An Italian trek from Rome through Florence including Subiaco, Assisi, Siena, & more
June 14-24, 2027
Join Tsh & Kyle Oxenreider on pilgrimage through the Tuscan region of Italy
…You'll learn from locals, trod on old soil, witness breathtaking beauty, and spend time together unpacking what you've learned.
This Latin phrase means “the way of beauty,” and its fanciful turn of phrase is probably something you’ve experienced: when the splendor of creativity, be it from God directly or through the work of a human hand, compels you to bow before your Maker and won’t let you go.
You witness it in your daily, ordinary life — now imagine it in one of earth’s most astonishing slices of land: the Tuscan region of Italy, home to history’s best artists and an artistic way of life. From the handcrafted food to the lay of the land to the curve of cobblestone streets, everything here is art. And everything has the potential to point you to eternity. This is the Tuscan way.
“Of all the small nations of this earth, perhaps only the ancient Greeks surpass the Scots in their contribution to mankind.”
– Winston Churchill
A Tidbit of What You’ll Experience:
The four papal basilicas in Rome: St. Paul Outside the Walls, St. Mary Major, St. John Lateran, & St. Peter's
The Vatican: Scavi Tunnels, the Vatican Museum, Sistine Chapel, & a papal audience
Assisi & the Basilica of St. Francis + St. Clare
The last standing Benedictine monastery in Subiaco
Brunello wine tasting in the Val d'Orcia, a UNESCO Heritage Site
The Duomo in St. Catherine's Siena
Michelangelo's David in historic Florence
The literal best gelato in the world (probably several times a day…)
Ample free time to wander in Rome, San Gimignano, Siena, Florence, & more
…and much, much more!
“This was a life-changing, bucket-list trip; Tsh and Kyle’s ability to beautifully marry breathtaking landscapes with meaningful conversations will stay with me all of my days.”
– Annie, a former pilgrim
Who Are You?
You appreciate Kyle & Tsh’s laid-back adventure style of travel—yet whether you're a seasoned nomad or you've never left the country, you're also a little unsure what it might be like to travel with a group of strangers (it's understandable; they were honestly a little unsure what it'd be like to lead a group trip the first time, too!). But rest assured: there are no matching shirts here, and there's no one saying “We’re walking, we’re walking” through a crowd of tourists. When you travel with Kyle and Tsh, you’re joining a like-minded group of pilgrims who value meaningful conversations in meaningful places, who want to savor the big and small pleasures of travel, who are willing to embrace the unexpected, yet who also relish the simple joy of a good conversation over a drink at the café.
You’re flexible and open to participating in a pilgrimage with all walks of life: families with children, young and older pilgrims, men and women, single and married, religious and not (be they Catholic, Protestant, Orthodox, or wherever they are), seasoned travelers and first-time abroad newbies.
So long as you’re willing to learn about yourself, the world, and your place in it—you’ll belong.
Pilgrims from our summer 2022 trip to Italy
Pilgrims from our summer 2023 trip to Ireland
Pilgrims from our summer 2024 trip to Greece & Turkey
Pilgrims from our summer 2025 trip along the Rhine River to the Netherlands, Germany, France, & Switzerland
Meet Your Guides
Kyle and Tsh Oxenreider are explorers down to their bones, and ever since they met on a dirt road in war-torn Kosovo 25-plus years ago, travel has been in their family's DNA. They've lived in Kosovo and Turkey and traveled to well over thirty countries, including having led six group pilgrimages. A decade ago they took their three kids on a round-the- globe journey, spending a school year learning from the greatest textbook there is: the world.
Kyle is a small business owner, and Tsh is a podcaster, teacher and author of six books (with more on the way!), including At Home in the World: Reflections on Belonging While Wandering the Globe. She is also the writer behind the popular newsletter The Commonplace and host of the podcast A Drink With a Friend, both of which explore all of ordinary life through a sacramental lens. Her favorite job title of all time, though, is Mom.
