That Passport Life with Kevin McCullough

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A Note from That KEVIN - 09/26/25

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Friends,

What a week it has been. The rhythms of September always feel like a sprint—kids back in school, work hitting full stride, travel stories stacking up—but this week somehow carried even more weight, more joy, and more milestones than most.

We carved out one of my favorite fall traditions: apple picking with the family (see the story we’ve included). There’s just something about being out in the orchard under crisp skies, filling bags with Cortland and Empire apples, that slows time down and makes life feel exactly as it should. My 15-year-old seems determined to taste test every variety in existence, while the rest of us head straight toward cider donuts and stone-oven pizza at the barn afterward. These little escapes remind me why travel—whether it’s a plane ticket overseas or a one-hour drive into the countryside—isn’t about distance, but about discovery and memory-making.

Speaking of discovery, I could not be prouder to announce the launch of CestSiBon.org. This one is close to my heart because the editor is none other than my bride. Many of you trust me to share the best of travel. Well, what I do for travel, she will do—and likely outdo me—for food. Her new publication is a celebration of flavor, culture, and culinary story, and I want every single That Passport Life subscriber to add C’est Si Bon to your regular reading list. Trust me, you will be inspired, and your dinner table will thank you. And if you want to go deeper, make sure to catch last week’s Wednesday night edition of Radio Night LIVE—my interview with her about the new site is up now, and the podcast replay is available wherever you listen.

Another exciting partnership also took flight this week. I’m delighted to welcome MedJet.com/Kevin to our community. If you’ve followed me for any length of time, you know that I don’t attach my name to anything unless I believe in it fully. I personally used MedJet during our family’s once-in-a-lifetime trip to Italy. They offer the peace of mind that, should something go wrong, you’ll have the medical transport and support you need to travel with true confidence. Sheri Howell from MedJet joined us on radio this week—read and listen to this week’s Travel Tuesday with Linda Perillo for the full conversation.

And speaking of Linda—she’s been out riding horses, Cristyne is jetting off to Paris & St Tropez, and me? Well, I’m finally catching up on the sleep I lost in the whirlwind of early September. It’s been one of those stretches where the calendar never quite keeps pace with the commitments.

These days have also been heavy with grief. I’ve been mourning the loss of my friend Charlie Kirk for two weeks now. Theologian Voddie Baucham also passed last night. I wrote about it at Townhall.com. Grief has a way of sitting in the background of everything you do, even when you keep moving forward.

In the midst of that, I’ve also been blessed with the responsibility of doing major interviews: one with Eric Trump—featured this weekend on the television edition of That KEVIN Show (ThatKEVINShow.com)—and another with Jack Ciattarelli, who hopes to be the next Governor of New Jersey.

It’s a strange thing: to mourn one friend while simultaneously engaging with leaders about the future. But maybe that is the balance of this season—holding grief in one hand and hope in the other.

And there is much hope ahead. This autumn promises milestones worth celebrating, including a new announcement that Linda and I are shaping right now. Next year, we will be leading a bespoke Italian getaway, designed just for you—our That Passport Life community. Imagine walking the cobblestone streets with us, tasting the food, sipping the wine, and soaking in la dolce vita together. Details are coming soon, and I can’t wait to share them.

So yes, it’s been a busy week—an orchard full of apples, a table set with new beginnings, partnerships forged for safer journeys, the sting of grief, and the promise of future adventures. Through it all, I remain grateful: for family, for friends, for each of you who travel this road with me.

All for now. Safe travels!

– KMC

 

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