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.
Wherever We May Roam - Travels With Jim and Rita
Travel Smarter In An Uncertain World
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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
"Wherever We May Roam: Finding Your Travel Style" is available on audiobook on Amazon, Audible, and other audiobook outlets!
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"Wherever We May Roam: Finding Your Travel Style" - On Amazon
Welcome And The Travel Mindset
JimHave you ever spent weeks planning what felt like the perfect trip, only to watch the news and wonder if you should even bother? Welcome to Wherever We May Roam, the new phase of Travels with Jim and Rita. This podcast is about discovering your own travel style to explore the world. I'm Jim Santos, and along with my wife Rita, we've spent more than 16 years traveling. Sometimes for a few weeks, sometimes for a few months, and sometimes a whole lot longer. And what we've learned is this there's no right or wrong way to travel. Some people take extended getaways, some roam part-time, some work from the road, and some make travel a full-time lifestyle. This podcast is about helping you figure out what works for you and how to make it happen in the real world. So whether you're planning your next trip or thinking about something bigger, we're glad you're here. Let's get started.
Planning When The World Shifts
JimHow do you plan a long-term international trip where the world keeps shifting underneath you? And we know that visa rules can change without notice, flight schedules get revised, political situations that seem stable suddenly aren't, and the cost of everything, of course, keeps climbing. But here's what we want to establish right from the start. Today is not about fear. We're not going to spend the next half an hour making you feel like the world is too dangerous to explore. We're going to give you practical tools to plan smarter, to protect yourself, to protect your investment, and still get out there and experience this extraordinary world. Because the world is still out there and it's waiting for you.
RitaI am. But we we've normally just gone anyway after we've weighed the pros and cons. I mean, we spent 2024 going through Eastern Northern Europe and during the well, and it's still gone on, the Russian Ukraine conflict. We really did want to go through Belarus and go see St. Petersburg. But of course we didn't or wouldn't because it seemed like pushing our luck a little bit. Yeah, it seemed like that that's extremely crazy. And those are the pros and cons you go through. Trevor Burrus, Jr.
JimYou know, something we heard all the time as expats also was is it safe? Right.
Safety Fears And The News Gap
JimEveryone's just preoccupied with safety in other countries. And I think really part of that, I always go back and blame the 24-hour news cycle. Trevor Burrus, Jr.
RitaRight.
JimI've read uh books by historians who said that actually right now in history of the world, history of civilization, we have fewer people at war, smaller percentage of people at war, much fewer people in poverty levels, life expectancy is you know at highs right now. But you're constantly bombarded by this news coverage that shows you all the bad things that are going on. So there there's really a perception gap between the news coverage and what's actually happening on the ground.
RitaYeah, and I've always said nothing good happens after midnight. So if you're home if you're at your hotel or whatever lodging you have tucked in your bed, you know, the world goes on outside around you, but you're not involved.
JimAnd it is true that at one point having an American passport, that was like the gold card. You know, you you it was looked at with respect and you automatically had goodwill. And frankly, that's not really the case right now.
RitaNo, it isn't.
JimAlthough I have to say that in dealing with people in other countries, I've never really felt like they were anti-us.
RitaNo. No, because they're just normal people like us. They're not involved in the political regimes that are going on.
Advisories And Regional Risk Reality
JimYeah, and if you look at the State Department website, they're their advisory levels are pretty simple and they're not really that comprehensive. The difference between a country-level risk and a regional area risk is not always really well defined. A good example of that is Mexico. Yeah, right now the northern borders of Mexico is definitely some dangerous areas. There's definitely some stuff going on there.
RitaRight.
JimBut you know, we've been to the uh the Cosamel area, Cancun, and the little mountain village of San Miguel de Aliente, and those are pretty peaceful places.
RitaRight. Oh yeah, I would go again. Yeah.
JimYeah, that doesn't mean you shouldn't check out travel.state.gov. You should bookmark that and look just to make sure, you know, what might be happening as you're planning your trip and and before you go on the trip. But keep in mind that I mean, I I've looked at this website before. They advised about the dangers of traveling to Canada.
unknownRight.
RitaYeah.
JimYou know, anywhere you go, there's going to be some pockets that you should stay out of. But it it it helps to at least have that information.
RitaAaron Powell Yeah, I mean the U.S. is the most gun-toting country in the world. I mean, come on. Probably we're safer outside.
