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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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When our flight touched down in Dublin, we had no idea our carefully planned 29-day Irish adventure would begin with financial shock. Our supposedly bargain $18-per-day rental car suddenly required mandatory insurance at €58 daily plus a €31 fee for crossing to Northern Ireland—ballooning our anticipated $522 cost to nearly $2,500. Welcome to Ireland, indeed!

Belfast greeted us with beautiful architecture at City Hall and Queen's University, but also with sobering reminders of The Troubles at every turn. The hop-on-hop-off tour highlighted bombing sites and memorials rather than typical tourist attractions, creating a somewhat melancholy atmosphere despite interesting spots like the Titanic Museum built near the shipyards where the ill-fated vessel was constructed.

As we ventured along the coast, we discovered that sometimes the most famous attractions aren't the most rewarding. The Giant's Causeway, though geologically fascinating, was overwhelmed with tourists even in early May and bitterly cold with whipping winds. Meanwhile, lesser-known Dunluce Castle offered dramatic clifftop ruins, Game of Thrones connections, and the luxury of space to explore without crowds.

Our counterclockwise journey around the island revealed Ireland's constantly shifting landscapes—from dramatic coastlines to rolling countryside, often changing every few miles. The Wild Atlantic Way provided breathtaking scenery, while small towns offered unexpected treasures. In Donegal, a beautifully preserved 15th-century castle gave us a genuine glimpse into medieval life with its thick stone walls and vaulted wooden ceilings.

Roscommon became our favorite Irish destination, with its fourteen-acre Loughnaneane Park featuring walking trails, wooden sculptures of Gaelic heroes, and castle ruins we could explore freely without entrance fees or formal oversight. Local pubs provided authentic connections with colorful characters, including a bartender who insisted the proper local pronunciation of "Mur-RAY" was actually "Murry," and claimed the other version was "posh."

The most profound aspect of our journey was encountering Ireland's painful history at every turn—castle fortifications built out of necessity, famine memorials in town squares, and exhibits describing the "coffin ships" that transported desperate emigrants to America. At Strokestown's Famine Museum, seeing my family name among those who fled or were forced onto ships hit home in ways I hadn't anticipated.

Despite these echoes of historical trauma, we were consistently moved by the warmth and resilience of the Irish people, their genuine hospitality, and their ability to acknowledge a painful past while embracing visitors with open arms. Our Irish adventure reminded us that travel isn't just about seeing beautiful places—it's about understanding the complex human stories that shape them.

For information on the 2025 International Living Ultimate Go Overseas Bootcamp in Portland, Oregon August 29th-September 1st : https://www.internationalliving.com/events

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Ever wondered what happens if you need serious medical care while traveling abroad? When Jim's shoulder began failing him in Ecuador, he faced a critical decision that many Americans contemplating life overseas worry about – should he return to the familiar but expensive US healthcare system, or trust foreign doctors with his surgery?

Jim takes us through his remarkable journey from initial diagnosis to complete recovery after undergoing shoulder surgery in Ecuador. The contrast with his previous experience in the American healthcare system is striking – instead of waiting four months for insurance approvals and scheduled procedures, his entire process from consultation to operating room took just 15 days. Even more surprising was the final bill: $6,200 total compared to $16,000 for similar treatment in the US.

Beyond the financial aspects, Jim reveals the philosophical differences that make healthcare abroad so different. In Ecuador, patients maintain their own medical records, pharmacists return prescriptions for future use, and doctors spend significant time discussing lifestyle factors affecting health rather than just treating symptoms. The system places much more personal responsibility on patients while creating more human connections – from doctors making house calls to hospitals accommodating family members who stay overnight with patients.

Drawing from his audiobook "Living Abroad: Challenging the Myths of Expat Life," Jim addresses common concerns about quality of care, insurance options, and whether medical tourism makes sense for everyone. His balanced perspective acknowledges both the benefits and potential drawbacks, providing valuable insights for anyone considering healthcare options beyond American borders.

What healthcare stories have you experienced while traveling? Have you ever considered seeking medical treatment abroad? Share your thoughts or questions and join our growing community of global travelers seeking authentic experiences worldwide.

For information on the 2025 International Living Ultimate Go Overseas Bootcamp in Portland, Oregon August 29th-September 1st : https://www.internationalliving.com/events

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