Every Journey Begins Somewhere

Mine began in the U.S. Army

For 43 years, I served my country — 37 as a Soldier and 6 as an Army civilian — and along the way, I traveled the world. But here’s the thing about military travel: you go where you’re sent, when you’re told, for the mission. You see the world, but it’s rarely on your own terms.

When I retired in 2022, that changed. For the first time in nearly four decades, I could go anywhere I wanted, whenever I wanted, for no reason other than the pure joy of it. And I haven’t looked back since.

Meet Buddy

Of course, I don’t travel alone.

Buddy is a small stuffed monkey who goes everywhere with me — and I mean everywhere. He’s sat in airport lounges from Paris to Los Angeles. Perched on the flight decks of commercial airliners and gazed out of the windscreens of Cessnas at 8,000 feet. Watched the sun set over the rooftops of Lisbon, sat quietly in a centuries-old Portuguese church, and charmed locals from Scottish distillery guides to Air France and Delta cabin crew.

He doesn’t talk much. But somehow, everyone loves him.

Buddy started as a good luck charm and travel companion during a deployment to Iraq in 2006, and became something more over time — a symbol of the childlike wonder that travel, at its best, is supposed to give us. No matter how seasoned a traveler you become, there’s always something new to see, someone new to meet, and somewhere new to be surprised by. Buddy reminds me of that every trip.

Who We Travel For

This site isn’t about me. It’s about you.

Specifically, it’s for people who want to travel more — and better — but aren’t sure where to start or how to do it right. Maybe you’re newly retired and ready to finally take those trips you always talked about. Perhaps you’re an infrequent traveler who wants your next vacation to be genuinely great, not just fine. Maybe you’ve always dreamed about international travel but the airport, customs, or the planning process has felt overwhelming.

I’ve been there — or rather, I’ve helped countless people get there. And now I want to help you.

What I Bring to the Table

I’m a retired attorney, which means I pay attention to details, ask the right questions, and give you straight answers. I’m a private pilot, which means I understand aviation from both sides of the cockpit door. As a Delta Million Miler with over 1.5 million miles flown, I know how to navigate airports, airlines, loyalty programs, points and miles, and the ever-changing world of international travel.

I also travel in a suit.

That’s my thing. In another era, people dressed up to fly — it was an occasion, an event, something to be savored. I’ve held onto that tradition not because I judge anyone else’s travel attire (wear what makes you comfortable — truly), but because it’s part of who I am. It’s my way of saying: this matters. This trip matters. Getting on a plane and going somewhere new is not ordinary. It’s a privilege, and I treat it like one.

What You’ll Find Here

At Travel with Buddy and Jordan, we cover the full journey — not just the destination.

You’ll find detailed destination pages covering activities, restaurants, and lodging for places Buddy and I have actually visited. An Aircraft section that helps you understand the plane you’re about to board — because knowing what you’re flying can ease a lot of anxiety. And practical, honest blog posts about navigating airports, clearing customs, using travel rewards, and planning trips that actually go the way you hoped.

And woven through all of it, you’ll find Buddy — sitting on a gate counter at Lisbon Airport, riding England’s LNER train, gazing at the Gulf Coast from a weathered dock in Pensacola, or wearing a Delta captain’s hat somewhere over America.

A Final Word

We travel because we would rather look back on life and say “we did that” instead of “if only we had.”

If you’ve been saying “someday” for too long, let this be the site that helps you turn someday into a date on the calendar. Whether it’s your first international trip or your fiftieth, Buddy and I are here to help you plan it, navigate it, and love every mile of it.

Come join us. The world is waiting.

Jordan (and Buddy)