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Pilgrimage to Italy with Fr. Andrew Jones and Fr. Peyton Plessala

  • May 6 – 14, 2027
  • From $2,950
  • Limited spots available

Have questions?

We’re here to help! Call or email one of our pilgrimage specialists today.

(800) 653-0017

hello@canterburypilgrimages.com

Mon-Fri | 9am – 5pm ET

Your Pilgrimage Package

What's Included

  • 4-star hotels (2 nights Assisi, 5 nights Rome)
  • Licensed guiding & admission fees
  • Breakfast daily plus two group dinners: a welcome dinner in Assisi and a farewell dinner in Rome
  • Audio headsets when touring
  • Wine served with group dinners
  • Tips for restaurant and hotel steff
  • Daily Mass & spiritual activities
  • Private Masses, including St. Peter's Basilica
  • Name badge & luggage tag
  • Papal General Audience tickets
  • Private motorcoach transportation
  • Copy of the Magnificat
  • 9am-5pm ET reservation support
  • Professional tour manager
  • 24-7 travel emergency support
  • Copy of the Canterbury Tales

What's Not Included

  • Tips for your tour director & bus driverFor exceptional service, tip your tour director €7 per day and bus driver €2 per day (at the end of the pilgrimage)
  • LunchesThere will be time each afternoon to make your own culinary decisions! (~$15/day)
  • Travel insuranceIt's highly reccommended and vailable at registration (cost is dependent on your trip cost & age)
  • The cost of meeting any national entry requirementsIncluding but not limited to the cost of applying for or renewing a passport, the cost of a visa (if necessary), etc.
  • Anything not mentioned as includedDonations at Masses, souvenirs, laundry, pet-sitting, spontaneous pastries, emergency shoe laces, extra holy water, your 5th espresso of the day, postcards for everyone back home, and all other earthly desires not mentioned above!

Pilgrimage Itinerary

May 6, 2027 | Depart from the United States

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.

 

May 7 |  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 to Assisi, the hill town of St. Francis and St. Clare. After check-in, we gather this evening for a welcome dinner to begin our pilgrimage together. Overnight in Assisi. (D)

 

May 8 | Assisi, St. Clare, St. Carlo Acutis, San Damiano & the Porziuncola

Today is given entirely to Assisi. We begin at the Basilica of St. Clare, resting place of the foundress of the Poor Clares, where we venerate her incorrupt body and pray before the San Damiano Cross, from which St. Francis heard the call to rebuild the Church. A short walk brings us to the Sanctuary of the Renunciation, the Church of Santa Maria Maggiore, where we venerate the tomb of St. Carlo Acutis, the first millennial to be canonized, a boy of fifteen who called the Eucharist his highway to heaven and who died of leukemia in 2006. We continue to the Basilica of St. Francis, where we celebrate Mass at the tomb of the Poverello, whose radical embrace of poverty and love of creation continue to inspire the Church eight centuries later, and view Giotto’s frescoes of his life. After time for lunch and quiet prayer in the upper town, we descend to the Church of San Damiano, where the crucifix spoke to St. Francis and where St. Clare and her sisters lived out their days, still among the most peaceful corners of Assisi. We conclude at the Basilica of St. Mary of the Angels, built around the tiny Porziuncola chapel so beloved of St. Francis, and see the Cappella del Transito, marking the spot where he died in 1226, along with the thornless rose garden associated with his victory over temptation. The evening is our own in Assisi. Overnight in Assisi. (B)

 

May 9 | Assisi to Rome, San Clemente & the Colosseum

After breakfast we take leave of Assisi and travel south through Umbria to Rome, where we check in to our hotel for the remainder of our pilgrimage. This afternoon we celebrate Mass at the Basilica of San Clemente, entrusted to the Irish Dominicans, a church built in three layers: a twelfth-century basilica crowned by a golden mosaic of the Cross as the Tree of Life, above a fourth-century church that holds the relics of St. Clement, third successor of St. Peter, and the tomb of St. Cyril, apostle to the Slavs, and beneath that a first-century Roman house. A short walk brings us to the Church of St. Peter in Chains, where we venerate the very chains tradition holds bound St. Peter during his Roman imprisonment, and pause before Michelangelo’s imposing Moses. We come down to the Colosseum and walk its perimeter, where tradition holds that early Christians gave witness to their faith even unto death, pausing at the neighboring Arch of Constantine, raised in honor of the emperor whose Edict of Milan in 313 ended centuries of persecution and opened the way for the Church to flourish. From there we walk the length of the Via dei Fori Imperiali toward Piazza Venezia, the Roman Forum lying open below us on one side and the forums of the emperors on the other, finishing in view of Trajan’s Column and the Victor Emmanuel Monument. The evening is at leisure. Overnight in Rome. (B)

