Author: Jim Santos
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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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The Scavengers of the Publishing World
As Dennis Miller used to say, “Now I don’t want to go off on a rant here..” – but here I go. A few years ago I wrote a blog post called “Do The Write Thing“, in which I moaned about the difficulties and costs of self-publishing, and how the only people who make any…
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A New Life in San Miguel de Allende
Trading a familiar routine for life abroad sounds dramatic until you hear how normal it can feel when you break it into steps. Chris and Deanna move from the Los Angeles area to San Miguel de Allende, Mexico, after realizing they did not want to look back with regret. Their story speaks to anyone searching…
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Summer Travel Without the Crowds
Planning a summer family vacation can feel like signing up for heat, crowds, and sticker shock. When school lets out, millions of families hit the road at the same time, pushing the same theme parks, beaches, and national parks to their limits. That demand drives up hotel rates, fills restaurants, and turns travel days into…
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Is The Summer Getaway Disappearing?
Memorial Day weekend at Virginia Beach is usually a loud, crowded signal that summer travel season has arrived, but this year it felt strangely quiet. An empty boardwalk and half-closed shops are more than a weather story; they are a snapshot of shifting American travel behavior. When a classic drive-to destination looks subdued, it raises…
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Are Travel Credit Cards Actually Worth It?
A Real-World Look at Points, Perks, and Pitfalls If you’ve spent any time in travel forums or Facebook groups, you’ve heard the pitch: “Just put everything on your points card and you’ll fly business class for free!” It sounds great in theory, but between annual fees, transfer ratios, and vendor surcharges, the math isn’t always…
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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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When the Job Description Doesn’t Include “Prove You’re Still Alive”
Note: Ages and details below current as of July 2026 unless noted. The news that Lindsey Graham has died at 71 is going to generate a lot of tributes this week, and it should — the man spent decades in public life. But if I’m honest, my first reaction wasn’t grief. It was a gut-punch…
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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,…