From the Highlands to Tuscany… 🥃🍷
words never suffice

How do you possibly describe ten days with a group of kindred spirits, new friends and old, as you trek through stunning Scotland? You don’t, really… because from my experience in doing these trips (seven of them now!), words never suffice. You try your darndest to capture what it’s like to share the experience of attending the Highland Games in a miniscule village on castle grounds (a castle featured in Downton Abbey, no less), witnessing the otherworldly beauty of the Isle of Skye, wandering the streets of Inverness at dusk with friends who feel like family, and standing in the crypt of an old church from the EIGHT hundreds (as in, the ninth century 🤯)… and it’s just too hard to describe.
As always, it’s always the people. Those who join us as we trek through these hallowed, historic territories are easily the best part of each of the experiences we’ve had, and I can’t begin to express my gratitude for these folks who entrust Kyle and me with our sacred ten-ish days together. What a gift.
And since words never suffice, photos will have to do.
Summer 2027’s Pilgrimage… 🍷
Care to join us next summer? I’m thrilled to finally announce our next location: the Tuscan region of Italy, from June 14-24, 2027!
This is the first time I’ll repeat a location, but with good reason: it’s one that so many of you request, time and time again, and it’s quite probably my favorite spot on earth (second to the four walls inside my own home).
Everything in Tuscany is art—from the literal art, yes, but also the food (oh, the food!), the wine, the farming, the artisanal handmade goods, the lay of the land, the slower pace of life… Even the air smells sweeter here, a mysterious concoction of jasmine, cypress, and the history witnessed by countless cobblestoned piazzas.
—Oh, and let me take you to my favorite gelato place. You’ll never be the same.
Our family’s priest, Fr. Patrick McCain, will be joining us as our spiritual guide, and he himself lived in Rome for four years during seminary. …He’ll give us his behind-the-scenes input on best spots for pasta, coffee, wine, adoration, and more. And of course, celebrate daily Mass with us.
I have so many fond memories from this slice of the world…. It’s one of the few places I’ve visited where I could genuinely live (believe me, I’ve researched the cost of those forgotten Italian villages in need of a little lot of TLC). …And I’ve been to quite a few places.
Please let me show you Tuscany. I’d love to spend time with you there.
Heads up that as of today, there are already seven people registered (!), and I haven’t even promoted this trip yet. Space is limited, and I have a suspicion this one will fill up fast. We experience so much for the price… I promise it’s worth every penny.
I hope you’ll join us!
xoxo,
Tsh (and Kyle)



















