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
How Much Does Long-Term Travel Really Cost?
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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.
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"Wherever We May Roam: Finding Your Travel Style" - On Amazon
Why Money Stops Most Trips
JimMost people plan travel like a vacation, and that's the problem. Welcome to Wherever We May Roam, the new phase of Travel to 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. Hello, everybody, and once again, welcome to Wherever We May Roam, Travels with Jim and Rita. Now, today we're going to talk about a topic that's on everybody's mind nowadays, I would think, don't you, Rita? Well, absolutely. Yeah, if there's one thing that stops most people from traveling longer, it's this money. Especially now with the economy teetering and the price of gas, jet fuel, really everything just continuing to rise. Now we'll be looking at several topics, including how much does it cost, how do you figure a budget, how do you afford it, and what happens if things don't go as planned. Now here's the reality. Most people either overestimate what travel costs or underestimate how to manage it. And both of those can really keep you from ever getting started. One of the things you really have to understand is that when you say travel, there's not just one fixed cost to that. It depends on a lot of things like how you travel. Obviously, flights are going to be more expensive than uh most ground transportation. And in fact, we found that we can save a lot of money using ground transportation, right?
RitaRight.
JimWhere you go, of course, is going to affect that. There are some places, like uh we'll talk about some trips to Central America and Mexico, where the cost of living is very low. And then also there are trips to some places in Europe where the cost of living is a little bit higher. And of course, how long you stay can also affect things, but maybe not the way you're thinking. Because a two-week trip looks very different from a two-month trip. And then two months looks very different from full-time travel.
RitaIt does.
JimSo that's why trying to compare your travel budget to someone else's is usually not a great idea. Because everybody has different ideas of what they want to do when they travel, and they have different needs when they travel. So let's look at a simple way, first of all, to set your travel budget.
A Simple Budget You Can Use
JimYou want to total all the fixed expenses that you have per month. For most people, I think healthcare is probably one of the biggest ones, unless you're paying a mortgage or rent. The cost of maintaining your home while you're away, you're still going to have to be paying utilities, maybe at a reduced rate, but you have to account for that. It's much simpler if you're going full-time and don't have a home to maintain, but there can still be extra cost involved in that, like we uh paid a fair amount for storage.
RitaWe did.
JimNow once you've totaled your reliable monthly income, your net, not your gross. For us that was a pension and our Social Security checks. Now we have other sources of income, but they vary from month to month. So we didn't want to count them in our budget.
RitaAaron Powell And we did not want to touch our retirement nest egg.
JimYeah, but a big goal for us was not just not touch our nest aid, but we actually grew our nest aid while we were traveling. Hopefully, when you subtract the expenses from your income, you get a positive number. Now we'd like to use a figure of about 80% of that number as our monthly travel budget. Now, if your total is less than $1,000 a month, maybe you're not going to be to doing full-time roaming or anything like that, but you can set aside maybe a little bit each month and plan one or two extended vacations. Now, Ria, I think we found when you're doing just extended vacations or even some longer roams, what helps your budget a lot is you often are paying for some things like the airline and some of the accommodations. You're paying for those in advance.
RitaRight.
JimSo you can kind of spread the cost of the vacation over a bit of time.
RitaAaron Ross Powell Right. And and we also try to manage any of the airline costs with points.
JimRight. Now if if your total is somewhere between 1,000 and 2,000 a month.
RitaDepending on where you go.
JimYeah, depending on where you go, you can probably travel for two to three months at a time, uh maybe even twice a year. When you get up to 2,000 to 3,000, you're definitely in the part-time roaming ballpark. And more than $3,000, you may even consider full-time roaming, especially since losing the home base eliminates a lot of those monthly expenses. Trevor Burrus, Jr.
RitaRight. And then you could wrap up that home base, whatever money you would have left from selling your house into income as well.
JimRight. Now travel is a lot more affordable than you might think. And one of our biggest surprises was that longer travel can actually be more affordable on a per day basis. Because you're not rushing, you're not constantly moving, you're not paying peak rates for short-term prices. And another thing is we like to take advantage of the shoulder seasons.
