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
AI Travel Planning That Actually Saves Time
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Weeks of travel planning can come down to one stubborn problem: turning a big dream into a realistic route that fits your time, energy, budget, and check-in times. We’re Jim and Rita Santos, and we’ve built plenty of complicated itineraries the old-fashioned way with spreadsheets, tabs, and too many “wait, what day do we check out?” mistakes. This time, we try something different: we hand AI a tight set of rules and see if it can draft a trip that actually matches our travel style.
We walk through a 53-day Europe overland itinerary starting in Madrid and ending in Hamburg, using trains, buses, and ferries with ride times capped at about six and a half hours. AI spits out a full outline in about 87 seconds, then surprises us with extra travel research like top highlights, typical weather, and the big “book early” reminders that can make or break a trip (Anne Frank House, Sagrada Familia, Louvre timed entry, tulip season tickets). We also share where we still tweak the plan, like cutting expensive stays and avoiding too many two-night stops.
Then we run a smaller experiment: a senior-friendly 2–3 night getaway within a 5.5-hour drive from Knoxville that avoids heavy crowds. The results are genuinely useful, but we also talk about the fine print: AI can be wrong, schedules change, and personalization can feel both exciting and a little unsettling. If you’re curious about AI travel planning, Europe train travel, or just traveling smarter, hit play, then subscribe, share the show with a travel buddy, and leave a quick review so more listeners can find us.
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"Wherever We May Roam: Finding Your Travel Style" - On Amazon
Big Trips And Real Constraints
JimWhat if I told you we planned a 53-day trip, hitting 15 cities and four countries in Europe, and the hardest part only took a few minutes. 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. Welcome everybody to Wherever We May Roam. I'm Jim Santos alongside my wife and travel companion Rita. If you followed our podcast and books, you know that Rita and I have planned several rather complicated and extended trips. For instance, our last trip to Europe started in March in Portugal and Spain, had us in UK for almost a month, and then a month touring through Ireland. The hardest part of planning these trips is figuring where we want to go and how much time we need to spend there. It's complicated by how long does it take to get there and what's the best mode of travel.
RitaWe prefer to, of course, we have the major flight over to get to Europe, but we prefer from there on out to do trains or buses so that we can actually see the countries and not waste so much time waiting around in an airport. You know, you have to be there two hours early, et cetera, et cetera. And most of those airports are an hour or so away from the major cities that we're going to. So then you have that to get that transportation to deal with to get to our lodging in whatever city we're staying. So yes, our overland part is by train and bus.
JimYeah. And part of the complications, well, we go into more detail in this in the book, Wherever We May Roam, uh finding your travel style. Another complication is most of the time, whether it's hotel or an AB or Airbnb, you can't check in until two o'clock or later.
Speaker 2Right.
JimAnd you have to check out by 10 or 11 a.m.
SpeakerYes.
JimSo flight times especially are not always really conducive for that. But with buses and trains, there are generally several options. So you can kind of pick the time that you leave and the time that you get there. That also affects how much time you can spend getting from place to place.
RitaRight. And you have to set parameters there too. You don't want to be on a bus or a plane all day.
JimRight. So what we usually do is we start with the fur the two big steps, getting to Europe and getting back from Europe.
RitaExactly.
JimSo once we have the dates and the locations where we're going to be doing that, then it's well, what do we want to see in between? You know, set up spreadsheets, spend a lot of time uh researching what's to do in the area, then looking at bus schedules, train schedules, and everything, figuring out how to get back and forth uh between those. It really takes a long time to do all that. And it involves a lot of work.
RitaIt really, Jim does the the the high percentage of this, and it takes him weeks to sort that out.
JimYeah, and then there's usually some mistake you made and you've got to go back and reschedule. Yeah, a common thing is say you're going to spend three nights in someplace. It's easy to make a mistake on which day you check in, and then three nights later which day you check out.
Speaker 2Right.
JimBecause the same day you're checking out, you're generally checking in to something else. And it's easy to make a mistake in there, and then you've got this cascading problem where you've got the wrong dates for everything.
