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The digital nomad lifestyle looks effortless from the outside, but the moment you try to earn a living while crossing borders, you find out you are juggling two demanding worlds at once. We talk through the difference between “traveling” and “working while traveling” and why that gap is where most people get tripped up, especially when time zones, deadlines, and constant change collide.

We define what being a digital nomad actually means, why remote work exploded after COVID, and how many Americans now work on the move, both inside the US and internationally. From our own experiences working on the road, we get into the unglamorous details that make or break location-independent work: stable routines, reliable internet access, backup plans for power and connectivity, and why moving too fast can turn the dream into nonstop problem-solving.

We also dig into the practical travel planning issues people avoid until they hurt: visa rules that shift by country, longer-stay options, digital nomad visas, tax questions, and what you generally cannot do without proper permits. Then we cover the human realities, including freelancing income swings, loneliness when you cannot build community, career limits from remote-worker bias, and healthcare decisions that follow you back to the United States, including Medicare timing and penalties.

If you enjoyed this episode, be sure to follow the podcast, and if you have a moment, leave a quick review. It really helps more people find us. And if you want to go deeper, you can check out my book, Wherever We May Roam, Finding Your Travel Style, where I walk through all of this in more detail. You can search for it on Amazon in Kindle, paperback, and audiobook, or just use the link on our podcast page. If you have any questions, a topic you would like discussed, or would like to be on our show, email us at jim@jimsantosbooks.com

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You don’t have to blow up your life to travel longer you just have to travel differently. We’re Jim and Rita, and we’ve learned that the real breakthrough isn’t a bigger bucket list. It’s choosing a travel style that fits your real-world responsibilities while still giving you the time to go deeper than a quick getaway.

We dig into the “part-time roamer” lifestyle: extended travel for one to three months at a time while keeping a home base. That single choice changes your pace, your budget, and your mindset. Instead of rushing from attraction to attraction, you start living like a temporary resident finding the local market, figuring out public transportation, and building simple routines that make a new place feel familiar. We share what that looked like for us across long stays in Panama and Mexico, including why some locations felt like a perfect cultural fit and why others didn’t.

You’ll also hear the less-glamorous side of long-term travel planning: finding the right accommodations, dealing with heat waves and broken air conditioners, and handling the logistics back home like car storage, home temperature, lawn care, and the surprisingly tricky mail question. We compare slow travel with a version of fast travel that still feels relaxed, and explain why trains and buses often beat airports for stress, cost, and actually seeing the country.

We close with the difference between part-time roaming and “part-time expat” life, plus why having a home base can be the best of both worlds especially when travel throws you a curveball. If this sparked ideas for your own extended travel plans, follow the podcast, leave a quick review, and share this with a friend who’s dreaming about traveling longer.

And if you want to go deeper, you can check out my book, "Wherever We May Roam, Finding Your Travel Style", where I walk through all of this in more detail. You can search for it on Amazon in Kindle, paperback, and audiobook, or just use the link on our podcast page. If you have any questions, a topic you would like discuss, or would like to be on our show, email us at jim@jimsantosbooks.com .

Congrats to 100 Goodreads users who won free copies of "Wherever We May Roam: Finding Your Travel Style". If you didn't win, click here to order your copy!

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Your vacation shouldn’t leave you more tired than your job. We dig into why so many trips feel rushed even when you “did everything right,” and the answer isn’t hustling harder or planning tighter. It’s choosing a different travel style. We call it the Extended Getaway: a three to six week trip designed to be realistic, affordable, and actually restorative.

We walk through the tradeoffs that make short vacations stressful: losing days to airports and check-ins, living out of a suitcase, and trying to cram too many destinations into a tiny window. We also share why we’re cautious about packaged tours, including a story where a simple day trip turned into hours of waiting and barely any time in the place we came to see. From there, we shift to what works better: fewer bases, more flexibility, and a rhythm that leaves room for culture instead of just landmarks.

