Wherever We May Roam - Travels With Jim and Rita
Not all travel is created equal. Some people take a two-week vacation and call it an adventure. Others disappear for months—or years—without ever really “coming home.” We discuss the challenges, rewards, and drawbacks of travel both domestically and overseas. Information for the would-be expat, digital nomad, roving retiree, or just plain traveler. We can help you find the travel style that is right for you. But this isn’t just theory. Drawing on over 16 years of real-world experience, Jim and Rita Santos share practical, honest advice on what it actually takes to travel longer, smarter, and with fewer surprises. Host Jim Santos is a published travel writer with over 200 articles and eight books (jimsantos.net). He and his wife Rita lived in Ecuador for 6 years, and have tried every style of travel - including selling their home at one point to travel full-time. They and are currently enjoying the roving retirement lifestyle, taking trips of 2-3 months and returning to their home base to visit family and friends.
Episodes
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-trip win...
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...
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 mindset behind...
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 digital nomad at 22, and why mo...
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: we hand AI ...
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 heavily, why Amex Gold can be...
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 psychology, Jewel brings a teacher’s ey...
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 opened their eyes t...
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 choosing places t...
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 financial stress.
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. We talk abo...
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 styles we&rsqu...
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 for every scenario, why complic...
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 apartment with no ai...
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 departures: many c...
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 budgeting f...
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 the unglamor...
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.
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: ex...
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 tr...
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