RitaAnd and we don't do our travels set in stone because you have to you might get sick, you might be tired, you have to just pivot as you go. So we don't set every little stop in stone until we're pretty much ready to be there.
Why Trains Beat Airports
JimYeah, so now that we set the general scene for you there of what we've been doing, let's let's talk a little bit about AI and how that's been creeping into travel lately. You may have noticed even if you do a Google search now, just a regular Google search, there's a little box that pops up and you see it run through uh the logos of like YouTube and CNN or just a bunch of little logos as it goes through and searches some things on the web and then puts up the information that it thinks you want to look at. That's kind of a little primitive AI thing that Google is using uh to try to help you do searches. So that that's been going for a while, and you're probably not even aware that that's been going on. There have also been things like the latest updates in Alexa. We we have a smart Alexa and a dumb Alexa.
RitaAnd the dumb Alexa drives us crazy.
JimYeah, the the dumb one, you ask it for the weather and you get a pretty cut-and-dried weather report. But the other one you ask it and it's got a little personality and it'll give you a little more information, maybe tell you what the temperature feels like.
Speaker 2Right.
JimSo it's a little more detailed, and this has been creeping up slower and slower. Then there are also things like on Google Flights, you can set flight alerts. You can have little bots that are searching for the best deal and sending you information on that. So it's not like there's been an overnight change, but it's been kind of creeping up on us through here. Lately we've been experimenting a lot with with AI tools uh for planning and and also for research. So I thought when we sat down for this trip, we had decided that we were going to go back to Europe. Uh we wanted to leave uh sometime in March, go through parts of Spain, France, and gradually work our way to Hamburg and Germany and end up in Copenhagen because we had booked Nordic cruise leaving Copenhagen at a certain date. So we thought we'd get to Europe early, we'll explore Europe some, then we'll get on this cruise and then we'll come home. So sounds simple. It's it's almost 90 days of travel.
RitaRight. And actually the cruise is pretty simple. You hit all the Scandinavian countries and Iceland.
JimYeah, the cruise is almost a third of the 28 days or whatever.
RitaAnd Estonia, it hits Estonia too.
JimRight. But we figured if we wanted to spend some time in Copenhagen before the the cruise, we had roughly 53 days between arriving in Madrid and getting to Hamburg, Germany, so that we could go uh short train or or bus from Hamburg into Copenhagen for a few days and do our cruise. So it's 53 days overland through Europe.
RitaRight.
JimAnd I shuddered to think about trying to plan all that out.
RitaMe too. Because we're, I mean, we're going we're gonna try to go to Amsterdam and see the tulips during that season. Yeah, it was getting a little complicated.
JimYeah, and by the way, a quick flashback to the last episode where we talked about credit cards and travel and points. We have booked our flights now, one-way trips from Knoxville to Madrid.
Speaker 2Yeah.
JimAnd uh using points from our MX card, we paid a grand total of $64 and 64 cents.
Speaker 2Woo-woo!
JimThat's the total for the two of us, and includes baggage and taxes and everything. So that's a nice little budget cut right there.
AI Enters The Planning Workflow
RitaI love those points.
JimAll right, so back to the uh AI thing. So what it decided to do was ask AI to plan out a basic Europe overland itinerary for us. If you've never used AI before, the the best way to get the most out of it is to make sure that you set the parameters correctly.
RitaRight.
JimBecause it is very literal. So you have to be careful the way you you phrase things.
RitaAnd we have been traveling so much we do have parameters of what we will accept.
JimSo what we told it is we wanted a possible travel itinerary for Europe using these parameters. Number one, use bus, train, or ferry to move from city to city. Number two, trip duration between cities less than six and a half hours. We we find that's about our our limit on the price.
RitaOh yeah, that's it. Yeah, we're done.
JimThe trip would begin in Madrid, Spain, early morning, March twenty-fifth, twenty twenty-seven, so we gave it a definite date and location where it would start, and ends in Hamburg, Germany, May 17th or 18th, 2027. Then we told it the stops to include in this order Madrid, Alicante, Benedorm, Valencia, and Barcelona in Spain, then Toulouse, Marseille, Lyon, Paris, and Lille in France, Ghent in Belgium, Rotterdam and Amsterdam in the Netherlands, Bremen and Hamburg in Germany. So like I said, it's quite a trip.