JimAnd keep in mind there's there's almost always some place where it's pretty safe that you can go.
Safer Destinations And Places To Skip
JimRight now, for instance, uh my son's been to Japan a couple of times. And he'll tell you that the people there are just so polite, uh, the crime uh level is is really low, and they have a culture of providing comfort to visitors and travelers.
RitaAaron Powell I mean it's such a clean country. Trevor Burrus, Jr.
JimYeah. Yeah, very clean country. Places like Portugal, I think it's been over 150 or 200 years since Portugal was involved in any war. New Zealand, of course, the Nordic countries are frequently listed as some of the safest places on earth. Uh Costa Rica in Central America has a very good reputation. And then, of course, Vietnam. Surprisingly enough, we know a couple of people who have been to Vietnam and said that they really loved it there.
RitaYeah. It's so beautiful, too, and uh inexpensive.
JimYeah. And of course, there are the places that you probably really do not want to go. Uh Haiti, for instance. They've had a reputation for violence as long as I can remember.
RitaRussia, Belarus.
JimYeah, isn't that a great time to be checking out a condo in Belarus or anytime there's a conflict zone, I'd rather be out of it.
RitaTrevor Burrus, Jr.
JimRight. It's not a don't want to look for seaside property on the Strait of Hormouths right now.
RitaNo.
JimBut all of this changes. I mean, places that were thought to be too violent just a few years ago are now very peaceful, and and it's gonna vice versa, it's gonna happen again.
RitaAaron Ross Powell
Visas And New EU Entry Systems
RitaRight. And these types of trips, you are gonna plan six to nine months out to get the best deals. And it takes a long time to plan these types of trips out if you're going out for three or four months. Aaron Powell Right.
JimWe're already training planning an 84-day trip that won't start until late March of this year. And a lot can change over that time. Trevor Burrus, Jr.
RitaRight. So it's always you always need to be flexible. You can always, you know, take a block of your trip out, rearrange it into another country or whatever.
JimThis kind of long-range planning, of course, does have some problems with it. For instance, visa rules can do change with very little notice. And you can't always count on blog sites or even podcasts for that matter, for the most up-to-date information. That's right. Frequently you have to go right to the source. And I really recommend that you look at the embassy site for the countries involved.
RitaRight.
JimYeah, that's going to have the most up-to-date information. There's also the IATA Travel Center, which is a third kind of blog, but you know, I'd I'd really check right with the embassies directly. Then there's also some new programs. In theory, you have to register on this ETIS site and they check you for priors and make sure that you're not on the travel list or anything. You pay like a 20-pound fee and you're good for the next uh five years.
RitaAaron Ross Powell And that's a the Europe site.
JimTrevor Burrus And the problem is that's been any time now for the bet about three years. Trevor Burrus Right.
RitaWe have to look every time we book something.
JimYeah, and they're currently saying the fourth quarter of this year, but you never know. What we've done is gone to that etias.org site, and there's a place there where you can put in your email address and ask them to notify you when the system's up and running.
RitaTrevor Burrus You you really should try to do that before, but Jim and I have been caught in a situation like onto Turkey that we became aware that you had to have it, and we got on our phones in Greece and applied for the $50 visa online, and it was granted. Trevor Burrus, Jr.
JimYeah, we were unaware of it until we were actually at Thessaloniki at the counter.
RitaYeah.
JimAnd uh the woman told us, you know, you have to have this electronic authorization, don't you? Trevor Burrus, Jr.
RitaNo, but we will get that.
JimThe other system that has has recently just come online is the EES in Europe. This is something that the EES is a system that will use biometric data rather than your passport when you're entering uh the EU and Shenzhen zone areas. The first time you encountered this system, you may need to scan your passport, but then it will also take a scan of your face and maybe fingerprints. After that, whenever you cross a border, you just go up to the kiosk, it scans your face or fingerprint, and that's it. You don't have to take your passport out, it doesn't get stamped.
unknownTrevor Burrus, Jr.
RitaIt's not up and running, though, is it?
JimIt's just started in April.
RitaOh, it is.
JimAnd some of the bigger choke points like uh uh coming out of the tunnel, the airport in things Amsterdam, which has a lot of international traffic.
RitaRight.
JimAnd I know when we were last in Portugal, we saw just dozens of the kiosks that were still wrapped, and they were getting ready to put those out.
RitaYeah, that was last spring. Yeah.