Together, they're experienced travel guides, and both of them are Catholic converts after spending most of their lives as devoted evangelicals and then Anglicans. Their favorite style of travel? Laid-back adventure. When you travel with them, you'll try new things and ask new questions about the world and your place in it, but not at the cost of unwise risk. You'll learn from places and people, then spend time together unpacking what you've learned, usually over a local drink.
Fr. Patrick McCain is a native of Memphis and a convert to Catholicism from his roots as a Southern Baptist. He’s a nerd with a tech and music background who loves Jesus and His Church, and he loves traveling and seeing the world through a Catholic lens. He also loves bourbon and singing karaoke.
He’s the Oxenreiders’ parish priest and served as the spiritual guide and priest for the their pilgrimage along the Rhine River in 2025. They're thrilled to have him join them again!
“My pilgrimage with the Oxenreiders will remain one of the favorite trips of my lifetime. ...I would have paid ten times the amount I paid for the experience I received.”
– Bridget, a former pilgrim
FAQs
What is the group size?
This group will be a maximum of 50 people.
When will group participants be revealed to each other?
You’ll officially meet each other either en route (if you choose group airfare) or at our welcome orientation and dinner the first day. Kyle and Tsh will say hello via email a few weeks before departure.
Will children be on the trip? (Or can I bring mine?)
Possibly! This trip includes a lot of walking, so parents should keep this in mind before signing up their children. If you join us, you are open to learning from fellow pilgrims of all ages, from young adventurers to senior travelers.
Is this trip only for Christians? Or even Catholic Christian-only?
Not at all. Tsh and Kyle are Catholic Christians, and as such, their worldviews are a natural outflow of their faith. Naturally, the conversations throughout the week follow suit.
But as a participant, you’re not asked about your beliefs beforehand, you don’t have to sign some sort of doctrinal statement, and they embrace the idea that God is walking with all of us on a unique journey. One of the features (not a bug!) of their pilgrimages is the eclectic spiritual background of the participants: Catholic, Protestant, Orthodox, or what-have-you.
Will there be chats about the intersection of travel and faith? Yes, absolutely. Will we have (optional) Mass with a Catholic priest who’s joining us as a fellow pilgrim? Yes. Will you have a chance to ask questions about “weird Catholic stuff”? Also yes. But they trust that God knows where you’re at, and there’s no pressure to be anyone but you.
What should I pack?
Layers are key to helping you pack as light as you can. Tuscany is known for its warm summers, and we’ll do what we can to be smart in the heat. Comfortable walking shoes are also a must—we’ll be trekking a lot! You may also want to toss into your bag something simple you enjoy wearing out for the evening. But on the whole, this trip is for ordinary pilgrims, and we highly recommend packing light. Tsh will share her go-to pilgrimage packing list close to departure time.
What's the investment?
The investment for the trip is $4,995 for double occupancy, not including the flight. See the brochure for more details.
Why do the Oxenreiders partner with Select International?
Tsh has led trips on her own before, and they’re a lot of work to plan. As a full-time writer, teacher, and mother, planning a unique trip of this magnitude is often an additional full-time job! Select International has a longstanding track record of excellence in the travel industry (particularly with pilgrimages) and the people behind the scenes are fantastic. Plus, they’re able to make the trip more affordable than if Kyle & Tsh ran it on their own! They’ve loved working with them over the years for their pilgrimages to Italy, Ireland, Greece, and Rhine River, and are thrilled to work with them again.
More questions?
Ask Rebecca Stoker at rebecca@select-intl.com.
“You know how you view an experience from afar and you think, there’s no way that can live up to the hype? The Oxenreider's pilgrimages live up to the hype. It really was that amazing, that thoughtful, that impactful, and that meaningful. You will return with a renewed sense of purpose; fresh air in your lungs. Do whatever it takes to go.”
– Aaron, a former pilgrim
Interested?
Read the brochure for more details or head directly to the page to sign up:
“The world is a book and those who do not travel read only one page.”
– St. Augustine