RitaYeah, it's quite a mix. Oh, okay. Yeah. And and we don't mind using trains if they're shorter. Yeah and if they it depends on really it's it's economics, w which one can get us there, which one is cheaper. It just depends on how you want to go.
JimAnd time if if the if the bus is eight hours and the train is three and a half.
RitaOh, we're doing the three and a half. Yeah, that's it.
JimAll right. So now that I laid out those parameters for it, I asked it to suggest the length of stay in each city based on the total trip time and things to see in each city. And then just to see what it said, I also suggested give us alternatives if a different stop is recommended. Also any possible day trips or overnights, like maybe going to Geneva when we're in Lyon, something like that. So I put that in, hit enter, and it took a total of, let me see here. Okay, it took it a total of one minute and twenty-seven seconds.
RitaWow. Wow.
JimTo spit out a Europe overland itinerary, Madrid to Hamburg, March 25th to May 17th, 53 nights, bus, train, and ferry.
RitaNow, this is something that we have to tweak, but it was definitely a good outline.
JimYeah, that when we looked it over, we decided, well, it was giving us nine nights in Paris. Paris is a pretty expensive place to stay, so we decided we'd cut that a little bit.
RitaYeah, we'd cut it.
JimAlso, it gave us several places where we were just staying two nights, but we find you really need three nights because the first day you're first night you just got there. Second, yeah, you know, just one night. Yeah, right.
RitaYeah.
JimSo we did a little altering on that schedule a little bit, but still it saved us an incredible amount of time.
RitaRight. And and it did have some good ideas about like in Lyon to go to Geneva, but we said maybe we go to Anasi instead.
JimWe haven't totally Yeah, it gave us two possible side trips, Geneva and Anasi. Um, recommending Anasi as maybe a lower cost trip and just as much scenic beauty.
RitaRight.
JimThe other thing it did that I didn't expect was it gave us top highlights in each city.
RitaIt did, yeah.
JimA list of possible places to see and things to do while we're in the area, and even some possible day trips that are just outside the area, like in in Madrid. It suggested uh that we could take an hour bus ride to Segovia, which another person we interviewed also mentioned as a beautiful place in Spain. The Alcazar Castle is supposed to be what inspired Disney's uh Cinderella Castle.
RitaWell, that's cool.
JimSo, you know, that might be interesting. And then it gave us things like the the typical weather in the area for those dates. And if there was anything that we really wanted to see, if early ticket purchase was recommended. It told us about that. Right. This is a big deal in Barcelona. If you want to see the uh the big cathedral, you have to book that pretty early.
RitaAnd and the tulip.
JimYeah, it also told congratulated us on our timing because when we're in Amsterdam, we're right at peak tulip season.
RitaRight.
JimSo it recommended that we get tickets for that six months in advance.
RitaSix months in advance. Yeah.
JimSo there was a lot of very useful information that would normally take us just days and days to sort of to assemble and sort through and figure out. And it'll still take some time.
Building The 53-Day Europe Route
JimI mean, it spit up a lot of possibilities.
RitaRight. And it's not and and it's not like everything is set in stone. Like when we went to Portugal last year, we were we were in our lodging and we said, wow, Seville is just an hour's bus ride away. So we said, hey, let's do that. And we spent five days in Seville.
JimAnd like $14 each to get there. Right.
RitaSo why so yeah, so voila, that was cool.
JimYeah, so it gave us some route notes and transportation trips tips also, which I didn't ask for. Uh, mentioned the Sogarata Familia. If you want to see that, you have to. It gave us the website to book it at and told us it should be, you know, a certain amount of time ahead of time. If you want to see the Anne Frank House in Amsterdam, that's another one you have to to book quickly. The Louvre also has timed entry only. And that's another thing. If you want to get in there, you've got to get online and get your passes early. Now, naturally, it couldn't give us that far in advance, it couldn't give us specific bus and train times.
Speaker 2No.
