Wherever We May Roam - Travels With Jim and Rita

Send us Fan Mail Life doesn’t follow a map, and neither do the journeys that shape us. We’re joined by Shannon Lamkin, author, speaker, and host of the internationally listened to podcast Travel Time Stories with Shannon, for a conversation that starts with travel and quickly gets more honest. Shannon shares how a show built around destinations evolved into a space where people tell the stories th...

Send us Fan Mail You can’t “budget” your way to a better trip if you don’t know where the money leaks actually happen. We sit down with Australia-based author, travel writer, and travel coach Linda King to unpack a practical approach to budget travel that feels empowering, not restrictive: save with intention so you can travel more often and for longer stretches. We get tactical on the big pre-tri...

Send us Fan Mail You can live overseas for years and still feel your stomach drop the first time you travel alone. That tension between “I want to go” and “what if I can’t handle it” drives our conversation with Paula Barnes, the travel creator and expat storyteller behind Truly Expat Travel, joining us from Sydney. Paula shares how a “six-month” move from Australia turned into nearly two decades...

Send us Fan Mail You can spend a fortune on a “once-in-a-lifetime” family vacation and still come home thinking, we barely connected. That’s why we sat down with Paul Partridge, a former financial advisor and retirement planner who now designs multigenerational trips as a different kind of investment: time together that turns into stories your family repeats for years. Paul shares the planning min...

Send us Fan Mail Travel technology is changing so fast that it can feel like you need a new degree just to book a flight. We sit down with Madison Rolley, a travel content creator and entrepreneur with a tech background, to bridge that gap and make modern trip planning feel simple, practical, and worth your time. Madison shares how studying abroad sparked her travel confidence, how she became a di...

Send us Fan Mail Weeks of travel planning can come down to one stubborn problem: turning a big dream into a realistic route that fits your time, energy, budget, and check-in times. We’re Jim and Rita Santos, and we’ve built plenty of complicated itineraries the old-fashioned way with spreadsheets, tabs, and too many “wait, what day do we check out?” mistakes. This time, we try something different:...

Send us Fan Mail That $895 annual fee can either buy you real travel freedom or it can quietly drain your budget while you chase perks you never use. We put premium travel credit cards under a practical microscope and share what happens when you treat points like a tool instead of a hobby. We walk through the exact cards we carry and why: what Amex Platinum is good for when you’re traveling heavil...

Send us Fan Mail Saying yes to the kind of trip that makes your stomach flutter can be the start of a brand-new life. We sit down with Jewel Rozanski, a former public high school Spanish teacher who turned her passion for educational travel into Cultured Travel, creating immersive small-group tours built around history, culture, and real human connection. With a background in educational psycholog...

Send us Fan Mail They sold their starter home, got rid of nearly everything, and pointed their lives toward Mexico with a dog and a whole lot of unknowns. Chris and Deanna Hahn join us from San Miguel de Allende just one month after making the move from the Los Angeles area, and they share what the jump actually feels like when the spreadsheets end and real life begins.    We talk about what first...

Send us Fan Mail Summer travel can turn into a perfect storm: packed parking lots, brutal heat, inflated hotel prices, and kids melting down in line. We’ve lived it, and we also know it doesn’t have to be that way. Jim and Rita Santos share a smarter way to plan a family summer vacation when your only time off matches everyone else’s: stop chasing the most famous spots at the worst time, and start...

Send us Fan Mail Memorial Day weekend at Virginia Beach is supposed to be packed, so when we stepped onto a nearly empty beach and a quiet boardwalk, we knew it wasn’t just the rain. We’re Jim and Rita Santos, and we use this familiar trip as a real-time signal that something bigger is shifting in American travel, especially for middle-class families trying to plan a simple vacation without financ...

Send us Fan Mail The hardest part of planning a long international trip right now isn’t choosing the destination. It’s deciding what to do when the world won’t sit still. Visa requirements change without warning, flight routes get shuffled, prices climb, and the news cycle makes every corner of the map feel uncertain. We walk you through how we plan months-long travel without spiraling into fear....

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...