The Story Behind Trip’n With Judy Travel

The Story Behind Trip’n With Judy Travel
A lifelong adventure in the making

As a little girl growing up in a lively family of ten, vacations didn’t mean airplanes or passports. They meant road trips to Ohio, Kentucky, or Michigan to visit relatives. There were no hotel stays or exotic destinations—but there were unforgettable memories: big family dinners, ghost stories whispered into the night by Grandma, and the thrill of sleeping in my very own set of bunk beds at my aunt and uncle’s house. Every trip was wrapped in love, laughter, and the joy of being together.

I didn’t know then that the spirit of adventure was already in me—quiet, patient, and waiting.

At 19, that spirit began to stretch its legs when my dad moved to Denver. My first real vacation followed, and for the first time, I laid eyes on mountains. I remember squinting into the distance and asking, “Are those clouds?” He laughed gently and told me, “No, Judy—those are mountains.” That moment marked something inside me. Wonder. Curiosity. Awe. A hunger for more.

Years later, Alaska stole my heart. I lived there for a decade, and those towering mountains humbled me anew. Alaska wasn't just a place—it was a whole new world. Different languages, different cultures, different rhythms. Living there taught me to take chances, to adapt, and to say yes to life even when it was hard.

That yes led me through joy and loss. When my husband became ill, we moved to Washington to be near his parents. After he passed, I grieved deeply. And when I felt lost, a friend whispered hope: “Go to New York. Reach higher.” So I did.

New York cracked me wide open. It became my second coming-of-age story—this time in a city that never sleeps. Surrounded by dreamers and doers, I found my fire again. I studied, graduated, and when it was time to move on, I chose North Carolina, close to family. Then on a whim? Wyoming. And with it, a revelation: my job with the VA could be my ticket to seeing the country. Every three years, a new post. A new adventure.

And oh, what adventures they were—Utah’s red rock canyons, Washington’s quiet streams, North Dakota’s hushed serenity, California’s wild beauty. Each drive between postings became its own vacation, with every mile reminding me how big and breathtaking this country truly is.

Even retirement couldn’t still my spirit. I took contract work that sent me to Alaska and Hawaii again. Then came COVID. Travel paused. Life shifted. And in the stillness, something sparked: What if I started my own travel business?

And so Trip’n With Judy Travel was born. Named by my grandson (who always knows how to make me smile), it launched during a year when no one was going anywhere—and yet, somehow, it became one of the best years of my life. People were dreaming of travel again. I helped them plan. And when the world opened up, we took off running.

Since then, I’ve led groups through Europe, returned to Alaska four times to share the place I still call home, and will escort a group to Hawaii in 2026. Some trips are solo—just me, the open sky, and the beauty of being still. Others are shared, with friends, family, and guests whose faces light up when they see something new for the first time.

I've helped plan marriage proposals at sea. I've laughed with guests over dinner as they told me how this trip changed them. I’ve watched children dream bigger. I’ve witnessed healing, joy, discovery. Every traveler carries a story—and I get to be part of it.

Travel isn’t just about where you go. It’s about how it changes you. It’s about the little girl who once thought mountains were clouds, growing into a woman who climbs them—again and again.

So come along. There’s a whole world out there still waiting for us. And if you ask me? The journey is just getting started.

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