Wherever We May Roam - Travels With Jim and Rita

Jim Santos, travel writer and his wife, Rita
  • 5.0 (1)
  • Places & Travel
  • Updated Weekly

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.

  1. 2 days ago

    Accommodations Can Make Or Break A Trip

    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 apartment with no air conditioning to walking away from a “stinker” in Glasgow, we break down what actually happens when reality doesn’t match the photos.  We share practical travel tips for booking hotels and Airbnbs with fewer surprises: how to read reviews for patterns, why “trusted hosts” can matter, and why sticking with one booking platform can help you get better support, discounts, and smoother problem resolution. We also dig into location research using Google Maps, Google Earth, and Street View, especially when short-term rental apps only show an approximate address. That small step can save you from booking a beautiful place that’s miles from groceries, transit, or anything you need without a car.  We also cover the questions we now ask before we book: elevators, heating and cooling, refund policies, and the hidden fees that can blow up your travel budget. Plus, we talk about cash-only check-ins in places like the Galapagos, ATM limits, and why documenting issues with photos and screenshots right when you arrive can protect you later. Above all, we come back to the travel mindset that keeps trips fun: stay calm, stay flexible, and be willing to pivot when the best move is simply finding a better place.  If you like real-world travel advice that helps you travel longer and travel better, follow the podcast, share this with a friend, and leave a quick review so more people 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 discussed, or would like to be on our show, email us at jim@jimsantosbooks.com. "Wherever We May Roam: Finding Your Travel Style" is available on audiobook on Amazon, Audible, and other audiobook outlets! Subscribe to our Mailing List https://www.buzzsprout.com/2292506/supporters/new http://jimsantos.net https://www.instagram.com/jimsantosblog https://www.youtube.com/@jimsantos508 jim@jimsantosbooks.com "Wherever We May Roam: Finding Your Travel Style" - On Amazon

    23 min

  2. 17 June

    The Schengen Shuffle Without The Panic

    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 departures: many countries require at least six months of validity left on your passport at entry. From there, we zoom out to the bigger question long-term travelers ask again and again: how long can I actually stay? We share examples of countries with longer stays, renewal options, and paid extensions, plus why you should always confirm the latest requirements right before you go since policies change often. Then we tackle the “Schengen shuffle.” We explain what the Schengen Zone is, why it gets confused with the European Union, and how the 90 days in any rolling 180-day period rule really works. The sliding window is the part that trips people up, so we talk through a clear mental model, why tracking by hand is risky, and how Schengen calculator apps can keep your itinerary honest. We also make the case for building buffer days, because a delayed flight or train can turn a tight plan into an overstay with real penalties. Finally, we demystify ETIAS (the European Travel Information and Authorization System): what it is, how it connects to your passport, what it costs, and why it does not extend your time in the Schengen Area. If you’re planning extended travel in Europe, slow travel, or a flexible multi-country itinerary, this is your roadmap to staying compliant without losing the joy of the journey. Subscribe for more practical travel strategy, share this with a friend planning Europe, 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 discussed, or would like to be on our show, email us at jim@jimsantosbooks.com. ETIAS Website: https://etias.com/ "Wherever We May Roam: Finding Your Travel Style" is available on audiobook on Amazon, Audible, and other audiobook outlets! Subscribe to our Mailing List https://www.buzzsprout.com/2292506/supporters/new http://jimsantos.net https://www.instagram.com/jimsantosblog https://www.youtube.com/@jimsantos508 jim@jimsantosbooks.com "Wherever We May Roam: Finding Your Travel Style" - On Amazon

    17 min

  3. 10 June

    How Much Does Long-Term Travel Really Cost?