JimBut it did tell us which buses and trains serviced each area and the approximate transit time. But when I did ask specific information, like getting from Hamburg to Copenhagen, we had been assuming that we would fly.
RitaYeah, we did.
JimBut when I started looking at flights, the one-way flight for two was two hundred dollars. I thought, well, that's not horrible. It's only an hour flight.
Speaker 2Right.
JimBut then when I looked at the I Icelantic era to to book it, it said that, well, then also there's a fee for your your check bag, there's a fee for your carry-on bag, there's a fee for seat selection.
unknownYeah.
JimSo it rapidly got up to like $350 for the two of us. So I asked it about getting to uh between Hamburg and Copenhagen by bus or train. And it did tell us that you could get the train for as little as twenty-eight dollars each.
RitaThat's cool.
JimIf you booked it six months in advance.
RitaOh.
JimAnd offered to put a note in my calendar for when to go to look to order the uh the tickets.
Speaker 2All right.
JimAnd when I checked my calendar, the note was there along with a link to the uh train company.
Speaker 2Oh.
JimSome really helpful information came from that. Now I I do have to say though, you have to be careful. Anytime you do any search on AI for anything, right at the bottom it'll tell you AI can make mistakes. Please double check responses. And I mentioned it can also be very literal sometimes. And and that's easy to forget because it gets almost chatty with you.
SpeakerYeah.
JimThe more you use it, the more it it kind of personalizes it to yourself.
RitaIt's but but years ago we had train tickets that were going to drop us off in Barcelona, I think, and the airline never told us that they had canceled that flight.
JimSo Yeah, it was a flight from Dubrovnik and Dubrovisha to Barcelona.
RitaYeah, and they canceled it, no notice to us. We would have gone to
What AI Adds Beyond Dates
Ritathe airport and of course not had a flight. So you always have to keep tabs of everything when you're traveling.
JimYeah, and of course, the travel times it gives are estimates. They're not live schedules. You you don't know about you know wildfires in the area or exactly when we went from Athens to Thessalonia.
SpeakerThessaloniki.
JimThessaloniki. I'm sorry. We were originally planning on going by train, but then we found out there were wildfires between us and Thessaloniki. So instead of taking a train or a bus, we flew there. So things are going to change a little bit, especially when you're planning that far ahead. Timetables and schedules may not even be released yet for that. Right. So consider the AI's output as a very well-informed starting point.
Speaker 2Right.
JimBut not a booking ready document. Yeah, especially travel connections. Yeah. Yeah, you need to check those. Those must-book in advance options are very useful as well.
Speaker 2Yeah.
JimAnd it also gave us some practical information. Like I think it was in Valencia, which is famous for his paella.
RitaOh, yeah, that's right. Yeah.
JimIt warned us that paella is served for lunch, not for dinner.
RitaRight.
JimAnd you really look like a tourist if you try to get it for dinner.
RitaRight. Yeah. And Jim makes paella, so we're definitely having paella.
JimBut we make it for dinner. We do. Yeah. We would have been ignorant of that fact.
RitaBut they they have their lunch late and their dinner super late, like 10.
JimYeah, we've run into that especially in Buenos Aires.
RitaBuenos Aires was like that.
JimYeah, we were coming back from Tango Show and Dinner.
RitaRight.
JimAnd it was after midnight.
RitaIt was.
JimAnd the restaurants were just packed.
RitaYeah. People were having their supper. Yeah.
JimAnd the the driver told us, Oh, yeah, thanks for just getting started.
RitaYeah.
JimSo now I recognize not everybody needs to plan a 53-day 15 uh stop trip through Europe. So I wanted to look at a more modest trip. So let's do a little experiment here and got my little AI tool open. And just gonna ask it to suggest a two or three night getaway for two seniors, no more than five and a half hour drive from Knoxville, and not too crowded. And it can be weekdays or weekends, because we're retired. So let me hit enter here. And first of all, it's showing me all of the reasoning. I don't know if you can see that, Rita, but it's telling me the reasoning is kind of restating what I told it.
SpeakerOkay.
