Assisi & Rome Pilgrimage with Fr. Connor Plessala
Ten days with Fr. Connor Plessala: Mass at the Basilica of St. Francis, the tomb of St. Carlo Acutis, the feast of St. Aloysius in Rome, the Papal Audience and the Scavi beneath St. Peter’s.
Your chaplain
Fr. Connor Plessala
Vocations Director, Archdiocese of Mobile, and Chaplain, St. Michael Catholic High School, Fairhope, Alabama
“You are Peter, and upon this rock I will build my church.”
Matthew 16:18
The words written around the dome of St. Peter’s Basilica, where we celebrate Mass on Day 8, above the tomb of the Apostle we visit in the Scavi on Day 9.
Day eight · Tuesday, June 22 · St. Peter’s Basilica, Vatican City
Assisi & Rome, June 15 to 24, 2027
Ten days, eight nights: three in Assisi and five in Rome, with Mass each day. The Scavi Tour on Day 9 is subject to availability from the Vatican Excavations Office.
Begins at Rome Fiumicino Airport and ends in Rome
OvernightVisit
Nights: 3 Assisi, 5 Rome.
Departure
Our pilgrimage begins as we depart the United States on our overnight flight to Rome, Italy. Dinner and breakfast will be served during the flight.
Arrival in Rome & Transfer to Assisi
Upon arrival at Rome’s Fiumicino Airport, our local professional tour escort will greet us and accompany us by motorcoach through the Umbrian countryside to Assisi, the hill town of St. Francis and St. Clare. After check-in, the afternoon is free to rest after our journey. This evening we gather for a welcome dinner to begin our pilgrimage together.
St. Francis, St. Clare & the Porziuncola
We begin the day in prayer at the Basilica of St. Francis, where we celebrate Mass in the town where the Poverello was born, converted, and laid to rest. Begun in 1228, the year of his canonization, the basilica rises in two levels above his tomb. Our guided visit leads us through the Upper Basilica, whose fresco cycle traditionally attributed to Giotto tells the story of his life, and down to the crypt, where we kneel at his tomb and entrust our intentions to his intercession. We then walk through the medieval streets of the upper town to the Sanctuary of the Renunciation at the Church of Santa Maria Maggiore. Here the young Francis stripped off his fine clothes before the Bishop of Assisi and renounced his inheritance to belong to God alone, and here we venerate the tomb of St. Carlo Acutis, the young apostle of the Eucharist canonized in 2025 as the first millennial saint. We continue across town to the Basilica of St. Clare, where we venerate the body of the foundress of the Poor Clares and pray before the San Damiano Cross, the very crucifix that spoke to St. Francis and called him to rebuild the Church. After lunch, we descend into the valley to the Basilica of St. Mary of the Angels, raised over the Porziuncola, the tiny chapel St. Francis restored with his own hands and where the Franciscan Order took root. We pray in the Chapel of the Transitus, marking the spot where he died in 1226, before returning to our hotel.
Eremo delle Carceri & San Damiano
Today is devoted to the quiet places where St. Francis prayed. After breakfast we make our way up the wooded slopes of Mount Subasio to the Eremo delle Carceri, the hermitage where St. Francis and his first companions withdrew for long seasons of solitude and prayer, and where we see the small grotto in which he rested and prayed. In this peaceful setting we celebrate Mass and take time for personal reflection. After lunch in Assisi, we walk down through the olive groves below the town walls to the Church of San Damiano. It was here that the crucifix spoke to the young Francis, “Go, repair my house,” and here that St. Clare and her sisters lived their life of poverty and prayer for more than forty years. St. Clare died at San Damiano in 1253, and St. Francis composed his Canticle of the Creatures here. The remainder of the afternoon is free for prayer in Assisi’s churches before we return to our hotel, and the evening is free for dinner on our own.
Catacombs of St. Callixtus & St. Paul Outside the Walls
After breakfast we bid farewell to Assisi and travel by motorcoach to Rome. We follow the ancient Appian Way to the Catacombs of St. Callixtus, the first official burial ground of the Church of Rome, where we descend into the galleries that hold the Crypt of the Popes and the place where St. Cecilia was first laid to rest. Here, amid the tombs of the early Christians and martyrs, we celebrate Mass. We continue to the Basilica of St. Paul Outside the Walls, one of Rome’s four Papal Major Basilicas, raised over the tomb of the Apostle to the Gentiles. We pray before his tomb beneath the high altar and see the chains traditionally venerated as those that bound him in prison. We then check into our hotel, with time to rest. The evening is free for dinner on our own.