To make it concrete, we tell the story of our first extended getaway in Italy, from renting an apartment in Florence to the kind of unplanned night in Venice you never could have scheduled. Then we break down a month in Panama City, Panama with real budget travel numbers: a condo with a kitchen, laundry, and a view for under $1,200, cheap rideshares, local mercados, and an average spend of about $100 a day for everything. Along the way we share practical long vacation planning tips like “zero days,” packing light, and building in adjustment time so the trip feels livable.

Subscribe for more travel style guidance, share this with a friend who always overpacks the itinerary, and if the extended getaway sounds like your kind of slow travel, leave us a review and tell us where you’d spend your first three to six weeks.

And if you want to go deeper, you can check out my book, "Wherever We May Roam, Finding Your Travel Style", where I walk through all of this in more detail. You can search for it on Amazon in Kindle, Paperback, and Audiobook, or just use the link on our podcast page. If you have any questions, a topic you would like discussed, or would like to be on our show, email us at jim@jimsantosbooks.com.

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Most travel advice starts with destinations, but that’s not what makes a trip work, especially when you’re traveling for weeks or months. We’re Jim and Rita Santos, and after 16 years of everything from short trips to living abroad and experimenting with full-time roaming, we’ve learned the hard truth: long-term travel doesn’t fall apart because you “did it wrong.” It falls apart when you copy someone else’s travel lifestyle instead of building a travel style that fits your time, budget, and personality.

We’re back for a new season with a new name, Wherever We May Roam, along with our book Wherever We May Roam: Finding Your Travel Style. We break down four common long-term travel styles: extended getaways, part-time roaming, digital nomad life, and full-time roaming. We also unpack the biggest mistake travelers make, planning one style of trip with another style’s rules, and how a simple self-assessment can save you money, stress, and disappointment.

From there we get practical: how cash and payments work overseas now, what to do when accommodations go sideways, how visa rules and Schengen limits can surprise you, and why apps, travel insurance, and a flexible mindset matter more the longer you stay out. We share real stories, from unexpected delays to health care abroad, plus small cost-saving habits that make extended travel more sustainable.

Follow the podcast, share this with a friend who’s dreaming of longer travel, and leave a quick review so more travelers can find us.

And if you want to go deeper, you can check out my book, Wherever We May Roam, Finding Your Travel Style, where I walk through all of this in more detail. You can search for it on Amazon in Kindle, Paperback, and Audiobook, or just use the link on our podcast page.
If you have any questions, a topic you would like discuss, or would like to be on our show, email us at Jim at Jim@SantosBooks.com.

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A medical detour changed our itinerary, but it sharpened our belief in slow travel and why roaming creates better stories than any checklist. We close out season two by sharing a vivid sneak peek of our upcoming book on how to plan, budget, and savor longer stays without tour buses dictating your day. From an apartment steps from the Arno in Florence to a trust-the-chef feast in a tucked-away Venetian trattoria, we relive the small choices that turned into big memories—and the practical systems that made them affordable.

We walk through the core pillars of slow travel: choosing one meaningful focus per day, renting apartments with kitchens to cut costs and live like a local, and using trains and ferries to keep plans flexible. You’ll hear how a wrong turn near Livorno became a Mediterranean moment, why a spontaneous side trip to Lucca beat a packed itinerary, and how rain in Rome turned into a playful, poncho-clad wander across cathedrals, fountains, and welcoming neighborhood bars. We also tackle safety myths with grounded advice, from reading a city’s rhythm to staying present and letting common sense do more work than a lanyard ever could.

We’re taking a short break to finish the book and regroup for future travels, and we’d love your questions and stories as we write. Subscribe, share with a friend who wants more from their trips, and leave a review to help fellow travelers find the show.

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Our journey continues as we embrace "Plan B" - establishing a home base in Tennessee while still spending six to nine months a year abroad. This episode picks up our 10-week European adventure as we complete our circuit around Ireland, revealing both the magic and mishaps of extended travel.

From our stay in a rustic farmhouse near New Ross (complete with a creepy dirt-floor laundry shed) to exploring magnificent Kilkenny Castle with its vaulted long hall, every stop brought new discoveries. We wandered through charming pedestrian "slips" that resembled something from Harry Potter, witnessed dramatic coastlines at Hook Head Lighthouse, and encountered more swans than we could count in the seaside town of Bray.

