For months, I had been preparing to depart on a trip to Italy for the Jubilee Year and especially the canonization of Blessed Carlo Acutis. The canonization of Blessed Carlo is exciting for me on multiple levels. First of all, he is the first saint that I was familiar with BEFORE he was canonized. More importantly, he used technology to bring the profound beauty of the real presence of Jesus to light for countless internet users through his website documenting Eucharistic Miracles. As a marketer and a connoisseur of digital media, Blessed Carlo was about to become the first saint I felt I could relate to personally. I was anticipating his canonization with great excitement

Then, on Easter Monday, April 21, 2025, I woke up to the news that Pope Francis had passed away.

I converted to the Catholic faith during Pope Francis’s pontificate. He was the only Holy Father I have had, so the loss for me was palpable. I knew that his passing would delay the canonization of Blessed Carlo. The two events together drastically changed the landscape of my upcoming trip, personally and professionally, as I was accompanying a large group of pilgrims traveling to Italy with the Catholic Talk Show. I knew that there would be additional challenges and myriad unknowns. There would certainly be changes.

Semper Gumby

The first days of any pilgrimage are the most challenging. Long hours of travel, jet lag, carrying luggage, finding the group, and meeting all the people on your trip take a lot out of anyone. This time, there was an added level of anxiety in the unknown. Would all the sites we planned to see be open? What would we do instead of attending the canonization? Would we be able to participate in the Holy Father’s funeral? As I stepped off the plane, I initially braced for a wave of questions.

Then I remembered to adopt the Semper Gumby attitude. “Semper Gumby” is an unofficial adaptation of “Semper Flexibilis”, Latin for always flexible.

Remaining flexible on a pilgrimage, especially on the first day, is essential. Months of preparation and the best-laid plans often encounter obstacles in the real world. Weather, traffic, and even the death of a Pope can dramatically change things on the ground. Just as rigid trees break in the wind, rigidity on pilgrimage closes you off to relying on God’s providence, a hallmark of the pilgrimage experience. I was so blessed to meet our group and learn that most embraced the Semper Gumby mentality, and all of them were patient as we gathered answers together.

Orvieto

Our first stop in the mountain town of Orvieto brought us face-to-face with the Eucharistic Miracle of Bolsena. We celebrated Mass with the corporal on display. The profound reality of the real presence emblazoned before us made the length of the flight, the airplane breakfast, and the wait for everyone to arrive worth it. Our pilgrimage began with Mass in the presence of a miracle.

The fact is that Peter of Prague (the German priest who witnessed the Miracle of Bolsena while saying the words of consecration) was not planning on seeing such a miracle. He was troubled by doubts that Christ was present in the Eucharist and had many questions. This miracle helped to change his faith.

How often do we arrive somewhere with an unmet expectation? How frequently do we get angry or frustrated because some small aspect of our day isn’t what we planned? Perhaps Jesus is waiting to reclaim that moment, like He did with Peter of Prague. Eucharistic revival, a new Pope, new saints…It struck me that He may be doing something special in Italy during the Jubilee Year, just like He was with Peter of Prague.

Pilgrims of Hope

When Pope Francis announced the Jubilee Year theme, Pilgrims of Hope, I wondered if he knew that this Jubilee year would bring the beauty of the Succession of St. Peter into complete focus. The death of a Pope is indeed a sad time, a time for mourning, but it’s not the end of the Church. It’s a time of renewal and rebirth as a new Pope is chosen to lead the Church forward. The hope this affords Catholics worldwide has been fully displayed over the past several weeks. The fact that it happened during the Easter season is even more profound.

As Pilgrims of Hope, we had a front-row seat for God’s providence in continuing to care for His sheep by providing another shepherd to lead us in Pope Leo XIV. It reminds us that while we will all die, we have the chance to be resurrected in Christ, and seeing that corporal in Orvieto solidified the reality of Jesus being with us through the doubts and mourning of the present age; and more practically, the reality that He is present to us every time we meet Him in Mass. If that doesn’t fill us with hope, what will?

Assisi

As hundreds of thousands descended on St. Peter’s Square for Pope Francis’s funeral Mass, our group walked to the Basilica of St. Clare in Assisi, where we gathered in front of a massive screen livecasting the funeral. Among hundreds of other Catholics–some local, others from untold corners of the world–we sat in the morning sun, with the breeze in our faces and the smells of Spring filling our noses. We assembled on small chairs and sat around the fountain, basking in the beauty of God’s creation and paying our respects to Pope Francis in the town of Saint Francis, from whom he chose his papal name.

Departing from the funeral, we walked a short distance to venerate Blessed Carlo Acutis: a soon-to-be Saint who truly understood the power of the Eucharist. Are you sensing a theme?

The dedication and excitement surrounding Blessed Carlo’s canonization are tremendous. People of all demographics and cultural backgrounds are drawn to him. Seeing small children, their parents, and grandparents wearing shirts with his face on them speaks volumes.

