Join Chesterton Academy Alumni & Friends
A Jubilee Pilgrimage to Italy
July 18 – 27, 2025
$2690 per person, Land Only
This pilgrimage features five nights in Rome and three nights in Assisi, with day trips to Orvieto and La Verna included. Daily Mass – the cornerstone of each day – will be complemented by a touring program that will immerse the pilgrims in the incredible history, heritage and relics of our Catholic Faith. Highlights include an Audience with the Holy Father in Saint Peter’s Square, the Papal Basilicas of Rome, the Catacombs, the Colosseum and the Basilicas of Saint Francis and Saint Clare in Assisi.
Centrally-located accommodations will be arranged. A ProRome tour manager will accompany the group throughout the course of the pilgrimage, and private bus transportation, Catholic tour guides, all tours, tickets and gratuities, and daily breakfast and daily dinner are included in the price. One daily meal (either lunch or dinner) is the only item not included in the price.
This pilgrimage is open to alumni and friends (over 21 years old) who have graduated from high school at least one year prior to the trip. Currently, graduates from the years 2012 to 2024 are eligible to register.
Land Only: $2690 per person*
*Group airfare will NOT be booked for this trip. Individuals will book their own airfare. All pilgrims will be expected to arrive at Rome FCO by 11am on July 19th and depart Rome FCO after 11am July 27. All pilgrims will be notified and given the go-ahead to book their airfare once the minimum number of registrants needed is met.
Please note that this brochure is just a sampling and the final itinerary with some special activities will be released once the pilgrimage has reached the minimum of 25 people.
Trip Highlights

Rome
This pilgrimage features six full days in the Eternal City. We will explore Rome’s greatest sites, from the tunnels of crypts and catacombs to the many ancient amphitheaters and early Christian saints and churches.

Vatican City
We then will enter more deeply into the history and beauty of our Catholic Faith. Here in the Vatican City, we will experience the heart of the Church, the place of Saint Peter’s martyrdom and the seat of the Vicar of Christ, the Pope!

Orvieto & Assisi
Our pilgrimage continues with a visit to Assisi, stopping in along the way to venerate the Eucharistic Miracle of Orvieto. We will explore this incredible medieval city, following in the footsteps of the great Sts. Francis and Clare.

La Verna
We’ll conclude our pilgrimage with a day trip the Franciscan Sanctuary of La Verna. It is here in this monastery that Saint Francis received the stigmata from Our Lord. We’ll then return to Assisi for our last night in Italy.
IMPORTANT ACTION ITEMS
Planning Checklist
Registration
In order to register, click "Register Now" on the top of this webpage and follow the prompts on the form.
Passports - Upload or Apply Today
After registering we will send you a link to upload your passport. If you do not have a valid passport you must apply ASAP. It can take up to three months for new and renewed passports to arrive. Passports must be valid six (6) months AFTER the date of return to the USA.
Purchase Travel Insurance
ProRome Tours will send you an insurance quote as soon as you register. We strongly suggest that everyone purchase travel insurance.
Prepare Physically
We recommend that pilgrims start walking to prepare for the physical demands of this pilgrimage. We will take the bus whenever possible, but this trip will include approximately 4-7 miles walking, spread throughout the duration of each day.
Pre-Trip Video
Approximately two months before departure, ProRome Tours will send a preparatory pre-trip video to all participants regarding their pilgrimage.
Welcome Boxes
Approximately one month before departure, ProRome Tours will send welcome boxes to all trip participants. Items include: name tags, luggage tags, final detailed itineraries and more.
Final Trip Information
Two weeks before departure, ProRome Tours will email each pilgrim the final trip information, which will include the final detailed itineraries, the rooming lists, the e-ticket numbers for your flights (if booked through ProRome) and any other pertinent trip information.
Pricing, Payments & Cancellation
Additional Information
Trip Patron
As our trip patron, we will pray to St. John Paul II before and during the trip, asking this incredibly holy man for his intercession and protection upon our pilgrimage!