The Colosseum, St. John Lateran & St. Mary Major
On this Sunday morning we pause outside the Colosseum, the great amphitheater of ancient Rome, where tradition holds early Christians gave witness to their faith even unto death, and where the Holy Father traditionally leads the Way of the Cross on Good Friday. A short walk brings us to the Basilica of St. John Lateran, the cathedral of the Bishop of Rome and mother and head of all the churches of the city and the world, consecrated in the fourth century in the time of Constantine, where we celebrate Holy Mass on the Lord’s Day. Across the square we visit the Scala Sancta, the Holy Stairs, traditionally believed to be the very steps Christ climbed on his way to judgment before Pontius Pilate, which pilgrims ascend on their knees in prayer. We continue to the Basilica of the Holy Cross in Jerusalem, founded within the palace of St. Helena, where we venerate relics traditionally honored as fragments of the True Cross, a nail of the Crucifixion, and the title board that hung above Our Lord’s head. From there we walk to the Basilica of St. Mary Major, rebuilt by Pope Sixtus III after the Council of Ephesus proclaimed Mary the Mother of God in 431. Here we pray before the ancient icon of Our Lady, Salus Populi Romani, venerate the relic of the Holy Crib, and visit the tomb of Pope Francis. The evening is free for dinner on our own in the nearby Monti neighborhood.
Feast of St. Aloysius & the Churches of the Centro
Today the Church keeps the feast of St. Aloysius Gonzaga, patron of youth, and we spend it in the historic heart of Rome among the saints of the Society of Jesus. We celebrate Mass at the Church of Sant’Ignazio, raised in honor of St. Ignatius of Loyola after his canonization in 1622, where St. Aloysius rests near his confessor, St. Robert Bellarmine, Doctor of the Church, and across from the young St. John Berchmans. St. Aloysius died in Rome in 1591 at the age of 23 after caring for the sick during a plague, and on his feast the rooms where he lived as a student at the Roman College are opened to pilgrims. A short walk brings us to the Church of the Gesù, the mother church of the Society of Jesus, where we pray at the tomb of St. Ignatius and venerate the right arm of St. Francis Xavier, the great missionary to Asia, the arm with which he baptized countless converts. We continue past the Pantheon to the Basilica of Sant’Agostino, where we pray at the tomb of St. Monica, whose years of tears and prayer won the conversion of her son, and pause before Caravaggio’s Madonna of Loreto, which shows two humble pilgrims kneeling at Our Lady’s feet. Our walk concludes in Piazza Navona, laid out over the ancient stadium where tradition holds the young St. Agnes gave her life for Christ, at the Church of Sant’Agnese in Agone, which preserves the relic of her skull. The afternoon is free to rest or to explore Rome at leisure, and the evening is free for dinner on our own.
St. Peter’s Basilica, Vatican Museums & Sistine Chapel
We rise early this morning to celebrate Mass at St. Peter’s Basilica, the largest church in Christendom, raised over the tomb of the fisherman St. Peter, Prince of the Apostles. On our guided visit of the basilica we pause in prayer before Michelangelo’s Pietà, at the tomb of St. John Paul II, and beneath Bernini’s soaring bronze canopy above the tomb of St. Peter. We then have time in the Borgo Pio, the lanes beside the Vatican, to purchase rosaries, medals, and other sacramentals to be blessed during our pilgrimage. In the afternoon we enter the Vatican Museums for a focused visit along the route to the Sistine Chapel, where we stand in prayerful silence beneath Michelangelo’s frescoed ceiling and his Last Judgment, in the chapel where the College of Cardinals gathers in conclave to elect the successor of St. Peter. The evening is free for dinner on our own.
Papal Audience, the Scavi & Rome by Night
This morning we make our way to St. Peter’s Square to join pilgrims from around the world for the General Audience with the Holy Father, receiving his Apostolic Blessing for ourselves, our loved ones at home, and the religious articles we carry. Following the Audience, we celebrate Mass in Vatican City. This afternoon we descend beneath St. Peter’s Basilica for the Scavi Tour, a guided visit through the excavated Roman necropolis on the Vatican Hill, where St. Peter was buried after his martyrdom. The tour leads us to the tomb of the Apostle beneath the high altar, where in 1968 Pope St. Paul VI announced that bones identified as those of St. Peter had been found, and we pray at the very foundation on which the Church in Rome was built. This evening we gather for a farewell dinner at Ristorante Abruzzi, a family trattoria beside the Basilica of the Twelve Apostles, and then pause at the Trevi Fountain before walking back to our hotel through the lamplit streets and piazzas of the Eternal City.
Rome, Return Home
With hearts renewed by the grace of pilgrimage and the intercession of St. Francis and St. Clare of Assisi and the holy Apostles Peter and Paul, we transfer to Rome’s Fiumicino Airport for our return flight home to the United States.
What’s included
Everything below is covered by the package price.
Your hotels in Assisi and Rome
Three nights in Assisi and five nights in Rome, in three-star hotels. Hotels are subject to final confirmation; if a hotel changes, it is replaced with one of the same standard.
“Each site was thought out about why and how to pray there.”
“Each one has been beautifully arranged and managed from start to finish.”
“Thank you for taking care of the day to day details, leaving all of us free to focus on prayer and spiritual growth”
Price per person
Per person, including roundtrip group airfare from Pensacola (PNS). Flying from another city? You can request an airfare quote from your airport when you reserve.