RitaAaron Powell Yeah. Well and then your lodging bec is less expensive. Plus, if you can, if you can stay in a place for 30 days or 20 to 30 days, you get a discount. So that slow travel really stretches your money.
JimAaron Powell Also, another thing that helps is if you start living more like a local, because that's going to change your cost. Now you've heard us and you'll hear us again talking about the mercados. We love looking for the places where the locals are shopping, as that's always where you're going to find your best deals.
RitaAnd we have found in in like like Panama and San Miguel Allende DR. San Miguel.
JimSan Miguel de Allende.
RitaSan Miguel de Allende. You can't we we lived on $3,000 a month easily. Trevor Burrus, Yeah.
JimWhen we set our goal of uh full-time roaming, that was our planned budget was $3,000 a month. Now we knew some months it was going to be less than that, some months it was going to be more than that. But again, we had that 20% buffer built in, and then we had the uh variable income that we weren't relying on. Trevor Burrus, Jr.
RitaRight. And and there are other locations in Europe that you can do that as well. I feel like you could do that in Portugal if you're careful in where you get your lodging. And I think you could do that in southern Spain, not in big cities in Spain, but southern Spain, like Seville.
JimYeah, the Seville was pretty uh very reasonable. Pretty reasonable.
RitaYeah.
JimYeah, the two Euro beers and Right.
RitaBut then we jumped over to the British Isles and six dollar beers and seven dollar beers.
JimYeah.
RitaYeah. Yeah. So and then by the time we did our month in Ireland, we it was ten thousand dollars that month easily.
JimAaron Powell Yeah, we've had trips where we spent more than that $3,000, but it was because of the way that we are traveling. And that's what we mean by how much you spend is going to determine be determined in part by how you're traveling.
RitaTrevor Burrus, Jr. Because that was one of the only times that for a month we rented a car.
JimAaron Powell Yeah. The places that we've gone and stayed a fair amount of time, like Panama, Mexico, and even Seville, we ended up staying within that $3,000 a month budget.
RitaTrevor Burrus, Oh yeah, because we walked everywhere, or we used uh public transit.
JimRight.
RitaOccasionally an Uber.
JimAnd shopped locally.
RitaAnd shopped locally. Yes.
unknownYeah.
JimThat trip to Ireland uh kind of an aberration for us because rather than just having a city or two we wanted to see, we wanted to see the whole island.
RitaAaron Powell And we circled the entire island.
JimYeah. So we we circled the island.
Slow Travel And Lower Daily Costs
JimWe also stayed in a lot more places for shorter periods of time.
RitaRight.
JimIt wasn't a budget trip.
RitaNo. And and we and when you do that, when you're moving every four to five days, how many we counted that? Was it eight or nine different lodgings, some hotels, some Airbnb?
JimAt least I think it might have been a little more than that.
RitaYes. When you're doing that, you're paying a premium to do that because you're you're not accumulating any time there.
JimYeah, you're not getting that discount for a length of stay.
RitaAnd and where booking, we can get a 20 or 30 percent discount usually, and Airbnb, the longer you stay, you get a bigger discount. So you you decide on how you want to spend your money.
JimAaron Powell When you're thinking about any kind of extended travel, here's a few key things uh that are going to matter. Now, as Rita was just saying, accommodation is usually your biggest cost. So the longer you can stay in a place, the more of a discount you can get. That's really gonna affect the costs that you're having. Also, where those accommodations are. We mentioned last episode that you might find a very good rate on an Airbnb that's somewhere out in the countryside, but if you then have to spend a lot of money traveling around, it's not necessarily a bargain. So type of accommodation you're getting and how long you're staying is really gonna be uh important.
RitaAaron Powell And the use of ground transportation. I mean, Jim and I will use buses before a train or an airplane and lots of times get to our destination within the same amount of time or less.
JimAaron Powell Right, because of the time you have to spend getting to the airport and have to be there two or three hours early, uh wait for your bags and then travel from the airport to wherever you're going.
RitaSo airports are an hour's drive from the city that you're that you have your lodging.
