Category: Life Lessons
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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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Pack Lighter And Travel Easier With Simple Systems
When people picture travel, they imagine iconic sights, not the behind-the-scenes decisions that decide whether a trip feels smooth or stressful. In this conversation, we focus on travel logistics, smart packing strategies, and the practical travel systems that make long-term travel easier. The core idea is simple: travel itself is not complicated, but poor logistics…
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Accommodations Can Make or Break Your Travel
Accommodations are one of the biggest leverage points in travel planning because they affect comfort, budget, safety, and how you spend your time each day. In this episode we unpack why places that look perfect online can still derail a trip once you arrive. A listing can have great photos, strong ratings, and a “perfect…
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A Tale of Two Birthdays
By Jim Santos July 4th, 1976. I was eighteen years old. That number felt significant in ways that aren’t easy to explain to someone who wasn’t there. In addition to being able to buy beer (legally), eighteen meant I could vote for the first time — and there was an election coming in November. It…
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Skip the Airport: How Buses and Trains Make Europe Better (and Cheaper)
By Jim Santos | Wherever We May Roam There’s a moment every traveler knows. You’ve just landed at a new airport, shuffled through passport control, waited at baggage claim, navigated a confusing terminal, and finally emerged into daylight — blinking and slightly dazed — in a city you haven’t actually seen yet. You flew over 600 miles…
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Beat the Summer Rush
Affordable Family Vacations When You Have No Choice But to Go in Peak Season My wife Rita and I have a secret weapon that most families with school-age kids simply don’t have: flexibility. As retired travelers, we’ve learned to love the shoulder seasons — that golden window in April, May, September, and October when prices drop,…
