Wherever We May Roam: A Practical Guide To Longer Travel

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.

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Transcript

Travel Is About How You Do It

Jim 0:00

Most people think travel is about where you go, but after years of doing this, I can tell you it's really about how you do it. 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 and welcome everybody, Phone the Neighbors, Wake the Kids, and welcome back after a long hiatus to the third season of Travels with Gym and Rita, now rebranded as Wherever We May Roam. Why the change? Well, fans of the podcast will recall that we started Travels with Gym and Rita back in January of 2024, when we first started the process of selling our home and setting out on the road full time. Things didn't quite work out the way we planned, did it, Rita?

Rita 1:28

Nope, not quite.

Jim 1:29

Now we've gone back to part-time roaming, and in fact we completed a successful spring trip in 2025 that included Portugal, Spain, the UK, and a month in Ireland. After that we decided to take a break from the podcast and travel so I could write another book. And as usually happens, I grossly underestimated the amount of time and work involved. You know, you've had one child when you decide to have another and you're all excited, but you forget how much pain and how much time it took.

Rita 1:56

And all the hard work.

Jim 1:57

Yeah, well, that happened to me. I had planned a Christmas launch, and that slipped to Valentine's Day and then to Easter. But at last I finally managed to get everything wrapped up and hopefully everything will be out by Mother's Day. So we're back to planning our next trip, back with the podcast, and happy to announce that the new book, Wherever We May Roam, Finding Your Travel Style, is now available on Amazon in Kindle, Paperback, and Audiobook. Hence the rebranding of our podcast and a new season. So what's it all about? Well, if you've ever thought about traveling longer than a typical vacation, maybe a few weeks, a few months, or even full time, you've probably realized something. There's no right way to do it. And that's exactly why I wrote this book. Because most people don't fail at long-term travel. They just don't know what kind of traveler they are. Planning for more than three weeks of travel is not like your prototypical vacation. Each style requires a different level of planning and commitment. And Rita, we've tried them all, haven't we?

Rita 2:56

Absolutely. We've been together for 16 years, we've done vacations, we've lived at X full-time expats in South America. We did short trips, long trips, and been digital nomads.

Four Long-Term Travel Styles

Jim 3:11

Yep, and after years of that traveling, we started to see a pattern. Now we're not talking about the casual tourist, and you know, there's nothing wrong with that. Any kind of travel is a good idea. But people interested in longer experiences abroad seem to fall into four main types. The extended getaway traveler, the part-time roamer, the digital nomad, and the full-time roamer. Now there can be some crossover between these, and we've certainly been into at least two or three different categories at the same time, right?

Rita 3:39

Yeah, that's true. While living in South America, we spent months traveling there as well.

Jim 3:46

The biggest mistake people make is trying to plan one type of travel using the rules of another. Now we'll get into each of these styles in future episodes, and you'll see that each one has its own peculiar pluses and minuses, and each requires different approaches. Now, what will work best for you depends on a lot of factors. Right, and I think our goal is to let you know what the challenges are and the rewards of each, and then it's really up to you to develop your own style within that form. Now, some of the things that you need to consider is, well, first of all, how much time can you spend on the road? And how many times a year can you do that? Reader, probably for most people, that's one of the biggest challenges.

Rita 4:29

Right, and we're retired, so we are super flexible.

Jim 4:33

And kind of following hand in hand with that is what kind of travel budget do you have?

Rita 4:37

Right.

Jim 4:37

And again, that's probably going to be wildly different for single people if you're married or if you have children, or if you're retired like us and have a little more time on your hands. Now we don't have a mortgage, don't have car payments, so that kind of frees up a a lot of uh time and money for us for travel.

Rita 4:52

That's correct. That's correct.

Jim 4:54

Also, are you still employed? And if so, is your job portable? Now we've had some experience with that as well.

Rita 5:00

Right. When we were s both still working, we wanna went on an extended trip to Italy for the for three weeks and uh did some of the crazy things like going into internet cafes and getting getting a drink so that you could have free internet. So yeah, we've we've made it work for us no matter what we were doing.