JimSo right, and most ground transportation is in the city. Yes.
RitaAnd and we did use on our travels trains, buses, and and airplanes, but uh it seems in the last bit of our travel, other than in Ireland, we spent a lot of time on buses and it was very economical.
JimNow eating like a local, we mentioned also makes a huge difference in how much you spend, uh, as does your flexibility. Really helps you find better deals if you remember you're not buying a place, you're just staying there for a little while.
RitaRight. And as long as it's clean, has internet, it does not have to be the Taj Mahal, but it does have to be comfortable.
JimAaron Powell Right. And just as important, you
Lodging And Transportation Choices
Jimneed to always plan and expect the unexpected because things will definitely come up.
RitaOh, yes.
JimAnd the longer you're traveling, the more things are going to come up.
RitaRight.
JimAnd that's why we are really firm believers in travel insurance.
RitaAaron Ross Powell Oh, absolutely. I w I wouldn't travel at all without it.
unknownAaron Ross Powell Yeah.
JimNow I'm not talking about the kind that when you you book an airline, they'll ask you if you want to add a certain amount of money for trip insurance. Not talking about that. We're talking about travel insurance where you have coverage for the entire trip.
RitaAaron Powell Yes, for trip interruption or cancellation, like an Airbnb cancels you or a ferry cancels or the airline cancels. So you can get reimbursed for your loss.
JimTrevor Burrus, Right. For lost luggage, delays, if you your plane gets delayed an extra day and you have to stay in a hotel, you can get coverage for that. You even get medical coverage to cover any illnesses that happen while you're on the road, or if you have to cancel a trip because of an illness that happens while you're on the road. Even illnesses or deaths in the family. If you're traveling and find out that someone back home has some sort of major problem, you can file a claim for that and get some of the money back from your trip. Because you know, on a long trip like this, even if you're staying within, say, our $3,000 a month budget, if you're planning on traveling for three months, that's a fair amount of money you've got invested in that. And we found that uh we were paying around $1,000 a trip for trip insurance.
RitaRight.
JimRecently we started using Alliance, which uh let us uh sign up for one year of travel insurance. Trevor Burrus, Jr.
RitaIt was about fifteen hundred.
JimFor about yeah, twelve fifteen hundred, something like that.
RitaRight. For as many trips as you take that year. Yeah, as you take that year. Trevor Burrus, Jr.
JimBut the thing is with you know, so maybe we've paid uh three or four thousand dollars in travel insurance over the past few years. But we've got back in claims probably over fifteen thousand from that. So it's really uh an important thing to consider if you're traveling a lot because things really do happen.
RitaAaron Ross Powell They do. They do.
JimNow there's uh also a few simple strategies you can use to try to save some money. Uh first of all, build a buffer into your budget and track the spending early in your trip because you'd be surprised how quickly little things add up.
RitaYeah, it can sneak up on you.
JimYeah. Just, you know, a snack here or there, taxi, uh museum fees, anything like that. You'd be surprised how quickly that adds up. Really uh take a good look at the big cost that you're spending here too. And if you're tracking like that, then you kind of adjust as you go. And you get a better idea for what's going to be within your budget and what's going to be a splurge. And there's nothing wrong with splurging
Travel Insurance And The Unexpected
Jimas long as you realize it.
RitaAaron Powell No, we do. And we do splurge. I I can't say that we've said, oh no, we can't afford to do that. If it's something that's important to one or both of us, we do that.
JimRight. But one of the uh cleverest things that uh Disney ever did was to give you a card that you could use if you're staying in the Disney resort. Yeah. Oh, just use this card wherever you go. You know, you don't have to take out money, just use this card.
RitaYeah.
JimAnd you end up just using it and using it and using it, and then you go to checkout and you've got a five-figure bill.
RitaYeah.
JimSo keeping track of things is really going to help you a lot. Now the travel budgeting isn't about perfection. You don't necessarily have to watch every single penny, but it's about awareness. It's about being aware of what you're spending.
RitaAbsolutely.
JimNow another thing that we've found is we very heavily use credit cards. Uh we pay for virtually everything on credit cards and then pay off that bill at the end of the month so we're not charged interest charges on it.