JimSo all of these things you do need to make sure that you're keeping an eye on. They have nothing to do really with the safety of travel. It's just some of the logistics and some of the little minutia that can be a little overwhelming sometimes.
Inflation Airfare And Currency Swings
RitaI think the biggest thing going on now for planning these trips so far out is the economy.
JimYeah, especially the airline prices. Right. Right now, fuel costs and route consolidation has driven up prices for some airlines. Spirit Airlines, for instance, just recently folded completely. Trevor Burrus, Jr.
RitaAnd the price of the dollar. I mean, they yeah, the value, I should say, of the dollar. Trevor Burrus, Jr.
JimYou know, you you want to make your reservation early enough so that you can sometimes get a discount and you also don't want all the cheap fares to be gone. But on the other hand, as fuel prices go up and they decide to consolidate routes, what what is the direct flight might suddenly become a flight that has two or even three stopovers someplace?
RitaAaron Powell Not a fan.
JimYeah. Like the direct flights. Unless we have a lounge.
RitaYeah.
JimYou mentioned uh currency swings. You buy a trip based on one exchange rate, by the time you're ready for departure, it may have changed 15-20 percent in either direction.
RitaRight.
JimSo you need to build in a cushion whenever you're planning your budget for trips. And of course, the big thing, this is Rita's particular bugaboo, is the uh geopolitical wild card.
RitaYeah.
JimMy stance is you can't predict it, you can't do a thing about it.
RitaCan't do a thing.
JimWill something happen? We really don't know. Am I protected as if it does, is something that you can do something about through things like uh uh trip and interruption and cancellation insurance.
RitaRight. I don't know if I'd come back or would I run in the opposite direction. That's the problem.
JimI think our most recent trip when we went to Portugal, Spain, UK, and Ireland, we probably started planning that about eight or nine months ahead of time.
RitaRight.
JimAnd it did change as it got closer because you know we had things come up that we hadn't accounted for. We had made some changes in how we were going to get from place to place.
RitaThen we added another country, you went to Spain. Trevor Burrus, Jr.
JimYeah, we went to Spain because uh turned out I had to go to an international living conference and we found a flex bus rate, I think it was $12 each to get us to Spain.
RitaSo that's all it takes to get us going to someplace else. That sounds exciting.
JimAaron Powell So no matter how early you start, it's going to change before you get there. Not necessarily in a bad way, but you you need to have enough flexibility in your travel plan so that you can deal with that. Trevor Burrus, Jr.
RitaLearn how to pivot.
JimNow, do have to talk about travel insurance. Really cannot say enough about the importance of having travel insurance. It it's not an option. It should be part of your infrastructure, it's part of what you always do when you're planning a trip, especially to Europe. You know, we have I think we've mentioned before in this show that we've spent maybe three to four thousand dollars on travel insurance on various trips, but we've been reimbursed for well over fifteen thousand dollars.
RitaYes.
JimSo it's really been a lifesaver. There are some things that you can look for. Uh the gold standard is kind of something that's called CFAR, cancel for any reason. Although if you want to buy that
Travel Insurance That Actually Protects You
Jiminsurance, it is going to cost more than your basic travel insurance. And you have to buy it at least within 14 to 21 days of the first deposit you make for the trip. So we're already past that on the trip or planning.
RitaRight.
JimYeah, we put a deposit down on something uh back in April. Trevor Burrus, Jr.
RitaAnd honestly, if there was something politically happening in some country, some kind of horrific thing going on, we would probably just move to another country. We would not come back.
JimAaron Powell Yeah, we would do the safest thing that we can do at the time. And we've traveled enough so that we'd be comfortable with going to a different country. Trevor Burrus, Jr.
RitaYeah.
JimNow the other thing you should know about the CFAR is that it generally will reimburse only 50 to 75 percent of the non-refundable cost. Where it comes in handy, though, is most insurance has strict rules for what they consider an interruption or what they consider a cancellation. You know, if you have death or serious illness or something like that, then sure, they'll cancel it. They'll even do it for death or serious illness in the family. But with the CFAR insurance, you can just say, I just had a bad feeling about it. You know, I just don't want to go right now and still get that 50 to 75 percent reimbursement. The other thing to make sure that your trip insurance and cancellation has is some kind of medical evacuation. And usually I would recommend at least $500,000 minimum for that. And I know that sounds like a lot, but expenses can really pile up. And there can be other circumstances. Like when we were leaving Latvia and I had been in the hospital for nine days, really could not have taken getting on two or three different airplanes and sitting in coach.
