Journey into God

santa croce 2

On the ninth day, we will travel to Florence to visit one of the world's largest and oldest Franciscan churches, the Basilica of Santa Croce. Often referred to as the Temple of Italian Glories, the basilica houses the tombs of many notable and inspirational Italians, including Michelangelo and Galileo. Like many Franciscan churches, the Basilica of Santa Croce contains narrative frescoes depicting the lives of Christ and saints. The frescoes, sculptures, and stained-glass windows were created by such Italian masters as Giotto and Donatello.  After visiting Santa Croce, pilgrims will spend the rest of the day in Florence on their own, exploring the art, architecture, and spirituality of the city.

Day Ten: Thursday, June 4 ⁄ Endings and Beginnings

sunset assisi 

We will end our pilgrimage together with a final day of contemplative practice, closing reflections, and midday meal, as we prepare to integrate the wisdom we have gained into our everyday lives.

Costs and Conditions:

Cost: $1900 per person for double room, $2200 per person for single room.  Cost includes room and breakfast and lunch daily, plus dinner on three nights, and all land travel and entrance fees during the pilgrimage.  Participants are responsible for their own travel arrangements and costs to Assisi. Trip insurance is not included, and participants are encouraged to acquire their own. Trains and buses run regularly from Rome. (See ItaliaRail for more details).

After the initial $750 nonrefundable deposit, payments are due as follows:

March 1:
Single: $725
Double: $575

April 15:
Single: $725
Double: $575


For more information on Assisi, visit: http://www.sacred-destinations.com/italy/assisi

View photos of past pilgrimages:




Please fill out the registration form.

Optional Pre-Pilgrimage Day in Rome:

Arrive in Rome on Monday, May 25th, a day before the pilgrimage begins and be met at the airport (Fiumicino). We will take the train into Rome and stay at Fraterna Domus, near St. Peter's Square. You will have the opportunity to rest, visit the Vatican, walk around Rome and have dinner together along the Tiber. On Tuesday, we will travel together to Assisi. Specific walking tours, led by Margaret and Rachel will be organized based on the interest and energy of the participants. We request that for an airport escort, you arrive by noon on Monday, May 25th. Cost of this Pre-Pilgrimage Day includes lodging, train from the airport to Rome, dinner Sunday evening and breakfast Monday morning. The cost does not include other meals, souvenirs, or train fare to Assisi.  Double Room cost is $100, Triple Room cost is $80. If you are interested in participating, please indicate your room choice on the registration form.

About Margaret Benefiel:

margaret author centralMargaret Benefiel, Ph.D., has led or co-led five previous pilgrimages to Italy.  As a Quaker and a spiritual director, she finds great inspiration from Saints Francis and Clare. Dr. Benefiel is also a consultant and retreat leader and has served in various leadership roles in Spiritual Directors International and as Chair of the Academy of Management's Management, Spirituality, and Religion Group. She is also an adjunct faculty member at Andover Newton Theological School in Boston and a visiting lecturer at All Hallows College in Dublin, Ireland. For the 2003–2004 academic year, she held the O'Donnell Chair of Spirituality at the Milltown Institute in Dublin. Dr. Benefiel is the author of Soul at Work (Seabury, 2005) and The Soul of a Leader (Crossroad, 2008), and co-editor of The Soul of Supervision (Morehouse, 2010). She has also written for The Leadership Quarterly, Management Communication Quarterly, Managerial Finance, Journal of Organizational Change Management, Organization, Personal Excellence, America, Presence, The Way, Studies in Spirituality, Radical Grace, and Faith at Work.

About Rachel Guaraldi:Rachel2

Rachel is a practitioner and scholar of peace-building, interreligious dialogue and community development. She holds a graduate degree in teaching from Towson University and a religious studies graduate degree from the Earlham School of Religion. Rachel is a member of the Religious Society of Friends (Quaker), a community that she shares with Margaret. Pairing her passions in interreligious dialogue and nonviolence with her gifts in storytelling and vocal ministry, Rachel often travels to share her experiences with others. Pilgrimage as part of life is central to her current reflections and writings. Rachel walked the Camino de Santiago in 2009, where she started cultivating a love and practice of traditional Christian contemplation into her life. Rachel is currently part of a Clinical Pastoral Education Program at Brigham & Women’s Hospital in Boston where she is training to be a chaplain. She also volunteers with Christian Peacemaker Teams on the Steering Committee and participates in the Soul of Leadership Program, a program that integrates contemplation practices with leadership skills. Rachel is thrilled to serve as program assistant and work with Margaret on this pilgrimage to Assisi and beyond. 

Frequently Asked Questions:

What time should I arrive on the first day of the pilgrimage?
The pilgrimage will begin at 4:30 PM on May 26.  You may arrive earlier to settle into your room if you would like. 

How physically active will we be?
We will be walking each day. Assisi is quite hilly, so you need to be comfortable walking up and down hills. You should be in relatively good health.

Do I need to read anything in advance?
If you would like to read something in advance, we provide a suggested reading list.  No reading is required, and no prior knowledge of the saints is required.

What should I know about train travel?
You can purchase a train ticket from Rome’s Fiumicino Airport to Assisi ahead of time through ItaliaRail, or you can buy your train ticket after arriving. Getting through immigration and customs at the airport can sometimes take an hour or more, so be sure to allow enough time to get to your train if you purchase a ticket in advance.  Either way, you must validate your train ticket at the machines on the train platform before boarding the train or you could get a hefty fine when the conductor comes through the train to collect tickets.

If you purchase your ticket online, most routes will take you to the main train station in Rome (Termini) and then out to Assisi.  If you buy your ticket at the airport, you can bypass the main train station in Rome.  From Assisi, you can take a cab ride or city bus to the convent where we will be staying.

What is the easiest way to access money while in Italy?
The best way to access cash in Italy is to use ATM's.  Travelers' checks are less convenient because they must be cashed through banks, and bank hours are irregular.

Please note: Your bank may want to know the dates you will be in Italy, so that they know it is you using your ATM card, and not someone else.

Can I use my mobile phone in Italy?
If you want to use a mobile phone while in Italy, you should check with your service provider to arrange a plan that works in Italy.

What should I wear?
Dress is casual, although pilgrims are asked to not wear shorts at sacred sites.  Sleeveless tops are also discouraged unless covered by a shawl. Bring supportive walking shoes if you would like them for our longer walks.

Average weather conditions can be found through Trip Advisor.

What should I bring?
Feel free to bring a musical instrument, art supplies, a journal, and/or anything else that nurtures your soul.  Our pilgrimage will have a contemplative pace: we will have reflective time at the convent where we are staying, time to visit sites, and individual time for you to use as you wish.

Does the convent have a washing machine and dryer?
No, the convent does not have a laundry facility. However, a laundromat is located within 500 meters of the convent.

Does the convent have hair dryers?
Yes, the convent has hair dryers.

How else can I prepare?
Please bring any medical information you would like doctors to know in case of emergency.

Pilgrims interested in learning Italian might consider using the Mango Library Edition app from Mango Languages (free for patrons at participating libraries).  Instructions can be found here: http://www.mplonline.org/mango-language-learning.html.  Contact Mango Languages or your local public library for help. 


If you have questions or comments, please contact Michelle at mabbott@executivesoul.com