 

May 10 | St. Peter’s Basilica, the Vatican Museums & the Sistine Chapel

This morning we celebrate Mass at St. Peter’s Basilica, the largest church in Christendom, raised over the tomb of the fisherman to whom Our Lord entrusted the keys, and we remain afterward to pray at the tombs of the Apostle and of St. John Paul II and to pause before Michelangelo’s Pietà, a moving meditation on Our Lady cradling her crucified Son. We then enter the Vatican Museums, home to one of the world’s great collections of sacred art, passing through the Gallery of Maps and the Raphael Rooms and concluding in prayerful silence beneath Michelangelo’s frescoed ceiling in the Sistine Chapel. The evening is at leisure. Overnight in Rome. (B)

 

May 11 | The Old Appian Way, the Catacombs of St. Callixtus & St. Paul Outside the Walls

This morning we journey out along the Old Appian Way, the ancient road walked by the earliest Christians and, tradition holds, by St. Peter himself as he fled Rome, pausing at the little church of Domine Quo Vadis. We descend into the Catacombs of St. Callixtus and celebrate Mass amid the same underground galleries where the early Church buried her dead, among them the Crypt of the Popes and the tomb of St. Cecilia. We visit the Basilica of St. Paul Outside the Walls, raised over the tomb of the Apostle to the Gentiles, whose nave is ringed by mosaic medallions of every pope from St. Peter onward. This afternoon we visit the Church of Santa Maria della Vittoria, where Bernini carved his Ecstasy of St. Teresa, his rendering of the Carmelite reformer’s own account of the wounding of her heart, and the neighboring Church of St. Charles at the Four Fountains, Borromini’s small masterpiece dedicated to St. Charles Borromeo. The evening is at leisure. Overnight in Rome. (B)

 

May 12 | Papal Audience, St. John Lateran, the Holy Stairs & the Holy Cross in Jerusalem

This morning we attend the General Papal Audience in St. Peter’s Square and receive the Holy Father’s Apostolic Blessing. This afternoon we visit the Basilica of St. John Lateran, the cathedral of the Diocese of Rome, whose facade proclaims it the mother and head of all the churches of the city and of the world. Across the street we come to the Scala Sancta, traditionally believed to be the very steps Our Lord climbed to the praetorium of Pontius Pilate, brought to Rome by St. Helena and ascended by pilgrims on their knees in prayer, and we look into the Sancta Sanctorum, the private chapel of the medieval popes. We celebrate Mass at the Basilica of the Holy Cross in Jerusalem, raised within St. Helena’s own imperial residence to house the relics she brought back from the Holy Land, among them fragments of the True Cross, the title board that hung above Our Lord, and a nail. The evening is at leisure. Overnight in Rome. (B)

 

May 13 | St. Mary Major & the Churches of Old Rome

We open the day with Mass at the Basilica of St. Mary Major, the oldest church in the West dedicated to Our Lady, where we venerate the relic of the Holy Crib and the ancient icon of Salus Populi Romani, so beloved of the popes, and pray at the tomb of Pope Francis. The rest of the day belongs to the churches of old Rome, which we visit on foot. We begin at the Church of the Gesù, mother church of the Society of Jesus, where St. Ignatius of Loyola lies beneath the altar of his chapel and the arm of St. Francis Xavier is venerated. We continue to the Church of St. Ignatius, whose vault carries Andrea Pozzo’s soaring painted heavens and whose celebrated dome is an illusion painted on flat canvas, and where St. Aloysius Gonzaga and St. John Berchmans are buried. At Santa Maria sopra Minerva, Rome’s great Dominican church, we venerate the body of St. Catherine of Siena, Doctor of the Church and co-patroness of Europe, and pause at the tomb of Blessed Fra Angelico. Steps away stands the Basilica of St. Mary and the Martyrs, better known as the Pantheon, an ancient temple given to the Church in 609 and consecrated to Our Lady and all the martyrs. We continue to the Church of St. Louis of the French, home to Caravaggio’s paintings of the calling, inspiration and martyrdom of St. Matthew, and to the Church of St. Augustine, where the tomb of St. Monica rests near Caravaggio’s Madonna of Loreto and Sansovino’s Madonna del Parto. We pause in Piazza Navona before concluding at the Chiesa Nuova, the church of St. Philip Neri, apostle of Rome, where we pray at his tomb and see the rooms in which he lived. This evening we gather for a farewell dinner at Ristorante Abruzzi, near the Pontifical Gregorian University (pending availability). Overnight in Rome. (B/D)

 

May 14 | Return Home

With hearts renewed by the grace of pilgrimage and by the intercession of St. Francis and St. Clare of Assisi and the Apostles Peter and Paul, we transfer to Rome’s Fiumicino Airport for our return flight home to the United States. (B)

Pricing

Double Room

2 guests
$2,950/per person

Single room

1 guest
$+699/per person

Payment Schedule

Today
$450 due per person
$200 per person is non-refundable.
02/05/2027
Remaining payment due
The initial deposit of $450 plus any charges imposed by our vendors is non-refundable. In the event of postponement, this still applies. Payment plans are available if you would like to make smaller payments prior to the final payment date.