Jim 5:22

Right while we were both working, we also spent an entire week in New Orleans.

Rita 5:26

Right.

Jim 5:27

Both trying to work during the day and having vodka and donuts for breakfast.

Rita 5:30

Right. That that might have been a plus or a minus, I'm not sure.

Jim 5:35

And then there's also the question, is your job seasonal? And people people in the education system come to mind. Maybe you have a few weeks or a few months each year when you're available to travel. Now the downside of that, of course, is that that's when everybody is traveling.

Rita 5:49

Right. And especially if you're not fond of really hot weather, shoulder season seems to work the best for us.

Jim 5:56

Yeah, it's uh the hot weather and the big crowds are really something we like to avoid.

Rita 6:00

Oh yeah, I hate that.

Jim 6:02

And of course, it's also important are you a solo traveler? Are you traveling as a couple? Do you have kids? And are you traveling with pets? But we've interviewed people who are in all of those categories.

Rita 6:13

Yeah, we have, and it's been so interesting. I mean, we ourselves took pets for our our life when we lived in Ecuador. And it all works out. It just depends on planning for it.

Jim 6:25

Right, and our friend uh Claire East, who introduced us to Flixbus, she's traveling solo.

Rita 6:30

Right.

Jim 6:31

And we've interviewed a woman, I think in our second season, who was traveling with children, and we also talked to a woman who was traveling with children who were autistic.

Rita 6:39

Yeah, we did, and and they really enjoyed their travels.

Jim 6:43

Yeah, so I guess the point of these things is that none of this is something that can keep you from traveling. They're just things you have to incorporate into your traveling style.

Rita 6:52

Right, and plan for it. When you really have to be flexible, I mean you just can't uh let anything derail you. You just you just have to realize you're there to enjoy it, and no matter what happens, you'll you'll make it work out.

Jim 7:05

Right, and that's one of our points. Do you fluster easily or need to have things rigidly planned in order to feel comfortable? So we have found that often plans just do not work out.

Rita 7:15

Yeah, you might plan on a long stay in a location that after you get there, you realize, hey, I've been here five days and that is enough. We need to move along.

Jim 7:27

Or the opposite. Uh we only planned uh a couple of days in Vilnius.

Rita 7:32

Right.

Jim 7:32

And uh it was a beautiful place. Would have loved to spend more time there.

Rita 7:36

Yeah, we would have.

Jim 7:37

Uh Manchester in England also. We just spent the night transferring between a train and a bus.

Rita 7:41

And we went out that evening walking around and thought, why aren't we staying here longer?

Constraints That Shape Your Style

Jim 7:47

It was a beautiful time. So all kinds of things can happen uh when you're traveling, also, especially the longer the trip, the the more guaranteed you are to have some kind of delays. You know, we've had ferry strikes that changed our plans in Mexico trying to get to Knoxville, and there's a storm in Dallas that interrupts our travel plans.

Rita 8:06

Right. Yeah, we were we were kind of stuck there, but that's almost funny because we we went into the nearest town, which was Corretero, and just fell in love with the little community. So sometimes these little bumps in the road give you an absolute huge opportunity.

Jim 8:23

Yeah, you have to be aware that when you plan any kind of travel, they're going to be problems. And a lot of times it's up to you to turn those problems into a positive experience.

Rita 8:33

Yeah, we've learned to pivot and not get too excited. It always works out.

Jim 8:38

And lastly, you want to think about your general health and mobility issues. And again, that's not a barrier to travel, it's just something you have to consider. Uh, we interviewed a woman who is blind, legally blind, and travels with her seeing eye dog and her husband.

Rita 8:51

Yeah, that was totally interesting.

Jim 8:54

Yeah, they do quite a bit of travel. She's a travel writer and her husband takes pictures.

Rita 8:59

Right. Yeah. And and I thought, well, wow, what does she really enjoy this? But she did.

Jim 9:05

So these are the kind of things that you need to figure out, take an assessment of yourself and decide what kind of travel you can do, what kind of travel you're interested in. So in the book, what we do is break down each type of travel and see what it actually looks like in real life. Now not just the fun parts. We've had some things that weren't quite fun happen while we were traveling. But there are things to consider that we have in the book, like how to handle money overseas. We were quite surprised the last couple of trips, especially that we took to Europe when it came to using cash.

