On Pilgrimage

Musings after 630 days

As I write this, it has been 630 days since I have been in Rome. I recognize how spoiled it seems to complain about that, for a number of reasons. There has been far greater suffering in the world over the last 630 days than my lack of international travel. In addition, some have never had the grace to visit the Eternal City, and my annual travel there was an enormous undeserved gift. That being said, I am itching to be back, and, God willing, I’ll be there soon. (Since life is subject to change these days, I won’t believe it’s happening until I walk into St. Peter’s Square.)

Regardless of whether we can freely move about the country or the world, however, we find ourselves on pilgrimage. Life is a pilgrimage. And I believe seeing life this way helps us deal with what we face daily - whether it’s a pandemic, social unrest, cultural disintegration, or personal struggles. (It’s the subject of one of my favorite talks to give to parishes.) 

The idea of a “pilgrim” comes from the Latin peregrinus, which means a traveler, or one from abroad. But when we look at the idea of a pilgrimage, a pilgrim isn’t just any traveler. A pilgrim is seeking God. Pilgrimages are spiritual journeys - tangible, outward signs of an inward desire of conversion and growth in holiness. 

Our Jewish fathers in faith made pilgrimages up to Jerusalem three times a year (the feasts of Passover, Pentecost, and Booths). They would sing the pilgrimage Psalms (Psalm 122 is a great example) as they traveled up to the holy City of David. After the coming of Christ, Christians traveled to Jerusalem as well, walking in the footsteps of Christ, praying where He died and rose again. 

They began traveling to the tombs of the saints, like St. James in Spain or Sts. Peter and Paul in Rome. Therefore, as modern pilgrims, we are walking not only in the footsteps of Peter and Paul, but also in the footsteps of countless saints who have made the same pilgrimage - Sts. Cyril and Methodius, St. Francis, St. Dominic, St. Catherine of Siena, St. Philip Neri, St. Therese of Lisieux, and others.

These trips were usually undertaken at great expense and with great risk, enduring discomfort – even walking barefoot. While the modern pilgrim might not take on the same risks as the medieval pilgrim traveling across Europe, there is still the opportunity of enduring the modern inconveniences of travel with a cheerful smile. Those brave medieval pilgrims will be on my mind as I navigate the airports and new rules for travel, holding my breath for the unexpectedness around every turn. 

It is important to remember that a pilgrimage is not the same as a vacation. Many travel companies offer trips to Rome. Perhaps you'll walk through St. Peter’s Square or even visit the Vatican Museums. But a pilgrimage is not the same as simply a trip to Rome with a prayer in St. Peter’s. 

A pilgrimage is a spiritual journey. Don’t get me wrong - we have fun on our trips. We stay in nice hotels and eat good food. We experience the culture of the place, and for me in Rome, that usually includes daily gelato. But pilgrimages are not about checking off a scorecard of Roman sites. It's not about getting pictures of every major landmark. It’s not about what you can Instagram (sorry, all you Catholic influencers). 

It’s about making a trip intentionally. Pilgrimages are made for a variety of reasons, including to do penance for one’s sins, to make petition to God, or out of thanksgiving for answered prayers and blessings. While many people sign up for pilgrimages simply because they want to see Italy - and why not see it with some Catholics? - I encourage them to come intentionally. Bring a petition (or two). Ask friends and families for their prayer requests. Make it an intentional trip to thank God for what He has done in your life. Make the trip a prayer.

It doesn't mean we’ll be praying every single moment, although we do go to Mass daily and visit a lot of churches. But the entire movement of pilgrimage should become a prayer, done with intention. That glass of green sambuca after dinner? Raise it up for the greater glory of God, in thanksgiving for a great day and abundant blessings. That annoying bus strike or unexpectedly closed church? Offer it up as a pilgrimage sacrifice. 

A pilgrimage is not a vacation. It’s a microcosm of life.

One of the earliest places we find the word pilgrim used in the Church is when Saint Augustine describes the life of the Christian – our spiritual journey – as a type of pilgrimage.

In life, we travel through this valley of tears – with all the struggles and sufferings that we might have to endure to stay faithful to God amidst temptation and the allures of the world. When you embark on a pilgrimage, you are manifesting outwardly the inward, spiritual disposition that we Christians have throughout our entire lives of conversion.