Payment Options

Paying by Credit or Debit card

Pay online through your reservation or call (800) 653 – 0017 to pay by card | 3% CC fee

Paying by check

Mail your check to the following address and include your reservation # on the memo line.

401 E Las Olas Blvd Suite 130-478, Fort Lauderdale, FL 33301

Paying by ACH Bank Transfer

Call (800) 653 – 0017 or email hello@canterburypilgrimages.com to receive a secure Bank Transfer link via email

Paying by Zelle

Find Canterbury Pilgrimages by using our email | hello@canterburypilgrimages.com

Paying by cash, money order or cashier check

You can deposit cash, check, money order or cashier check in person at any Bank of America.

Please call (800) 653 – 0017 or email hello@canterburypilgrimages.com to receive more instructions

Know Before You Book

What is a pilgrimage?

What is a pilgrimage?

We would like to remind you that a pilgrimage is not a vacation or excursion but rather a unique spiritual journey that will provide many opportunities to deepen your relationship with God and enrich your Catholic faith by bringing Scripture to life. Millions throughout the ages have gone before you searching for a way to physically connect with their faith in Christ Jesus. You may find that when you are near a saint’s tomb, viewing a holy relic, or praying a Marian devotion, you are overwhelmed by the Holy Spirit in a very real sense. Pilgrimages offer the opportunity to let Christ draw you near. Your chaplain is there to help guide you spiritually on this journey.

Walking expectations

This active program covers a good amount of ground each day. The days are busy, usually starting with a wake-up call around 7AM and departure by 9AM or earlier. We aim to be back at the hotel between 5PM and 6PM. Times may vary depending on destination and program. We encourage all pilgrims to be able to walk 3-4 miles per day. The pace is moderate, however you will encounter some uneven surfaces, stairs, steps, cobblestones, and significant slopes. Some tours require walking in the open air with no shade and no seating available. For more specifics on this itinerary’s physical landscape, please reach out to us.

Pilgrimage Timeline with Canterbury

Today! Registration

Upon depositing for your trip, we would like to get to know a little bit about you. We will collect your basic contact information, passport information, emergency contact information, and how you would like to set up your pilgrimage. How many are in your party? Will you travel with them and/or share a room with them? Do you know anyone else attending? Where are you flying from?

After Registration

You will receive additional information that will help you start preparing for your pilgrimage. If applicable, we will also begin working on your flight and travel requests.

90 days – Payment deadline

Full payment is due for your trip 90 days prior to your departure. This also serves as the last day to sign up for the pilgrimage if space is still available. Once within the 90-day deadline, we may be able to accommodate you at a different rate.

30 days – Pilgrim travel kit mailed

Your pilgrim travel kit includes an invite to download our travel app. On the app is where you will find your flight itinerary (if you opt for us to book your flights), trip itinerary, and a map of your hotel accommodations. You will also have the ability to share photos and messages with fellow pilgrims, and receive any important flight and schedule updates before and during your pilgrimage. Also included in the pilgrim travel kit is your name badge, a luggage tag, a Magnificat prayer book, and a copy of the Canterbury Tales by Chaucer, which inspired our mission.

Your pilgrim travel kit will either be delivered to your mailing address provided, or to your parish if a pre-departure meeting is arranged. Please note, we ship via FedEx 2-day air, and thus cannot deliver to P.O. boxes.

Departure Day

The day has arrived! We are looking forward to meeting you.

Upon Return

After the pilgrimage experience, we would love to hear from you what went well and what we can improve upon. We kindly ask you to respond to the survey in your inbox within 5 days of return while your new memories are still fresh.

Time to book your next pilgrimage!

See all of our current pilgrimage offerings here!

Hotel Accommodations

Single Rooms

Solo travelers are always welcome on our pilgrimages. If you wish to have a hotel accommodation to yourself, you will be responsible for the single room fee (commonly referred to as a single supplement.)

Shared Rooms

Sharing hotel accommodations is a great way to save money and get to know another solo traveler on the pilgrimage. If you wish to share a room, we will attempt to connect you with another person of the same gender on the pilgrimage looking to share. Shared rooms are always double rooms with 2 beds. Should we not be able to accommodate you with a roommate, you will be responsible for the single room fee.