RitaNo.
JimEspecially the one overnight.
RitaNo.
JimSo we went ahead and booked last-minute first class tickets.
RitaRight.
JimWhich were fairly expensive.
RitaThey were.
JimBut we got reimbursed all of it for that. So it was definitely worth having that. And if you're in a situation where you're someplace where you have to be airlifted out and move to somewhere up, th those costs can really pile up quickly.
unknownTrevor Burrus, Jr.
RitaYeah, we've absolutely used that insurance well actually three times majorly.
JimYeah. Yeah, we've used insurance purchased for a single trip through the American Express website. It's not their insurance. You don't have to have a card to get it, but you can get to it through their website. Trevor Burrus, Jr. And it is excellent. It is excellent. And we've had no problem getting returns from them when we filed. We used Alliance once. We took a one-year policy. And actually the only time we tried to file a claim, they denied it. So I don't know if that's standard. Oh, wait a minute.
RitaWas that the medical coverage? Because we ended up getting medically the medical coverage paid through our insurance is back home. Trevor Burrus, Jr.
JimNo, this was on the trip in England and Ireland. And we didn't have to pay anything for your medical expenses.
RitaOh, that's true. Trevor Burrus, Jr.
JimBecause the country provided it for free. The only thing that we tried to file a claim for was when we were told we couldn't use our Airbnb in Dublin. Because it was a violation of the renter's lease.
RitaAaron Powell Yeah. And their subletting was not allowed. Aaron Ross Powell Yeah.
JimAnd the insurance company said that that was not an accepted excuse.
unknownRight.
JimSo they wouldn't pay the difference between that and our hotel stay.
RitaTrevor Burrus But didn't Airbnb eventually gave us some money. But the hotel was so much more expensive than the Airbnb, we just had to eat that cost. Trevor Burrus, Jr.
JimYeah, it was twice as much as the Airbnb. Trevor Burrus But so having insurance has really come through for us every other time that we've ever had to file a claim.
RitaTrevor Burrus, Jr. Right.
JimSo I guess the bottom line there is when you get your insurance policy, whatever it is, make sure that you review it, make sure you read the exclusions so that you know of what you have and when you can use that. Now there are some sites like insure my trip.com and square mouth.com where you can compare different type of coverage from a wide range of places. So those are all very much worth checking out.
RitaAnd sometimes when you like with Airbnb, if you cancel within a certain length of time before your booked stay, they do return your deposit that you have. Trevor Burrus, Jr.
JimYeah, every uh person who puts their home on Airbnb kind of has a different policy. So it's important to read that carefully. And w we always take pictures of everything when we first arrive at an Airbnb if something looks like it wasn't as advertised or was dirtier than we expected or was broken. We always take pictures of it and document it right away. Aaron Ross Powell Getting back to airfare, the problem with trying to book an airline when you're really not sure of what the world situation is, is it better to be early bird or go last minute? Well peak season routes to popular destinations always fill up fast. So those who generally always have to go, I'd say a good three months ahead of time, three to three or four months ahead of time. If it's less traveled and there's a lot of different airline options, then maybe you've got some flexibility and you can wait and watch for a sale. It has a lot to do with the time of year that you're traveling as well. But if you're using Google Flights, when
Claims Lessons And Policy Exclusions
Jimyou've picked your uh your flight that you like, you don't have to purchase it right away. You can ask it to set an alert for you. So it'll let you know if the price comes up or down. That can help you to plan when you need to move on it. It's also a good idea to go directly to the airline's website when you do find a flight that you like and check out their change and cancellation policies. In some cases, it might be worth slightly extra fare if you can make your change or cancellation without a fee. Now there are, of course, we mentioned Spirit Airline. Any of the budget lines, Ryanair, JetBlue, JetBlue, yep, they're going to be cheaper. They start off cheaper.
RitaRight.
JimBut if you're paying for your seats and you're paying for your checked bags, and you're paying for your carry-on, they may not end up being cheaper. And also it's the budget airlines that tend to have the sudden changes and the misconnections and that kind of thing. Trevor Burrus, Jr.
RitaAnd no reimbursement for cancellation and all kinds of crazy things. Trevor Burrus, Jr.
JimYeah. Some of the airlines that are worth mentioning are like Singapore Airlines, uh, Emirates Air, we've been very happy with. Right. Uh Lusansa. I understand Qatar is very good too. We haven't used them ourselves yet. And uh one personal favorite for ours in uh Central and South America is COPA Airlines.