Rita 9:36

Yeah, we hard well, we never took cat yeah, we had a few euros.

Jim 9:40

We would carry some euros with us, but we hardly ever.

Rita 9:42

We it was just your phone, you did the click click and that was it.

Jim 9:46

In fact, we were in the UK for almost a month and never got any British pounds.

Rita 9:51

Right. We didn't.

Jim 9:52

Or one of the things we also look at in the book is what happens when accommodations go sideways.

Rita 9:57

Yes.

Jim 9:58

And we have had that happen on several occasions to varying degrees of severity.

Rita 10:02

We always survive.

Jim 10:04

Yeah, we had that ferry cancellation where we basically were homeless in Greece.

Rita 10:08

Yeah, I hated that.

Jim 10:09

You know, had to find a new place in a hurry.

Rita 10:12

Yeah.

Jim 10:13

Or when we showed up at an Airbnb in Dublin and were told that Airbnbs were illegal in Dublin and they wouldn't let us in.

Rita 10:20

Right. We should have known. It was such a posh area, as they say posh. I mean it was really an upscale area.

Jim 10:27

Now it turns out that they're not exactly illegal in Dublin. They're just very tightly regulated. And this was a case where the tenant who was renting the place was which was against his lease.

Rita 10:40

Yeah.

Jim 10:40

Yeah. And you know, that's not something that they generally put in the ads.

Rita 10:44

No. So we sat on the uh stair stairway and found through booking a hotel, and that was that.

Jim 10:50

That was that, yeah. Now you also need to be dealing with various visa rules. If you're traveling in Europe, you have the Shenzhen limits, and that can get fairly complicated. And even outside the Shenzhen zone, some things can still happen to you. Like when we were going from Thessaloniki in Greece to Istanbul in Turkey, we didn't find out till we were checking in at the airport that we needed an e-visa in order to enter. So we had to jump on our phone sitting at the airport waiting area, log on, fill out some forms, and pay. I think it was about fifty bucks or something like that.

Rita 11:20

Right.

Jim 11:21

Uh to register. So there's a lot of little details that can pop up when you're traveling.

Rita 11:25

It's so nice though. Most of these details you can handle right from your phone. It's just so easy anymore.

Jim 11:32

Yeah, there are a lot of aids and guides to help you do all this, and we outline a lot of those in the book. And in fact, there's an entire chapter just on apps for travel.

Rita 11:40

Right.

Jim 11:40

Now, logistics, dealing with logistics, this kind of leads into the same kind of thing. We'll talk a lot about how you go about planning a trip like this. People often ask, do you plan the travel part first and then look for accommodations? Or do you look for accommodations first and then figure out how you're going to get there? But it's really more of kind of trying to do it all at once.

Rita 11:59

It really is, because you're you're constantly balancing your budget. So if you decide, hey, I can get a cheaper flight to go into Brussels or or Rome, and then you just work from wherever you want to go from there.

Jim 12:16

Yeah, and it's important to remember that wherever you're traveling, especially in Europe, once you get there, it becomes very easy and affordable to get around.

Rita 12:23

Yep. Trains, planes, and automobiles.

Jim 12:28

Yeah, and we will talk about that. And another important issue that we've discovered is health care and insurance.

Rita 12:34

Absolutely.

Jim 12:35

We've run into several instances where we needed health care while on the road. And I really can't say enough about travel insurance.

Staying Flexible When Plans Collapse

Rita 12:42

Right. We've had excellent health care while traveling. We've both had surgeries outside the U.S. Jim was hospitalized for nine days and Riga Latvia. I mean, it just goes on and on, but you can get quality health care no matter where you are.

Jim 12:58

Yeah, and that's again is something we'll come back to time and again. That these are not things that are barriers to travel.

Rita 13:04

No, you just have to be open.

Jim 13:08

Yeah, you have to be aware it can happen, and it's very possible to deal with them while you're traveling.