Life is a pilgrimage – thank heavens. Because we all know that we have some curves in the highway. There are speedbumps. We sin. We may leave the Church for a time. Those things don’t have to define our lives. We keep walking. We keep converting.

That is the journey of the Christian.  Any Christian pilgrimage is supposed to be an image of the great pilgrimage of our life.  They are moments where we step out of our comfort zone, out of our routine, to encounter the living God.  Pope Benedict pointed out that pilgrimages are not just to see art or historical sites.

“To go on pilgrimage really means to step out of ourselves in order to encounter God where he has revealed himself, where his grace has shone with particular splendor and produced rich fruits of conversion and holiness among those who believe.”

A pilgrimage is full of hardship and joy, sacrifices and blessings, focused simultaneously on the journey but most especially the destination.  Beginning with our baptism, we are on a pilgrimage through this temporary homeland, our eyes set on our heavenly home.  Pope Francis reminds us, “Always remember this: life is a journey. It is a path, a journey to meet Jesus.”


So over the next week, I’ll be on pilgrimage. For several of my own special intentions. For your intentions. In thanksgiving for one of the hardest and most rewarding years of my life.

Please pray for Mountain, me, and our group, as we begin our pilgrimage. If you’ve never considered a pilgrimage, pray about that, too. You won’t regret it. Mountain and I are currently planning at least one Rome pilgrimage next spring, and we’d love to have you along.

Leading people on pilgrimage is one of my favorite things in the world. You might assume it’s my favorite because it means traveling to Europe, seeing the Pope, and eating good food. Those are great things, and things that I've missed terribly. But you know what I've missed more?

Experiencing people experiencing. I love to be part of people’s pilgrimages. Everyone brings their own stuff. Some of it gets worked out; some of it doesn’t. But it’s there. We're there. And it’s a life-changing experience.

I get to pray with people as they climb the Holy Stairs on their knees for the first time. I get to see people reach out to touch the Pope as he drives by. I get to witness the joy of people praying in front of the Crib of Our Lord and weep as they see the relics of the Passion. 

Each time I take a group over to Rome, I’m shaken out of my own jadedness towards the Eternal City. Anyone who knows me knows I can’t express my love for Rome enough. But familiarity breeds complacency. As the trip approaches, I calm the jitters and answer the questions from people who have never traveled abroad. Both their excitement and concern reminds me of the importance of pilgrimage – something that I fear I take for granted.  Packing for Rome is little different than packing for the East Coast for me, and I can almost do it in my sleep.  I need the reminders of the pilgrims in my charge to awaken me.

That is why I love to experience people experiencing Rome. It’s become almost a second home for me, and although each trip has always involved seeing something new, mostly I will revisit places I have been dozens and dozens of times. But I will go there anew – because I will go there with others, some whom have never been there. I will witness people praying at the tombs of their confirmation saints. I will see people gaze at the Sistine Chapel for the first time. I will get to see the successor of St Peter with people who have only seen him through a screen.

These experiences are an important part of one’s faith formation. In my new apostolate, I speak and write and teach. But these pilgrimages provide formation in a way sitting in a classroom or listening to a podcast never can.  Touching the Catholic faith as one does on pilgrimage is life-changing.  I was abundantly blessed to have parents who realized importance of this, even to the point of taking me out of school for two weeks so that I could travel to France and Italy.  At only fifteen years old, I stepped into St. Peter’s Square for the first time. And although I didn’t know it then, my life would never be the same.  

Not everyone has the chance to travel to Europe, and I know that for many, something like seeing the Pope or praying at these sites might always remain on the bucket list. That is why I must never, ever take it for granted. I must never become jaded at the sight of Michelangelo’s dome, rising over the rooftops of Rome.  I must never tire of walking through the Forum on Via Sacra, my steps tracing the steps of our first Pope and St. Paul.  I must never lose the joy I had that very first time I walked into the loving embrace of Bernini’s colonnade.

That is why I bring others. Because I have to experience it for the first time – again.

If you’re interested in traveling on pilgrimage with me and The Catholic Traveler, let me know. And until then, know of my prayers and please pray for me.