
Pilgrimage to Rome and Assisi
Chesterton Academy of the Holy Family
June 1 – 21, 2021 / $3100.00
This incredible journey will immerse the students of Chesterton Academy in the greatest moments and monuments of Roman and Christian civilization. Prepare to explore the ancient world’s most magnificent city – Rome – and witness how it became even more magnificent as it was transformed by Christianity. This trip features one week in Rome and a three-day excursion to Assisi and Orvieto.
This trip is open to Chesterton Academy of the Holy Family students and chaperones. Space is limited.
Trip Highlights
On this trip we will venture in the footsteps of the greatest saints and martyrs of our Catholic heritage. We will experience the history and magnificence of Rome firsthand, exploring the greatest sites found anywhere in the world. Most importantly we will celebrate Mass every day, reorienting and reinvigorating our lives in, through and towards Christ.

Rome
Every morning we will depart our Vatican guesthouse and set out into Rome. We will explore Rome’s greatest sites, from the tunnels of crypts and catacombs to the many ancient amphitheaters and early Christian churches.

Assisi
The trip concludes in Assisi, where we will spend two days touring the medieval city. Here the students will have the unique opportunity to get to know one of history’s greatest saints and adventurers, St. Francis.

Orvieto
On the way to Assisi we will stop in the beautiful city of Orvieto, home to one of Italy’s finest Gothic cathedrals, the Duomo of Orvieto, which serves as a solemn reliquary for the Eucharistic Miracle of Bolsena!

The Vatican
Our hotel in Rome is located just next to the Vatican – we will walk through St. Peter’s Square nearly every morning. We’ll also have the chance to see the Pope, attend Mass in St Peter’s Basilica and climb to the top of Michelangelo’s dome!
The Itinerary
From Rome to Assisi!

June 1 - 8
Rome
Rome is the Eternal City. There is no place more beautiful and more important in the history of the world than Rome. As Catholic Christians, Rome’s eternal purpose of civilizing and saving the world through the work of Christ’s Church.
This trip features one full week in Rome. During this week we will explore the history and places of Rome’s incredible three-thousand year history, highlighting the artistic and architectural treasures along the way. The itinerary includes a Papal Audience, the Colosseum and Roman Forum, the Catacombs, the Four Major Basilicas, the Best Baroque Churches and Monuments of Rome, the Jesuit Churches, Rome’s Best Museums (the Vatican Museums, the Borghese Gallery and the Capitoline Museums) and so much more.

June 9 - 11
Assisi
Known as the Seraphic City for its angelic beauty, the students will explore the timeless charm and beauty of Assisi for two days. We’ll go back in time to the 13th century, when St. Francis and St. Claire gave up their lives to follow Christ and proclaim the truth and beauty of the Faith. We’ll witness the Gothic masterpieces of Giotto and Cimabue, the great precursors of the Renaissance, and we’ll glimpse the actual beauty of a the medieval age which has so often been misrepresented as dark and unenlightened.
Many do not know the true story of St. Francis. In reality, St. Francis experienced terrible despair before his great conversion – and only recovered by clinging completely to God. His story is an incredible one, and his deeds following his mid-life conversion are absolutely epic. We’re going to relive his story – from his decadent youth to his pursuit of poverty, and from his hermitage in the mountains to his crusade to Egypt. Throughout our time in Assisi, St Francis will become a friend, a mentor, and a model for the students.

June 9
Orvieto
On the way to Assisi we will stop in the beautiful city of Orvieto, home to one of Italy’s finest Gothic cathedrals, the Duomo of Orvieto, which serves as a solemn reliquary for the Eucharistic Miracle of Bolsena, the first Church-approved Eucharistic miracle and the impetus behind the institution of the Feast of Corpus Christi!
TRIP DETAILS
Pricing & Registration
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Basic Instructions
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Start Fundraising and Putting Funds Aside
ProRome provides a fundraising guide that can be used to help raise funds for your trip. Lots of our students use this guide to make their trip possible!
Get Your Passports Ready
Apply as soon as possible. NB - Passports that expire within six months of the travel dates are NOT VALID to enter Europe.
Frequently Asked Questions
Trip Patron
St. Joseph – the foster father of Jesus Christ – is the greatest of saints. As our trip patron, we will pray to St. Joseph before and during the trip, asking this incredible man, the protector of the child Jesus, to protect us on our pilgrimage!
Meet the Team

Mrs. Julie Bowles
Mrs. Bowles served as the Executive Director of Chesterton Academy from 2015 – 2020. As the Rome pilgrimage planner and leader, she helps facilitate one of the most incredible aspects of the Chesterton experience – a pilgrimage to Rome and Assisi!
Mr. Joe Long
Joe is the tour planner and tour director. As the founder and director of ProRome, Joe has been leading trips through Europe for six years. He holds an MA in Church History and speaks fluent Italian. He looks forward to sharing the greatest places in the world with you!

Fr. Ryan Adorjan
Fr. Ryan Adorjan is our trip chaplain! The chaplain of Chesterton Academy, he is also the parochial vicar of the Cathedral of Saint Raymond Nonnatus and Sacred Heart parish. He looks forward to celebrating Mass and leading us spiritually on this pilgrimage!

ProRome Office
ProRome is a full-service tour operator and travel agency located in Charlottesville, VA. If you need anything at all – travel insurance, flight add-ons, special requests, payment extensions – do not be afraid to reach out. Someone in the office will be here to help!
Testimonials
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Travel Insurance
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Most of our clients who purchase travel insurance will never have to file a claim. This is a very good thing. If you do have to visit a hospital over in Europe, however, it is good to know that you have the world’s largest and best travel insurance provider at your back. They’ll get you in and taken care of quickly.
On another note, the majority of those who cancel their trip with ProRome do so because of an illness or death in their family prior to the trip. This is covered in most of our plans. If nothing else, this is a very good reason to purchase a plan today.