Hacking Italy's Jubilee

Planning a European pilgrimage in 2025 with five kids, 100 degree heat, and zero packing skills will be the hardest part of the journey.

The last time I went on a trip to Europe I booked a hotel (for two), bought our tickets (for two), and we had a great time. I did almost zero research ahead of time and everything was great.

This year will be a little different.

I used to live in Europe. I spent years traveling through Europe in the summers, working, and going to school there on semesters abroad. My mother moved to Paris when I was in college and I lived with her for a while. I had a job, a commute, an entire life in Europe. In other words, a jaunt across the pond with the fam should be a breeze.

But I have never been abroad with five children—and certainly not during a Jubilee year (more about that later). But this summer we will embark on a European excursion that is part pilgrimage, part family reunion.

In the old days, to plan a family trip abroad you just sauntered into the local travel agency and asked them to sign you up for a flight, a hotel, and a nice tour guide who would handle the details. You arrived at your destination, looked around, went home.

If you were a high school student in the 90s, you packed a backpack, bought a Eurail pass and a Let’s Go: Europe guidebook, ate cheap and stayed in hostels. Greece on $20 a day? No problemo, and you’ll have the time of your life.

My first bible.

Once, on a summer high school trip with a few classmates, we took the ferry from Samos to Turkey. My best friend somehow dropped her passport overboard into the Aegean just as we were docking. A very kind Turkish man standing on the dock saw this happen and dove into the water, dressed in a suit, to retrieve it for her. He handed it to her soaking wet and then got mad when we tried to pay him for his trouble.

Simpler times.

This year we have a can’t-miss family event in Italy, and so there is no turning back, despite all the Jubilee warnings. The plan is to spend a few days in Rome and the rest on the coast. What could be so hard?

Well, 2025 in Italy is a once-every-25 year event that draws Catholic pilgrims from around the world. 30 million visitors are expected, and I expect all 30 million will be in front of us in line at every women’s bathroom we encounter.

Meet the Travel Hackers

When planning a big trip in 2025, prepare to lock in. You may in fact need to clock in. Cancel your weekend plans and settle in.

You will quickly realize you haven’t even begun to think about packing and you have already failed at travel.

They planned their trip poorly and got sent to Rick Steves jail.

An idle Google search of how to do a few tourist activities in a popular location will uncover a perilous landmine of obstacles.

But don’t worry! Armed with the right knowledge and clever travel hacks gleaned from thousands of hours of study, you just might be able to avoid these!