Wherever We May Roam - Travels With Jim and Rita

Send us Fan Mail Long-term travel looks like postcards from the outside, but real life on the road includes fatigue, friction, and the occasional “milk” that turns out to be drinkable yogurt. We’re Jim and Rita Santos, and we share the honest reality of long-term travel: the good, the bad, and the unexpected lessons that only show up after weeks and months away from home. We revisit the travel sty...

Send us Fan Mail Destinations get all the attention, but the real difference between a smooth trip and a stressful one is what happens behind the scenes. We talk through the travel logistics that quietly shape everything, from packing strategy to the phone tools that keep you moving when plans change. We start with the most common travel mistake we see: overpacking. We share how we used to pack fo...

Send us Fan Mail Your lodging isn’t just where you sleep. It sets the tone for your entire trip, your daily schedule, and sometimes even your sense of safety. We’re Jim and Rita Santos, and we’ve learned the hard way that accommodations are one of the easiest parts of travel to get wrong, even when the listing looks perfect and the reviews seem solid. From sweltering nights in a gorgeous Krakow ap...

Send us Fan Mail The fastest way to ruin a great trip is to assume the border rules will “work themselves out.” Jim and Rita Santos unpack the unglamorous but essential side of longer travel: visas, passport validity requirements, and the Schengen Area time limits that surprise even experienced travelers. We start with the basics for US passport holders, including a detail that regularly derails d...

Send us Fan Mail Most people don’t skip long-term travel because they hate adventure, they skip it because the money math feels impossible. We challenge that assumption by showing how travel costs aren’t fixed at all, they’re driven by decisions: where you go, how you move, how long you stay, and whether you travel like a rushed vacation or like a real life on the road. We walk through the simple...

Send us Fan Mail The fantasy of full-time travel is simple: sell the house, grab your bags, and go wherever you want. The reality is both better and messier. We talk through what “full-time roaming” actually means when there’s no reset button, no familiar place to return to, and every move and decision is on you. We share what surprised us most when we tried full-time travel ourselves, including t...

Send us Fan Mail 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 co...

Send us Fan Mail 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...

Send us Fan Mail 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 tra...

Send us Fan Mail 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...

Send us Fan Mail 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...

Send us Fan Mail 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-f...

Send us Fan Mail 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 ce...

Send us Fan Mail 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 Co...

Send us Fan Mail 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 wi...

Send us Fan Mail 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 journ...

Send us Fan Mail Imagine pulling your sailboat into a tiny Greek fishing village where tourists rarely venture, dining at a local taverna where fishermen gather, and experiencing authentic Mediterranean life beyond the postcard views. For travel writer and photographer June Russell-Chamberlain, this freedom to discover hidden gems represents the magic of charter sailing. "The freedom to choos...

Send us Fan Mail What happens when a couple of American retirees tackle the United Kingdom, complete with driving on the "wrong" side of narrow roads, navigating London's famous tube system, and an unexpected series of medical adventures? Join us as we share the highs and lows of our journey through Britain. London welcomed us with its iconic landmarks and efficient public transport...

Send us Fan Mail What would it take to stop you from exploring the world? For Penny Zubula, even total blindness couldn't dampen her wanderlust. This remarkable travel writer navigates foreign countries with her photographer husband Simon and guide dog Splendid—proving that disabilities don't have to limit adventure. Penny's journey from Jerusalem-born, Montreal-raised TV host to ac...

Send us Fan Mail Fifty episodes in, and we're still discovering what retirement travel truly means to us. After a health challenge forced us to pivot from our original three-year international adventure, we've established a new rhythm – a home base in Tennessee with 6-9 months of global exploration annually. Our latest journey began with a two-week exploration of Portugal and Spain that...

Send us Fan Mail Travel writer Linda McCarley joins Jim and Rita to share her remarkable journey from childhood trips to Scotland through her recent decision to purchase a villa in Tuscany. Born in Canada to Scottish parents, Linda's travel adventures began at just three years old, planting seeds for a lifelong passion that would eventually lead her to Italy. With refreshing candor, Linda rev...

Send us Fan Mail Curious about cruise vacations but not sure where to start? Veteran cruiser Babs Dearmond joins us to unpack the fascinating world of cruise travel - from Caribbean beach-hopping to sophisticated global exploration. Babs shares her journey from first-time cruiser seeking winter escape to seasoned traveler who's sailed the Mediterranean, European rivers, and Asian waters. What...

Send us Fan Mail What's driving more and more women to travel solo or join women-only travel groups? This episode dives deep into the transformative power of travel with Sonja Thayer, founder of Rom-Soul Escapes, who specializes in creating women-focused retreats in Italy and Greece. Sonja shares her journey from backpacking through Europe in the 1990s to creating curated travel experiences t...

Send us Fan Mail What happens when you combine a passion for travel, a gift for storytelling, and a heart for helping others overcome their deepest struggles? You get Lori Bruton, our fascinating guest who shares her remarkable journey from trauma to transformation. Lori opens up about the pivotal moments that shaped her path as an author, travel writer, speaker, and breakthrough coach. Her story...

Send us Fan Mail Roy McGinnis and Julie Tallman return to the podcast with exciting news – they've officially committed to building a retirement home in Panama's Azuero Peninsula. After their initial exploratory visit left them enchanted with the rural charm of Petasi, they returned for two weeks to confirm their decision and put down a deposit on property in an expat development. Their...