Rita 13:12

Absolutely.

Jim 13:13

Now a lot of the things in this book come from our own experiences. And you'll hear about the good, the bad, and what we learned the hard way.

Rita 13:20

Aaron Ross Powell Yeah, and some very funny things too.

Jim 13:23

Well sometimes they weren't so funny.

Rita 13:24

Oh. Ended up being funny once we got home.

Jim 13:27

But you really have to laugh.

Rita 13:28

Yeah. Yeah.

Jim 13:29

So for us, these problems are not theoretical. We've done, like Rita said, everything from shorter extended trips to living abroad in Ecuador for several years. And we just tried our little hand at full-time roaming. Every version of those lifestyles comes with trade-offs.

Rita 13:44

They do.

Jim 13:45

So that's what this book is really about, helping you find the travel version that fits your life.

Rita 13:50

And you might really bounce around from different types of travel depending on what suits you at the moment.

Jim 13:57

Right. And you can then figure out your own style or what you want to or what you think will work for you.

Rita 14:02

Right.

Jim 14:03

Now we've had a lot of experiences that you'll read about in this book, and we've had some short trips that went very smoothly.

Rita 14:09

Right.

Jim 14:10

Even on one of our last tours through Europe, our second visit to Prague went very smoothly. We were there for a week, we saw a lot of the town, and we really enjoyed it.

Rita 14:18

Oh, it was lovely.

Jim 14:19

Yeah, when we went to Budapest, we were able to get around Budapest and just had a great time, and we've done a lot of short domestic trips that have also worked out very well. But as I said, we've also had long trips that were interrupted by illness.

Rita 14:32

Right.

Jim 14:33

Just as last time we were in the UK, you had that problem with your it was kind of a sort of a pneumonia, I guess. Right. But we were able to visit several hospitals and clinics throughout the UK. I think we went to two in England and one in Scotland.

Rita 14:45

Yep. Love the AE.

Jim 14:48

We watched enough British shows that when they told us to go to the A and E, we knew what they were talking about.

Rita 14:52

Yeah, thank God for TV.

Jim 14:55

You had a chest x-ray, multiple exams of medication, and it was all free.

Rita 15:00

Right. I mean we we totally expected to pay for my care, and they said no, absolutely not. Not even the prescription.

Jim 15:10

Yeah, or even an x-ray.

Rita 15:11

Right.

Jim 15:12

Not the x ray.

Rita 15:14

Right.

Jim 15:15

And uh there was no fee no fee for that.

Rita 15:17

No.

Jim 15:19

I think one real advantage that we had when it came to trying out long-term travel is that we spent almost six years living in Ecuador.

Rita 15:27

Right. I think that makes um we acclimate very quickly in other countries now.

Money Visas Apps Insurance Basics

Jim 15:33

Yeah, I think the the reality of living in another country and understanding that you don't get to make the rules, you have to live by them.

Rita 15:40

Right, right.

Jim 15:41

It really gave us a heightened comfort level now whenever we go into any country.

Rita 15:44

Aaron Powell Yeah, you're not in Kansas anymore, right?

Jim 15:47

Right. I mean there's there's different cultures, different languages. It really drives home the fact that you're not in control anymore. You're not the most favored citizen anymore.

Rita 15:57

Right.

Jim 15:58

But really you can get to the point where traveling from country to country becomes almost like just traveling from state to state.

Rita 16:04

Aaron Powell It does, especially in the Shenzhen zone, because you don't have passport stamps or anything.

Jim 16:11

And we found that so many people now seem to speak at least a little bit of English.

Rita 16:15

Aaron Ross Powell Oh, yeah, especially the younger kids, if they're in the service industry, absolutely.

Jim 16:21

Yeah, we've met friendly people wherever we've traveled. In Ecuador, we frequented the Mercado all the time. We went shopping in La Libertad district where you hardly ever saw any other gringos.

Rita 16:31

Aaron Powell Right. We had an egg person, a veggie lady, a chicken marry. Yeah, we made buddies in the mercado.

Jim 16:38

Yeah, my friend the fish guys, they love me.

