Wherever We May Roam - Travels With Jim and Rita

Jim Santos, travel writer and his wife, Rita
  • 5.0 (6)
  • 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. 6d ago

    You Can Still Have A Great Trip In Peak Season

    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 choosing places that give you space, shade, and real value. We talk through underrated U.S. destinations that stay enjoyable in peak season, from the Upper Peninsula of Michigan to Maine’s Acadia region, plus quieter stretches of the Carolinas and the less-crowded side of the Smoky Mountains. We also make the case for state parks as the most overlooked summer travel win: cabins or campgrounds, lakes, easy hiking, and activities kids actually love without paying premium prices for stress. Going farther? We explore international summer options built around climate and timing, including northern Portugal and Spain, Costa Rica’s rainy season rhythm, Ecuador’s mild temps and Andes hiking, and the underrated Canada Maritimes. And when Disney World is non-negotiable, we get tactical: what it can really cost, why weekdays matter, how to arrive early, how to avoid the “everyone goes clockwise” trap, and why a midday escape can save your trip. We also flag destinations to avoid in summer when heat, humidity, storms, or crowds turn “uncomfortable” into “miserable.” Subscribe for more practical travel planning, share this with a friend who’s dreading peak season, and leave a quick review so more families can find the show. What’s your favorite summer hidden gem? Companion Blog With Details: https://www.jimsantosbooks.com/wordpress1/2026/06/14/beat-the-summer-rush/ 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

  2. Jul 22

    What If The Summer Getaway Is Disappearing

    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 financial stress.  We break down the economic reality behind the quieter crowds: gas prices that still sting, grocery inflation that rolls straight into restaurant bills, and credit cards that feel maxed out for many households. We also talk about why drive-to beach destinations can be especially vulnerable when budgets tighten, and how a “normal” week away can start to look like a $3,000 decision once food, entertainment, and extras pile on.  Then we zoom out to the political and sociological pressure points that change travel habits even when people still want to get away. From federal job anxiety and military deployments to the post-pandemic revenge travel wave fading, vacation patterns are evolving. Remote work and flexible schedules create more long weekends and fewer big annual trips, while staycations become a practical reset. We share eye-opening examples of today’s family fun costs, from arcades and movie theaters to zoos, aquariums, and theme parks, and what that means for seasonal small businesses that live or die by a short summer window.  If travel feels different for you this year, we want to hear what you’re seeing. Subscribe, share this with a friend who’s budgeting a trip, and leave a quick review so more people can find the show. 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. 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

  3. Jul 15

    Travel Smarter In An Uncertain World

    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. We talk about the perception gap between headlines and what travelers often experience on the ground, why country-wide travel advisories can hide important regional differences, and how we weigh “should we go” decisions using real inputs instead of vibes. We also share specific examples from our own travels, including places we happily revisit and places we avoid when conflict is active. Then we get practical about long-term travel logistics and money. We break down why you should check visa rules directly with embassies, what to watch for with Europe’s ETIAS and EES changes, and how to protect your trip from airline schedule surprises. We cover budgeting for currency swings, when to book flights, and why “cheap” tickets can get expensive fast. Finally, we lay out how we use travel insurance as core infrastructure, including CFAR timing, reimbursement limits, medical evacuation coverage, and the one habit that matters most: reading the exclusions. If you’re planning international travel in 2026, building a flexible itinerary, or trying to travel smarter in an uncertain world, this one will help you leave with a plan and some peace of mind. Follow the podcast, share this with a friend who’s on the fence about traveling, 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.  Compare Insurance Plans: InsureMyTrip.com or Squaremouth.com US State Department https://travel.state.gov/ STEP Program https://travel.state.gov/en/international-travel/travel-advisories/smart-traveler-enrollment-program.html Available on Amazon at https://www.amazon.com/dp/B0H8TBR88L Available as a PDF along with other titles at https://jim-santos-books.square.site/ 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

  4. Jul 8

    The Reality Of Long-Term Travel

    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 styles we’ve been exploring, from an extended getaway to part-time roaming, digital nomad life, and full-time roaming. We also talk about why a home base can still matter even if you love living light, including the practical stuff people forget like licenses, voting, and keeping family traditions steady. Then we get into what slow travel really gives you: freedom to move at your own pace, the ability to stay longer when a place surprises you, and a deeper connection to local culture that rushed vacations rarely deliver. From culture shock in supermarkets to patience when you’re not the priority, we unpack the emotional side of expat life and long trips. We also challenge a common assumption that the United States is automatically best at everything, comparing what we’ve experienced abroad with healthcare, pharmacies, and public transportation. Finally, we talk about reverse culture shock and the biggest mindset shift we’ve learned: travel works best when you’re running toward something, not trying to escape yourself. If this helps you think differently about long-term travel, slow travel, or finding your own travel style, subscribe for more, share this with a friend who’s dreaming about life on the road, and leave a quick review so more people can find the show. 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 . Available on Amazon at https://www.amazon.com/dp/B0H8TBR88L Available as a PDF along with other titles at https://jim-santos-books.square.site/ 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

  5. Jul 1

    Pack Lighter And Travel Easier With Simple Systems

    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 for every scenario, why complicated itineraries create clothing chaos, and how we now rely on lightweight luggage, simple layering, and quick-drying clothes to stay comfortable without hauling extra weight. We also get practical about laundry on the road, including why we travel with laundry sheets and how compression bags help us save space, stay organized, and avoid unpacking an entire suitcase for a short stay. Then we switch to travel apps and digital tools that actually earn their place on your phone. We explain why WhatsApp is essential for communicating with hosts and businesses abroad, how Google Maps or Apple Maps (and even Waze features) make navigation easier, and why Apple AirTags can help you track luggage and find your way back when you get turned around. We cover Google Translate for signs and appliance controls, cashless travel with Apple Wallet or Google Pay, and rideshare and transit apps like Bolt and BiTaksi that remove haggling and reduce the need for cash. Finally, we tie it together with the habits that prevent small mistakes from becoming big headaches: confirming details early, keeping confirmations accessible, handling time zone changes in your calendar, and building buffer time around check-in and travel days. If you want travel packing tips, the best travel apps, and a realistic approach to long-term travel planning, hit play, subscribe, 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 . Available on Amazon at https://www.amazon.com/dp/B0H8TBR88L Available as a PDF along with other titles at https://jim-santos-books.square.site/ 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

  6. Jun 24

    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. Available on Amazon at https://www.amazon.com/dp/B0H8TBR88L Available as a PDF along with other titles at https://jim-santos-books.square.site/ 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

  7. Jun 17

    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/ Available on Amazon at https://www.amazon.com/dp/B0H8TBR88L Available as a PDF along with other titles at https://jim-santos-books.square.site/ 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

  8. Jun 10

    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. Available on Amazon at https://www.amazon.com/dp/B0H8TBR88L Available as a PDF along with other titles at https://jim-santos-books.square.site/ 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

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5
out of 5
6 Ratings

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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