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Pilgrimages

with Real Life Catholic

Enter to win a FREE pilgrimage to Our Lady of Guadalupe for you and a Friend here!

“A vacation is an escape from life. A pilgrimage is a way to embrace life more fully. Every pilgrimage I’ve ever been on has changed my life for the better, forever. I’m so excited to take you with me.”
— Chris Stefanick

Our Lady of Guadalupe: Mexico City

October 7 - 12, 2025

The Patroness of the Americas, Our Lady of Guadalupe, has been changing hearts since she first appeared to St. Juan Diego in 1531.

Join Chris Stefanick and Jim Wahlberg (yes—that Wahlberg) on this adventure where we’ll visit the Shrine to Our Lady, the largest cathedral in Latin America, and 1500-year-old Mesoamerican pyramids. 

Kauai Pilgrimage to Beauty

April 7 - 12, 2026

Join Chris and Natalie Stefanick on the trip of a lifetime, diving into the beauty of creation where Natalie found God, in one of the most stunning places in the world: Kauai. Experience God revealing himself to YOU through beauty… and a lot of FUN. Daily Mass and reflections, and daily adventures in the mountains and at sea. 10 spots left!!

Catholic Couples Getaway
in Costa Rica

February 6 - 10, 2025

It’s time to unplug from work, step back from the urgent demands of family life…because your marriage deserves it. You deserve it! You need a long weekend away to pour into what you know matters most…a weekend that will renew your marriage, and reignite your faith!

Come away to a luxury hideaway resort in Costa Rica for a life-changing experience with Chris & Natalie Stefanick, Fr. Shawn Monahan, and Mike & Alicia of the Messy Family Project!

Pilgrimage to the Holy Land

June 10 - 19, 2026

Journey with Chris Stefanick on a once-in-a-lifetime pilgrimage to the Holy Land. Experience the Gospels come alive as you pray in the places where Jesus lived, taught, died, and rose again.

Join us in June 2026 for an unforgettable journey of faith, friendship, and transformation. Daily Mass, powerful reflections, and life-changing encounters with the living God in the land where it all began.

This is more than a trip—it’s an invitation to go deeper with Christ.

Holy Land Pilgrimage

December 6 - 15, 2025

The altar in the cave of the annunciation has the words inscribed on it: “the Word was made flesh. Here.” That sums up the Holy Land.

You will touch the place where Jesus was laid in a manger, see the sunrise over the Sea of Galilee, and stand in the empty tomb. You’ll never pray the same. You’ll never be the same. This is the pilgrimage to end all trips. 

I promise to only take you when and if it’s safe enough to take my own children, but when it is, this trip fills up VERY fast.

Assisi Pilgrimage and Retreat

October 5 - 13, 2026

Join Chris Stefanick in 2026 for a powerful pilgrimage to Assisi, marking 800 years since St. Francis’s death.

Journey through the sacred sites where Francis lived, prayed, and received the Stigmata—from Assisi to La Verna and beyond. With reflections from Chris and a Franciscan friar, deepen your faith and renew your call to holiness.

The pilgrimage also includes a Papal Audience with the first American Pope—celebrating both history and the vibrant Church today.

The Holy Land

December 6 - 15, 2025

The altar in the cave of the annunciation has the words inscribed on it: “the Word was made flesh. Here.” That sums up the Holy Land.

You will touch the place where Jesus was laid in a manger, see the sunrise over the Sea of Galilee, and stand in the empty tomb. You’ll never pray the same. You’ll never be the same. This is the pilgrimage to end all trips. 

I promise to only take you when and if it’s safe enough to take my own children, but when it is, this trip fills up VERY fast.

Past Pilgrimages