RitaTrevor Burrus, Jr. But we're building points.
JimTrevor Burrus, Jr.: Yes, we're building points. So we found the two that work best for us are Chase Sapphire Preferred and the American Express credit card. They both seem to be more generous with the points, and you get more benefits from that. Trevor Burrus, Jr.
RitaThey have n nice lounges as well.
JimOh, yeah. Getting into the lounges is a great thing. And talk about saving money.
RitaRight.
JimWhen you can get a free meal at an airport, that's going to save you $50, $60 for you know a rubber chicken sandwich.
unknownRight. Right.
RitaOh, yeah.
JimSo we thought that would really help a lot. Yeah, I didn't want to give the name.
unknownOops.
JimAnd we accumulated a lot of points, but then when we would go to use it, it was almost worthless. Right. You needed such a huge amount of points to get anything. But we found that that Chase and American Express cards really do seem to be worth it. For example, we once flew from Mexico to Knoxville for just $12 for the two of us. And actually that included some first-class seating that we didn't get to use because our plane was delayed.
RitaAnd we s and we did standby and and we were in coach on the standby, which was fine. Trevor Burrus, Jr.
JimYeah, rather than staying until midnight, we got on a standby list. And since we are using first class tickets, they were more than happy to bump us up to first.
RitaYeah, and and bump.
JimAnd let somebody else pay for the pay for the first class. We also flew from Knoxville to Lisbon absolutely free using points. And when we came back from that trip, we flew from Dublin to Knoxville for a total of $300.
RitaRight.
JimSo that alone, using being able to use those points, saved us several thousand dollars in airfare.
RitaWe really don't think about our flights as an expense for a trip because we're really going to get it very inexpensively. Trevor Burrus, Jr.
JimYeah, we don't look at these uh big trips, the big uh the big transportation costs as part of that 80 percent of our budget. Partly because we generally are getting them, you know, well in advance.
RitaYep.
JimAnd also because that's kind of what that 20 percent and our other income is is for, trying to keep that off the uh the day-to-day life. Now when you're picking accommodations,
Tracking Spending And Using Points
Jimthere are a lot of services out there like Expedia, uh Booking, Trulago. They're all pretty much the same. I think some of them are actually owned by the same companies. But if you pick one that you like and continue to use it, you're going to eventually build up points with them, which are good for discounts and special rates. Now we've been using Booking.com uh for decades now.
RitaRight.
JimAnd we pretty routinely get anywhere from 30 to 40 percent off the cost of the hotel room. Uh we'll get perks like free ride to or from the airport uh to the hotel, and that's gonna save you some big money right there.
RitaAaron Powell And you know, there's a lot of positive and negative things flying around about Airbnb, but we have used them so much that if we do have an issue, they address it.
JimYes.
RitaThey address it right away. We document the issue and we're always satisfied at the end.
JimAaron Ross Powell Right. In fact, on a recent trip to Glasgow to Glasgow, the first accommodation we went to really was not livable.
RitaNo, it was awful.
JimIt wasn't in a great part of the city and it was very dirty. There were dead bugs on the floor.
RitaYeah, we said we're not doing this.
JimIt technically had a washing machine, but to use it you had to unplug the refrigerator and move it out of the way to plug in the washing machine.
RitaRight. We have never had I mean, on it when you looked at the site, it looked like a beautiful little bit.
JimIt looked decent, yeah. But the pictures don't always match.
RitaNo, they don't reality. No.
JimAnd we documented everything, we took lots of pictures, we told the host right away it wasn't livable, and we contacted Airbnb. After they analyzed everything and got back to us, they told us there wasn't enough evidence to say that it wasn't usable. But they still refunded us the money.
RitaRight.
JimAnd they said they did that because we had been using them for a while and had good reviews. So, you know, again, whichever one you're using, stick with it.
RitaStick with it. Yeah. Because that we've actually only, in all the years of travel, only had two condos that we ever had to complain about with Airbnb. And and one time we had asked the the landlord for a small discount because we had spent so many days in the condo waiting on repair people to fix the air conditioning. So we had asked for a small amount and w and they wouldn't give it to us.