Rita 16:40

Oh yeah, they did.

Jim 16:41

Yeah. And we love going to markets no matter what country we're in. Partly because it's such a wholesome experience, but also because that's where the people are. That's where the real people are.

Rita 16:50

Right. Right. You can you can see how the everyday man lives.

Jim 16:54

Yeah, you'll read a lot about that in the book. We're really a sucker for those markets.

Rita 16:58

Oh, yeah.

Jim 16:59

I mean, even not just the little local markets, even things like Spice Market and the Egyptian Bazaar in Istanbul.

Rita 17:05

Right. And and we travel light. So going to these markets is not it it's usually to buy food because we're in condos or whatever, but we're and we travel light. We don't buy things to bring it home. And if we did, we'd have it shipped. But mainly we're there to see how people live.

Jim 17:23

Right. And you'll learn as we go through parts of the book here, if you pick up the book yourself, which we certainly hope you'll do, you'll learn that a lot of the strategies for keeping your costs down on long-term travel is being able to have a kitchen and being able to do simple things like have breakfast in your own place or be able to have lunch somewhere and bring back leftovers to eat later.

Rita 17:42

Right. Right.

Jim 17:43

I mean, breakfast in a lot of places going to cost you $25 to $40. You can end up spending more on meals and restaurants than you do on lodging.

Rita 17:51

Right. And and it's really nice that when you wake up, you can have your coffee. Because I'm a sucker for coffee. I have to have that coffee before I leave my condo.

Jim 18:01

Yeah, that's one of the nice things we found about just about every place in Europe. Almost all of them at least have a kettle.

Rita 18:07

Right.

Jim 18:07

So you can get up and make your coffee in the morning before you leave the room.

Rita 18:10

Right. We we travel with coffee and our luggage. And yeah.

Jim 18:15

I think the little place in Kenber was the only place where the coffee was downstairs.

Rita 18:20

Yeah, that didn't stop me though. I went right down there in my pajamas and got it.

Jim 18:25

Now another thing we've had a lot of personal experience with is working while on the road. You know, we talked about New Orleans, things like that, and you mentioned Italy and some of the places we've been. But when we first moved to Ecuador, I was still working as well.

Rita 18:38

Right.

Jim 18:38

So I spent a y a year and a half or so, two years maybe working remotely. And really even now while we're traveling, if we're recording podcasts, if I'm writing for international living or some other venue, we're actually still doing the digital nomad thing.

Rita 18:53

Right.

Jim 18:53

Yeah, we're still doing some work of some kind. So that's what I mean about these types of travel sometimes overlapping.

Rita 18:59

They do.

Jim 19:00

And it's important to try to maintain a balance, especially if you're working. We'll talk about this more in the digital nomad episode, but i in Ecuador I was working a lot, something like forty or fifty hours a week sometimes. And all the time I'm working, I've got, you know, two computer screens up and I'm working on five or six computers at the same time in different parts of the U.S. And I can hear people out on the beach laughing and falling off the banana boats and vendors going by and everybody having a wonderful time, and I'm sitting in there working. So it's it's tough to find a life balance sometimes if you're working abroad. And we'll talk more about that when we uh get into that digital nomad scene.

Rita 19:36

Yeah, that's when we you were working though really full time.

Jim 19:40

Yeah.

Rita 19:40

Yeah.

Jim 19:41

So what we're saying is that if you've ever thought about traveling longer but weren't sure how to make it work, this book will walk you through it. Now it's called Wherever We May Roam, Finding Your Travel Style, and it's available now on Amazon. And if you do check it out, I'd really appreciate a quick review. It really helps more people find the book. It's been fun being back behind the mic again, too, hasn't it, Rita?

Rita 20:02

Oh yeah, great.

Jim 20:04

In the next episode, we'll go into more detail about the easiest way to get started on a roaming lifestyle, the extended getaways. And in the future, we'll also be interviewing other travelers and checking in with some old friends of the podcast out on the road. So until next time, 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 discuss, or would like to be on our show, email us at Jim at Jim SantosBooks.com. Thanks for listening, and as always, safe travels wherever you may roam.