RitaAaron Powell Oh, they were they were the bombs.
JimYeah, I don't think we ever had a delay of more than two or three minutes. No. They usually took off a little bit early.
RitaAnd they would give you the option of upgrading.
JimYeah, you could do upgrades on that. They also would occasionally have uh a situation where if there were extra first-class seeds, you could bid on it.
unknownTrevor Burrus, Jr.
RitaThat's right.
JimNow there are 10 things that you can do to try to help out with your planning in the state of the world right now. Number one is it doesn't hurt to register with STEP. That's stip.state.gov. It's free, it only takes about five minutes. Basically, you're just putting in information about yourself and your passport and where you plan on traveling and what dates that you're planning. You can get updates on any geopolitical changes in that situation. And in the event there is a problem, the State Department already has all of your information on hand. You can also get travel-friendly credit cards or American Express cards, in fact, have uh built-in insurance coverage for car rentals. We had a claim once on a car rental in Ecuador. The the company was trying to charge us for repair of the engine.
unknownTrevor Burrus, Jr.
RitaRight. $3,000. $3,000.
JimYeah, they were charging it for us. And I mentioned it to American Express at one point, and they said, oh, why don't you just submit it for a claim with us?
RitaRight.
JimAnd we did, and like four days later, they had paid off the bill. We mentioned the CFAR insurance, but remember you have to do it within 21 days of your first deposit. It's a good idea to use your calendar on your phone or or iPhone to remind you to check advisories every three weeks or so until departure. It's also a good idea to check with the airlines. Remember, we had a flight once a cheap flight from Dubrovnik in Croatia to Barcelona. And when I went to check
Booking Flights And Avoiding Budget Traps
Jimto get the flight times, it had been canceled. Right. And no one had told us anything about it.
RitaRight.
JimSo again, it's the Cheapo Airlines. We also think it's a good idea to photograph and do cloud backup of all of your important documents. That includes all of your flight information as well. Make sure that it's cloud stored also so in case you do lose your phone, you still have a way of accessing it.
RitaRight.
JimIf it's a real danger area or questionable area you're going to, it doesn't hurt to know where your nearest embassy is before you enter the country. And I always like to learn at least 10 words in the local language. You know, the kindergarten words. Yes, no, thank you, please. You're welcome, bathroom, you know. Usually sitting on the bus, I'm going through Google Translate trying to learn these words on the way to a new country. It really helps. It really helps lower the temperature of everything when you're talking with people. And no matter how badly you mangle the language, they always appreciate the effort. Trevor Burrus, Jr.
RitaOr at least smile.
JimRight. At least smile. I mentioned when you're budgeting for the a trip, any trip early, we try to build in a fifteen to twenty percent cushion to accommodate for things like currency changes and cost fluctuations. Even just, you know, with the price of the euro, with the euro going up and down, mostly up right now.
RitaRight.
JimThat can really make a big difference in your budget. Again, that sweet spot for booking is usually within a four to six month window for most long-haul trips. Longer than that if it's a very popular destination or a very popular time of the year. And number 10, I think Rita is the most important thing. Go anyway.
RitaYes, go anywhere.
JimI mean, it's natural to be concerned right now. It's natural to have second, third, or even fourth thoughts. But really, the world is such a big place and such an interesting place.
RitaRight.
JimAnd out of this whole wide world, there's such a small part of it where there's really an actual physical danger. So you really need to get out there and see the world while you can. So that's it for the show. I hope that we've at least eased your mind a little bit about traveling in an uncertain world. Remember that we still think the travel is worth it. We don't mean to scare anybody. We just want to equip you with the tools that you need to stay as safe as you possibly can. And there'll be links in the show notes for the uh travel departments and the insurance departments that we mentioned during this program. Next up, for next episode, we're going to take a look at a place
Ten Practical Steps Then Go Anyway
Jimthat we visited quite frequently. We were really surprised by how quiet and empty this location was, especially during Memorial Day week. So until next week, remember we travel not to escape life, but so that life does not escape us. If you've been thinking about traveling longer or just traveling better, we hope this episode gave you a few more ideas. Remember, there's no right or wrong way to explore the world. Only the way that works for you. 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 at jimsantosbooks.com. Thanks for listening, and as always, safe travels wherever you may roam.
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