    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 budgeting framework we use after 16+ years of travel: list your fixed monthly expenses, focus on reliable net income, and build a buffer by spending only about 80% of your available number. Then we get specific about what actually moves the needle. Slow travel often lowers your cost per day with shoulder season pricing and length-of-stay discounts, while constant hopping between cities can quietly raise your spend. We compare real destinations and real outcomes, including months where we stayed near our $3,000 target in places like Mexico and Spain, and the kind of high-cost month you can create when you add frequent moves and a rental car. We also cover the unglamorous stuff that protects your budget: choosing lodging locations that don’t force expensive transport, using buses and public transit, shopping at local markets, and tracking early spending so “small” purchases don’t snowball. We share why we won’t travel without full-trip travel insurance, plus how we use credit card points and airport lounge access to cut airfare and food costs. Finally, we talk booking strategies, how loyalty with platforms can earn discounts, and why documenting an Airbnb problem properly can make all the difference. If you’re planning extended travel, part-time roaming, or even a full-time travel lifestyle, hit play, take notes, and build a plan you can actually sustain. Subscribe, share this with a friend who’s stuck on the budget question, 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 discussed, or would like to be on our show, email us at jim@jimsantosbooks.com. "Wherever We May Roam: Finding Your Travel Style" is available on audiobook on Amazon, Audible, and other audiobook outlets! Subscribe to our Mailing List https://www.buzzsprout.com/2292506/supporters/new http://jimsantos.net https://www.instagram.com/jimsantosblog https://www.youtube.com/@jimsantos508 jim@jimsantosbooks.com "Wherever We May Roam: Finding Your Travel Style" - On Amazon

    25 min

  4. 3 June

    Full Time Roaming - How To Travel Without A Home Base

    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 the unglamorous systems that suddenly matter a lot: mail, physical address requirements, banking and credit cards, renewing a driver’s license, and the limits of virtual mailbox services like PMBs. We also get into the practical side of downsizing, whether it’s worth storing a car, and how eliminating a home base can cut recurring costs while introducing new logistical headaches. Health and comfort matter too. We discuss prescription medication access abroad, why over-the-counter rules vary by country, and how routines make long-term travel sustainable. From choosing walkable neighborhoods to slowing your pace with longer stays, we explain how “slow travel” can feel more like real life and less like a never-ending sprint. We also zoom out to the bigger point: not everyone needs to travel full-time to get what they want from travel. Sometimes part-time roaming or extended getaways offer the best balance, especially when family traditions and a home base still matter. Subscribe, share this with a friend who’s dreaming of long-term 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. 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. "Wherever We May Roam: Finding Your Travel Style" is available on audiobook on Amazon, Audible, and other audiobook outlets! Subscribe to our Mailing List https://www.buzzsprout.com/2292506/supporters/new http://jimsantos.net https://www.instagram.com/jimsantosblog https://www.youtube.com/@jimsantos508 jim@jimsantosbooks.com "Wherever We May Roam: Finding Your Travel Style" - On Amazon

    21 min

  5. 27 May

    The Realities of the Digital Nomad Lifestyle

    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 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 "Wherever We May Roam: Finding Your Travel Style" is available on audiobook on Amazon, Audible, and other audiobook outlets! Subscribe to our Mailing List https://www.buzzsprout.com/2292506/supporters/new http://jimsantos.net https://www.instagram.com/jimsantosblog https://www.youtube.com/@jimsantos508 jim@jimsantosbooks.com "Wherever We May Roam: Finding Your Travel Style" - On Amazon

    20 min

  6. 20 May

    You Can Travel For Months Without Quitting Your Life

    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 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 . "Wherever We May Roam: Finding Your Travel Style" is available on audiobook on Amazon, Audible, and other audiobook outlets! Subscribe to our Mailing List https://www.buzzsprout.com/2292506/supporters/new http://jimsantos.net https://www.instagram.com/jimsantosblog https://www.youtube.com/@jimsantos508 jim@jimsantosbooks.com "Wherever We May Roam: Finding Your Travel Style" - On Amazon

    21 min

  7. 13 May

    Extended Getaway 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 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. Subscribe to our Mailing List https://www.buzzsprout.com/2292506/supporters/new http://jimsantos.net https://www.instagram.com/jimsantosblog https://www.youtube.com/@jimsantos508 jim@jimsantosbooks.com "Wherever We May Roam: Finding Your Travel Style" - On Amazon

    27 min

  8. 6 May

    Wherever We May Roam: A Practical Guide To Longer Travel

    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 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. Subscribe to our Mailing List https://www.buzzsprout.com/2292506/supporters/new http://jimsantos.net https://www.instagram.com/jimsantosblog https://www.youtube.com/@jimsantos508 jim@jimsantosbooks.com "Wherever We May Roam: Finding Your Travel Style" - On Amazon

    21 min
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About

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.

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