The line to see Blessed Carlo was about 30-45 minutes long. However, what was most noticeable were the crowds on the streets of Assisi. People were everywhere because of the Pope, Blessed Carlo, and most of all, Our Lord’s continual grace through the Eucharist.

Rome

When we arrived in Rome, the crowds grew. Entrance lines to the major basilicas were long, but moved quickly. Having timed entries as a group gave us an advantage in line, and we saw all the places we planned to see, with the obvious exception of the Canonization Mass. 

I have been blessed to travel twice this year to Rome. When I was there in January, the crowds were minimal. Now, at the apex of the Jubilee year, they are anything but.

Preparing for Crowds

The volume of pilgrims in Italy during the Jubilee is impressive, but even more impressive is how well everyone seems to be prepared. We were in Assisi and then Rome at what may be the high-water mark of the Jubilee year. Yet services were available, and the lines, while longer than usual, moved well in most places. That being said, there are some things that you should prepare for when traveling to Italy this year.

Restrooms

Restrooms in Italy are always scarce compared to the USA, and the lines to access them during the Jubilee can be long. Be prepared to wait. Additionally, things like toilet paper tend to run out quickly, so have a little bit in your purse or bag, and always carry hand sanitizer when soap or a sink is unavailable.

Pickpockets

As you might imagine, pickpockets are having a field day with the larger-than-usual crowds. So be aware. Here are a couple of things to watch out for:

• If anyone you don’t know stops you, hold your items closely. It is common practice for someone to distract you while another picks your pockets.
• It’s summer in Italy. Be cautious of anyone carrying a sweater or jacket draped over their arm. Pickpockets often use this to hide their sleight of hand.
• NEVER…seriously NEVER carry your items on your back in a crowd. And never drape your purse or backpack over your seatback. Put your backpack in front of you or wear a cross-body bag that you can hold in front of you. Keep your eyes on your valuables at all times in crowds.
• Don’t carry too much cash or important documents. Use the hotel safe and only carry what you need each day.
• Leave important and expensive jewelry at home. Opt for Timex over Rolex and let someone watch over grandma’s pearls while you travel.
• Make sure to photocopy passports and credit cards (front and back) and leave a copy with a trusted friend at home and another in the hotel safe. That way, you have all the information in case one goes missing.
• Finally, if you are pickpocketed, let your guide or tour manager know immediately.

Standing and Walking

Due to the crowds, buses cannot get as close to many sites as they usually can, which means additional walking. Also, traffic is heavier than usual, so buses can sometimes be delayed picking up the group. We have mentioned the lines, but remember that you will be on your feet there too. Be prepared to walk more and stand more on your Jubilee Year pilgrimage.

Be Mindful of Time and Group Movement

When you are traveling with a group, everyone has a different relationship with time. Many are early, most are punctual, and some are always late. Please do your best to be early. Our groups have timed entries for the Masses and Holy Doors. That means less waiting in line, but it also means that we have to be there on time. If you are late to the bus or if you get lost because the group moved on while you weren’t paying attention, it can affect the entire group. Here are a few pointers to help you stay on time:

• If you cannot hear the Tour Manager or Guide on the whisper set, you’re too far away from the group; move closer.
• If the bus is leaving at 2:30, plan on being there at 2:15.
• Double the time you estimate for anything requiring service, such as meals on your own or shopping. Larger crowds, European service times, and staff limitations mean things generally take longer in Italy. This is even more prevalent during the Jubilee. Plan accordingly.
• If you are having trouble keeping pace with the group, start at the front. If needed, speak with the Tour Manager or Guide about meeting the group at the next location.

Tipping

Let’s just get this out of the way now. YES, people expect tips in Italy. I’m sure that your brother’s second cousin said they don’t, but they do. They don’t expect the lavish tips we generally give in the USA, but they do expect something, especially from American travelers.

Plan on tipping in restaurants, local guides, hotel cleaning staff, and porters. We do our best to help with this by collecting tips from you early in the trip that your Tour Manager uses along the way for you. Be sure to give your tip envelopes (in your documents package) to the Leader upon arrival, so everyone is tipped appropriately and you can focus on your pilgrimage rather than concerning yourself with who to tip when and how much.

In Conclusion

Traveling to Italy this Jubilee Year is a momentous experience. It is an exciting time to be a Catholic, and having the opportunity to visit the seat of the Church on Earth is an opportunity that no Christian should let slip by.

If you have been on the fence about going to Italy for the Jubilee, I encourage you to go! The largest crowds are most likely behind us, and the graces of pilgrimage are plentiful and waiting for you in Italy. Go and attend one of the first Wednesday audiences with Pope Leo XIV. Go and receive the indulgence available for walking through the Holy Doors. Go and meet a few new (to you) saints and even a few who will be saints soon. Go and show the watching world that the Catholic Church is built to last and that Jesus’ real presence continues to change lives.

In short, go on a pilgrimage!