JimShe offered to let us stay longer.
RitaYeah. Longer and hot in the heat. We said no. But but when Jim mentioned it to Airbnb, they they gave us twice what we were asking for.
JimThey gave us almost twelve hundred dollars. In a refund.
RitaYes.
JimAnd it wasn't just asking them. Again, it's important if you run into problems like this. You have to document we had pictures of the water spewing from the air conditioning units, pictures of the water dripping down the wall, and pictures of the water stains on the bed and on the uh on the couch.
RitaYeah.
JimAnd I had screenshots of all the communications with the owner about the repairs. So we had a lot of documentation to back up what we were saying. Trevor Burrus, Jr.
RitaAnd the number of days that we had to stay in the condo to let people in to make repairs. Aaron Ross Powell Right.
JimSo they ended up uh discounting each one of those days.
RitaRight.
JimWhich was a a great deal for us.
RitaTrevor Burrus It was.
JimAnother thing that that we do and that we think really helps cut down costs is we really try not to backtrack.
RitaAaron Ross Powell Yes. We don't do round-trip tickets. Trevor Burrus Yeah.
JimI mean if you're you know if you're going to just Mexico and staying in a couple places, maybe it does make sense to get a round-trip ticket there. Sometimes we'll get nested round trip tickets. We just really hate to backtrack. You know, if we've already seen an area, we don't really want to go back to it. And we found that really when we're booking one-way travel,
Booking Loyalty And Airbnb Proof
Jimit's really not more expensive than if we were booking round-trip tickets, especially because you don't have to return to that airport. You don't have that extra expense of getting back there.
RitaRight.
JimAnd there's really no sense in airline cost at all. You know, we've found uh once coming back from Dublin to Knoxville, if we booked a straight trip through, it was about fourteen hundred dollars for the two of us. If we booked a trip from Dublin to Dulles Airport and then from Dulles Airport to Knoxville using exactly the same flights, the same airplanes, it was seven hundred dollars.
RitaSo what do you think we did?
JimSo yeah. And something else I I did want to mention about one-way tickets. We've heard a lot of people tell us you have to have a round trip ticket if you're gonna fly into this country because they won't let you through passport control if you don't. And we have never found that to be true. We use one-way tickets all the time.
RitaYeah.
JimRemember once in Berlin, the guy asked us when we were returning, do we have a round-trip ticket to return? And we said no, we're taking a train from here to Prague. And he just shrugged and stamped our passport.
RitaYeah.
JimYeah, it wasn't a big deal at all.
RitaAs long as you're not gonna overstay your visa or the amount of time that you're allotted to stay on your passport, they don't really care. Aaron Powell Right.
JimAs a matter of fact, that's our next episode we'll be talking about visas and the Shenzhen zone. But for now, I want you to remember that the goal here is to save money, definitely, but the it's not to travel as cheaply as possible. It's to travel in a way that's sustainable for you and that works for you. And that's what will allow you to keep going when you're taking extended trips.
RitaYeah, I I agree. And with what Jim said about you don't want to feel like you're missing out. If you have spent a lot of time and effort to get to a certain location, see that location. It doesn't mean that you have to do every tourist trap or whatever there that there is there, but you pick out what's important to you and see it. Because you're not going back there, probably. It's just not going to happen. Although we have gone back to some locations. But we have.
JimBut we found though also that photographs are more or less free.
RitaExactly.
JimSo those days of having to buy film and pay for processing and developing. We would be broke if we had to do that.
RitaOh yeah.
JimYeah. So yeah, you'll find uh more travel tips and hints, more information on budgeting and that in the book, uh, wherever we may roam, finding your travel style. And next time we're going to be taking a look at something that is very confusing sometimes for people, and that's visas, extended
One-Way Tickets And Sustainable Travel
Jimvisas, the ETIAS system that's rumored to be starting anytime now, and of course the Shen Jin rules for visiting Europe. So we'll talk about how to travel safely and how to stay longer legally. So that's it for this episode. As always, 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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