Category: Europe
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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,…
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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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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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Doing the Schengen Shuffle
Long-term travel gets dramatically easier when you treat visas, entry rules, and passport validity as part of trip design, not last-minute admin. Jim and Rita lay out a simple truth: there is no single “right” travel style, but every style runs into the same border math. Many destinations allow US passport holders to arrive without…
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Europe Travel Tips
Whether you’re a first-timer or a seasoned traveler, these insider tips will save you money, time, and stress on your next European adventure. Planning a trip to Europe is exciting — the architecture, the food, the history, the culture. But between the tourist traps, the overcrowded landmarks, and the hidden fees, even well-traveled adventurers can…
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Wherever We May Roam: Finding Your Travel Style — Now Available
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After years of traveling, learning, adjusting, and sometimes getting it completely wrong, I’m excited to finally share something that has been a long time in the making: My new book, Wherever We May Roam: Finding Your Travel Style, is now available. Why I Wrote This Book Travel has never been a one-size-fits-all experience. Over time, my…
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Castles, Creepy Laundry Rooms, and Airbnb Disasters
Our ten-week journey through Europe recently concluded with an extensive exploration of Ireland, completing a circuit that began on the east coast and took us through Northern Ireland, the Great Atlantic Way, the southern coast, and finally back to the eastern coast of Ireland before finishing in Dublin. After our adventures in England, Wales, Scotland,…
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Exploring Western Ireland: From Galway to the Wild Atlantic Way
Our recent 10-week journey through Ireland’s western coast offered a glimpse into both well-traveled tourist destinations and hidden local gems. After establishing our base in Oranmore, just outside Galway, we set out to experience Ireland’s famous landscapes and small towns that define its rugged western edge. Galway itself presented a mixed experience. As Ireland’s fourth…
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Discovering County Roscommon: Ireland’s Hidden Heartland of History, Legend, and Pastoral Beauty
Escape the crowded tourist trails and discover County Roscommon, a hidden gem in Ireland’s heartland. This beautiful and bucolic county offers a peaceful retreat steeped in history and legend, a place where pastoral landscapes meet ancient stories. While Ireland’s overall visitor numbers have seen fluctuations, with overseas visitors down 15% in March 2025 compared to…