The journey wasn't without its challenges, particularly when our carefully selected Dublin Airbnb turned out to be an unauthorized rental, leaving us stranded on the front steps with our luggage. This forced us to pivot to a hotel at twice the price - just one example of how travel requires flexibility and a sense of humor.

Dublin itself rewarded us with treasures like Trinity College's magnificent campus, the ancient Book of Kells (though seeing just a single page was somewhat anticlimactic), and the historic Dublin Castle. We even found time to enjoy a proper Irish meal of bacon and cabbage while avoiding the tourist-trap prices of Temple Bar.

As we reflect on our entire journey through Portugal, Spain, England, Scotland, Northern Ireland, Ireland, and Wales, we're reminded why we choose this lifestyle: "We travel not to escape life, but so that life does not escape us." Join us as we regroup at home base before planning our next adventure!

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The wild western coast of Ireland beckons with its dramatic cliffs, winding mountain roads, and villages where Gaelic still echoes through local pubs. Our adventure through this stunning landscape reveals both the tourist-filled hotspots and the authentic gems that make Ireland truly special.

Setting off from our base in Oranmore near Galway, we discover that sometimes the most celebrated destinations don't quite match expectations. Galway's Latin Quarter bustles with tourists but lacks the authentic charm we find in smaller towns. Meanwhile, the Cliffs of Moher deliver their promised drama—especially when viewed from the water—giving us a fresh perspective on these famous "Cliffs of Insanity" from The Princess Bride.

Nothing prepares us for the white-knuckle drive over Conor Pass on the Dingle Peninsula—a road so narrow that two-way traffic must negotiate with a rock wall on one side and a sheer drop on the other. Yet the panoramic views from the top make every tense moment worthwhile, revealing lake-dotted valleys and the expansive Dingle Bay beyond.

The true magic of western Ireland emerges in places like Kenmare, where we sit outside pubs surrounded by locals speaking Gaelic, and in Killarney National Park, where Muckross House and its magnificent grounds offer history and natural beauty without the crowds. We learn that Blarney Castle's famous stone might draw tourists, but it's the surrounding gardens that truly captivate.

Our most memorable discoveries often come unexpectedly—the massive St. Coleman's Cathedral in Cobh with its 300-foot spire, the remarkably preserved Charles Fort near Kinsale, and small seaside villages where authentic Irish life continues untouched by tourism's influence. These moments remind us that travel's greatest rewards often lie just beyond the well-trodden path.

Join us as we navigate Ireland's challenging roads, discover hidden treasures, and find that the heart of Irish culture beats strongest in its smallest towns. Whether you're planning your own Irish adventure or simply dreaming of emerald landscapes, our journey offers both practical insights and the inspiration to explore beyond the ordinary.

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Ever been more terrified of speaking in public than jumping out of a plane? You're not alone. Public speaking consistently ranks higher than death in surveys about our greatest fears, and as my wife Rita and I launch the second season of our travel adventures, I'm facing down this fear once again.

As I prepare for three speaking engagements at the International Living Conference in Portland, that familiar anxiety creeps in. Despite having presented countless times before, my nervousness will build until that moment I step on stage. To illustrate this universal fear, I share the story of my most terrifying public performance – a live TV appearance where I nearly fled the studio. The fascinating disconnect between my internal panic and what viewers actually saw speaks volumes about how we perceive our own performance versus reality.

This tension between comfort and growth applies equally to travel and public speaking. Both require stepping into uncertainty, facing vulnerability, and trusting that we'll emerge stronger. Whether navigating foreign streets or facing an audience, the discomfort precedes the reward. That's why we continue pursuing both challenges despite the fear – because we travel not to escape life, but so that life doesn't escape us.

Join us as our adventure continues, now with a slightly different rhythm but the same spirit of exploration that launched our journey. Connect with us on Instagram, YouTube, or jimsantosbooks.com to follow along, and check the show notes for information about streaming the International Living Conference if you'd like to learn more about overseas living.

Portland Conference: https://www.internationalliving.com/events

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