$200 per person is non-refundable.
Final payment is due 90 days before departure and is non-refundable. Payment plans are available if you would like to make smaller payments before then.
Check
ACH bank transfer
Zelle
Cash, money order or cashier’s check
Protect your pilgrimage
Your pilgrimage is paid for long before you leave. Travel insurance is added as part of your booking: when you reserve, choose an Allianz plan on the insurance step. There is no separate quote to get. Classic is the plan we recommend for most pilgrims.
- Covers your trip cost. Classic reimburses 100% of the trip cost you insured if you cancel for a covered reason, and adds emergency medical care and baggage cover.
- Buy within 14 days of your first deposit to keep Cancel Anytime and pre-existing condition cover. The plans stay available until departure.
- Buy it in the same checkout as your pilgrimage. Prefer to add it by phone? Call us at +1 (800) 653-0017.
Frequently asked questions
Expect about 2 to 3 miles of walking on a typical day, much of it on cobblestones. Assisi is a hill town with steep streets and steps, and on Day 4 we walk down through the olive groves to San Damiano. The Rome days include walks between churches and a good deal of standing in the basilicas and the Vatican Museums, and Day 9 starts early for the Papal Audience.
You can have a room to yourself with the single room supplement of $550, or share a room with two beds with another pilgrim. If you would like to share, we will do our best to match you with a roommate; if we cannot find a match by the final payment date of March 17, 2027, the single room supplement applies. Couples, families, friends and singles are all welcome, and plenty of pilgrims come on their own.
Lunches, dinner on the five free evenings (Days 4 to 8), donations at Masses, souvenirs and laundry. Tips for your local guides and driver: if you are satisfied with their service, it is customary to tip. Tips for hotel and restaurant staff are already included. Add travel insurance if you choose it, and the 3% fee if you pay by credit card. A typical lunch costs about $15 to $20. Abroad, we recommend paying for most things by credit card, which is accepted almost everywhere and comes with protection that cash does not; bring a couple hundred US dollars in cash for emergencies. When a card machine or ATM asks whether to pay in dollars or in the local currency (euros), choose the local currency; it is almost always cheaper.
Yes. Let us know in writing. Up to March 17, 2027, everything you have paid is returned except $200. The final payment, due on March 17, 2027, is non-refundable, so cancellations after that date receive no refund. Travel insurance may cover a cancellation, depending on the reason.
Pilgrims traveling with Fr. Connor Plessala, Vocations Director for the Archdiocese of Mobile, who celebrates Mass for the group each day, and a local tour escort who meets the group on arrival at Rome’s Fiumicino Airport.
Expect warm, sunny days in Assisi and Rome, often in the 80s Fahrenheit, with cooler mornings and evenings in Assisi. Bring sun protection, a refillable water bottle and comfortable walking shoes. Shoulders and knees must be covered in St. Peter’s Basilica, the Vatican Museums and the churches of Assisi and Rome, so pack light clothing that covers them.
Yes. Bring a valid U.S. passport book; a passport card is not accepted for international flights. We recommend a passport valid for at least six months beyond the return date, and we need your passport details at least 90 days before departure. If the EU ETIAS travel authorization is in effect by departure, you will also need it to enter Italy.
The group airfare includes one checked bag, one carry-on and one personal item per pilgrim.
Yes. The price includes roundtrip group airfare from Pensacola (PNS) to Rome; if you book your own flights, the ground-only price is $3,726 per person, two sharing (choose “Book my own” on the flights step when you reserve). Send us your flight details once booked, so we can line your arrival up with the group’s at Rome’s Fiumicino Airport on June 16 and your departure on June 24. Group air from other airports can be arranged; you can request an airfare quote from your airport when you reserve.
Final payment is due on March 17, 2027, 90 days before departure, and is non-refundable. Payment plans are available if you would like to make smaller payments before then.
We strongly encourage travel insurance for all of our pilgrims, and we partner with Allianz Travel Insurance to offer affordable coverage. Most of our pilgrims choose the Classic Plan. You add it as part of your booking: choose a plan on the insurance step when you reserve, or call us at +1 (800) 653-0017. Buy within 14 days of your first deposit to keep Cancel Anytime and pre-existing condition cover.
A pilgrimage is not a vacation or excursion but a unique spiritual journey that provides many opportunities to deepen your relationship with God and enrich your Catholic faith by bringing Scripture to life. Pilgrimages offer the opportunity to let Christ draw you near.
More questions are answered in our Support Center, covering booking, payments, travel insurance, passports and what to expect on pilgrimage.
Assisi & Rome Pilgrimage with Fr. Connor Plessala
June 15 to 24, 2027, with Fr. Connor Plessala of the Archdiocese of Mobile. Reserve today with a $450 deposit per pilgrim.
Questions? Call +1 (800) 653-0017 or email hello@canterburypilgrimages.com.
Secure your spot today with a $450 deposit per pilgrim.