Category: Slow Travel
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Sailing Through Life
Selling everything to sail around the world sounds romantic until you hear what it actually costs. It isn’t just the money. It’s your identity, your routines, and the comfort of having a backup for everything. In this episode, Rita and I talk with Alison Gieschen and her husband Dan, who traded a successful equestrian life…
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Storytelling and Travel as a Path to Healing
Life doesn’t follow a map, and I think that’s exactly why this conversation stuck with me long after we stopped recording. Rita and I sat down with Shannon Lampkin, a travel storyteller, author, and podcast host who started “Travel Time Stories” as a show about adventure and then watched it turn into something bigger —…
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Travel More for Less
The fastest way to travel more isn’t a bigger paycheck. Believe me, I’ve had a few different paychecks over the years. Some good, some not so much (looking at you, worm farm), and the size of the number was never really the problem. The real trick is having a better system. Travel writer and coach…
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Expat Parenting and Solo Travel
Paula Barnes has been living the expat life for close to two decades now, and if there’s one thing her story proves, it’s that confidence in travel isn’t something you’re born with — you build it, one uncomfortable moment at a time. She and her husband left Australia thinking they’d do six months in Taiwan.…
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A Chat With Madison Rolley
Technology is changing travel planning faster than a lot of us can keep up with. And if you’re a retiree, or just late to this particular party, it can feel like someone handed you a new phone and expected you to already know the passcode. This episode is our attempt to connect the dots between…
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Ultimate AI travel planning that actually saves you time
Planning a long Europe trip sounds romantic, but the reality can be tough. Check-in windows, long transit days, and missed connections add to the challenge. The task of stitching lodging, trains, and buses across many countries also wears you down. With overland travel, we stay in city centers instead of airports. It gives us more…
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How Educational Travel Builds Confidence Through Connection
Saying yes to the trips that scare you a little can reshape your entire life, and that idea sits at the heart of this conversation with Jewel Rozanski, founder of Cultured Travel. After 14 years as a public high school Spanish teacher and training in educational psychology, she turns educational travel into a practical path…
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Travel Smarter in an Uncertain World
Planning a long-term international trip used to feel like a puzzle you could solve once and then relax. Now it can feel like the pieces keep moving: visa requirements shift, flight routes get consolidated, exchange rates jump, and headlines make every destination sound risky. The core skill is not predicting the future. It is building…
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The Reality of Long-Term Travel
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Long-term travel isn’t only about epic sights and bucket-list moments. It’s a lifestyle choice that reshapes your days, your expectations, and your patience. On Wherever We May Roam, we talk through the reality of long-term travel: the rewards, the challenges, and the surprises people rarely plan for. Whether you’re considering an extended getaway, part-time roaming,…
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How AI Turned Days of Trip Planning Into Minutes: A Case Study
By Jim Santos, Wherever We May Roam If you’ve ever tried to plan a multi-country, multi-city overland trip through Europe, you know the drill. You open fifteen browser tabs. You start a spreadsheet. You cross-reference bus schedules against train schedules against “wait, is this city even worth two nights?” And somewhere around city number six,…