Double Rooms

For pilgrims traveling with a companion, double rooms are available in either 1 or 2 bed configurations.

Triple & Quad Rooms

For pilgrims traveling in parties of 3 or 4, please be aware that while we do our best to accommodate, not all hotels have rooms equipped with 3 or 4 beds. In many cases, the 3rd or 4th bed is a cot or convertible sofa bed.

Bed Sizes

Europe: 1 queen bed or 2 twin beds

Asia: 1 twin bed or 2 twin beds

USA: 1 king bed or 2 queen beds

Passports & Visas

Passports

  • A valid passport is required to travel outside of the United States.
  • Your passport must be valid 6 months from the trip return date.
  • If your passport will be expiring within the 6 month window, it is important to renew your passport in a timely manner as renewal turnarounds can take several weeks to months.
  • Passport cards are NOT acceptable for travel internationally; only passport books.
  • We will need your passport information at least 90 days prior to departure. You may provide us with your passport information upon registering if it is valid and up to date.
  • All airlines and hotels require us to submit your passport information including full name, date of birth, gender, country, and passport expiration date.

Although we will do our best to notify you if your passport will not be valid for travel, it is ultimately your responsibility to ensure your passport is valid.

Travel Visas

Depending on the nationality of your passport, a travel visa may be required to reach your destination. Although we will do our best to notify you if a travel visa is required, it is ultimately your responsibility to check if visas are required for the destinations visited and to obtain any necessary travel documents. You can do that easily here: https://apply.joinsherpa.com/travel-restrictions

Travel Insurance

Travel Insurance

  • We strongly encourage travel insurance for all of our pilgrims. We partner with Allianz Travel Insurance to offer affordable travel insurance.
  • Most of our pilgrims choose the Classic Plan to protect their travel investment. Learn more about this plan by clicking here.
  • Insurance can be quoted and purchased after registration. With any questions, or if you would like to include insurance for airfare or accommodations that you did not purchase through Canterbury, please contact us for assistance.
  • By purchasing a policy through us, please note that the service we provide is only in the acquisition and management of your policy. In the case of postponement or cancellation of your pilgrimage, we will request the necessary updates to your policy to reflect your new dates of travel, or request the cancellation and refund of your insurance policy if applicable (refunds are subject to Allianz’s discretion). Any claims filed are the responsibility of the customer.

Accessibility

In the air

Although group airfare is restrictive with seat selection, we will always do what we can to accommodate pilgrims who need specific seating, such as aisle or bulkhead seating, due to a medical condition or disability. In addition to that, wheelchair assistance from the moment you arrive at the airport, to your terminal, or all the way to your seat, is available to you, provided by the airline, and does not need to be pre-arranged.

On the ground

Most countries do not follow US accessibility standards. Old buildings, cobblestone walkways, and uneven surfaces are a part of every itinerary. Access to some establishments may not be convenient for wheelchair use and will require the use of stairs. During hotel overnights, we can arrange for you to stay in handicap-accessible rooms where available. In the event they are not available, we will request rooms on the main floor or near an elevator.

Can I request a wheelchair?

Pending availability, we are happy to request a wheelchair rental for the duration of the pilgrimage. Wheelchair users must have a designated travel companion to assist them during the pilgrimage. Please reach out to us to place this request.

Postponements & Cancellations

Postponement

We always intend to provide our customers with the pilgrimage they spend time and resources to plan with us. If we are unable to travel to a destination ahead of a trip, or reasonably predict to be unable to travel, Canterbury reserves the right to make changes to the itinerary, including the dates of the trip. We respect your time and that of the people in your life who plan for your absence. We only change or postpone the dates of the trip when it is necessary due to inability to travel to a destination, untimely closures in crucial sites along the itinerary, extreme weather conditions, government mandates, war, acts of God, or other factors. In this situation, your reservation will be automatically preserved for the new dates of the trip, which will take place at a reasonable time arranged by Canterbury and/or the group organizer. Additionally, Canterbury hopes to offer you the best possible options for your reservation given the circumstances, which, if possible, could include transferring your reservation to another trip, or other arrangements.

Cancellation

Countless months get put into the organization of your trip, thus we do our best to avoid cancelling it. Though we reserve the right to cancel for any reason at any time, we typically only do in instances of an insufficient group size. In this case, we would refund 100% of what you have paid to us back to your original payment method on file within 10 business days.

Reserve Now
Pilgrimage to Italy with Fr. Andrew Jones and Fr. Peyton Plessala

Have questions?

We’re here to help! Call or email one of our pilgrimage specialists today.

(800) 653-0017

hello@canterburypilgrimages.com

Mon-Fri | 9am – 5pm ET