I’m gearing up for my semi-annual pilgrimage to Italy. We’ll be visiting Rome, Orvieto, Siena, Florence, Monteriggioni, Lucca, and Vernazza. Itineraries are set, flights and hotels booked, bags are packed, and, true to form, I’m preparing myself mentally for every possible thing that could go wrong.

First off, there’s an awful heatwave in Italy that they are calling the Saharan Bubble, which as I understand it is some mythical desert jet stream that will bring record high temperatures to Italy and Europe. Italy is always hot in June, but this heatwave will make things especially scalding. Are there double indulgences if it’s literally hot as hell?

Secondly, being away from my family is always difficult. I’m just so used to sitting around in a pile of kids, so I’m sure the separation anxiety will be spiking at home and abroad. And I’ve got the easier part of that deal!

And then finally, there’s that special sort of stomach flutter when you’re embarking on a sacred journey. This is not a cruise or an all-inclusive relaxation fest. We’ll clock between 20 to 30 thousand steps a day as we visit over 30 churches, give or take, and participate in Siena’s Palio in honor of the Blessed Mother. It will be beautiful, but it will also be grueling.

But there are special graces that go along with a pilgrimage. You know you will encounter difficulties, that’s part of the experience. A good pilgrimage will be ultimately transformative, and transformation doesn’t happen without some discomfort. Pilgrimages force us to encounter the best and the worst in ourselves as our emotional safety nets are stretched, but that creates space in us to experience God in unexpected ways and in unexpected places.

And of course, our particular pilgrimages are analogous to the Big Pilgrimage of Life. We are all on a sacred journey together, helping one another uncover who we are in God and who God is in us.

Pilgrimages remind us of our source, our end, and all those we are connected to along the way. A sign of a good pilgrimage is a growing sense of connectedness with all people and all creation.

But when you’re preparing for pilgrimage, it can be hard. You’ve got to let go to grow, you’ve got to take that single step. You’ve got to trade your comfort and self-reliance for a healthy dose of uncertainty and a whole lot of trust in God. You’ve got to lean into all that remains mysterious and unknown in your soul, to trust in all those wonderful and befuddling mysteries of life.

I’ll be leaning into all that glorious divine mystery next week, hotter than Hell and hopefully, by journey’s end, a little closer to Heaven.

If you’re interested in taking a trip to Italy or attending the Palio in Siena, email me! We take people to beautiful places every year, and we’re already planning a great trip for 2020.