JimAnd now it's doing web searches. You see little things pop up as it's looking at Facebook and Southern Living, looking on Reddit. It's doing several red searches, uh looking, gathering information about the area and the trip. See, that part took it 18 and a half seconds. The next web search for ways to travel and travel times took a little longer. That was 39.7 seconds.
RitaWe are getting spoiled with this.
JimSo less than a minute after asking it that came up with four recommendations.
RitaOkay.
JimIts top recommendations was Highlands, North Carolina, about two and a two and three quarter hours to three hours away. Cool climate, mountain town, 4,100 feet elevation, favored by older, low-key crowds rather than the Gatlinburg style tourist rush.
RitaThat sounds like us.
JimYeah. Says flat, walkable main street with upscale but easy shopping and dining, no big attractions pulling in crowds or lines. It also goes on then to list some sites in the area, some falls, places that you can stay, and a possible day trip into Cashiers, North Carolina.
RitaOh, yeah.
JimI was also amused to see it offered us Berkeley Springs, West Virginia.
RitaWow.
JimUsed to be about what forty-five minutes from where we lived. Calling it a historic mineral spa town, but it was just outside of our limit. So it just threw it out as an option if we wanted to go a little bit further.
Speaker 2Right.
JimBut then went with Blue Ridge, Georgia, which is a mountain town on a river, again, about two and a half, three hours away. Easily manageable on foot, calmer than the Blue Ridge, Georgia's cousin towns like Helen, which we visited.
RitaWhich we have, yeah.
JimAnd is really touristy.
RitaOh, it was. It it's it was sweet. It mu like a mocking village. Yeah.
JimYeah, with fake German food.
RitaYeah, yeah, the food was yeah, exactly.
JimBut Blue Ridge might be attractive because there's a scenic railway ride. Told us about that, and the weekends pick up, but it's nothing like the Gatlinburg thing, which we avoid like the plague, really.
Speaker 2Right.
JimUh you can get riverside cabins there, and it recommended a couple other places where there are no stairs. So again, it's it's keeping in mind that you're asking it for senior travel.
RitaYeah, that those are all good options.
JimAnd lastly, it suggested Abingdon, Virginia, uh, which we pass on the way to visit our kids. It's about three, three and a half hours from here. Also says it has a walkable historic district, the Barter Theater, the Virginia Creeper Trail is there where you can take a nice scenic walk, and again offered places to stay and some places you might want to eat while you're in town.
RitaOh, that's cool.
JimYeah. And then it gave it its main recommendation. It went with the Highlands, North Carolina for three nights on a weekend.
RitaI think that's on a weekend. Or on a week.
JimI'm sorry, on a weekday. Oh, okay.
RitaThree weekdays.
JimThree weekdays. So it's the shortest drive, well within our parameters, cooler mountain air, and older,
A Quick Getaway Test Run
Jimquieter visitor demographic.
RitaThat sounds like us.
JimYeah. So it sounded very interesting. Then it also offered to check specific lodging availability or to draft a day-by-day itinerary for the Highlands. So I said, sure, why not?
RitaYeah. Yeah. We're easy.
JimAnd it came up with some rather pricey lodgings. We were able to find some cheaper things on booking and Airbnb. But again, we're not relying on it completely. We're just using it.
SpeakerExactly.
JimWe never would have thought of Highlands North Carolina. We didn't know it existed.
SpeakerNo.
JimYeah. So that was a great thing to throw at us here. But then it does go into a day-by-day itinerary, suggests some things that you can do in and around the area, even suggests some places to try to eat, and we'll let recommends where you might need a reservation to eat there, even and even though it's more uncrowded. And then even offer to provide a packing list.
RitaOkay.
JimOr give us a quick podcast note so we can do a podcast about the trip when we get back.
RitaSo interesting.
JimWhich is interesting because it knows we do a podcast.
RitaYes.
JimIt's researched us enough to know that. It knows that we have some travel books.
RitaAnd you didn't tell them that. No, I didn't specifically.
JimBut because we've been using it for research and things like that, it's been storing little bits of information about us. So it's the kind of thing that the more you use it, the more use that you're going to get out of it. So it's a brave new world and kind of I'm excited about it. Yeah. It's exciting and and borderline frightening.
RitaWell, yeah, yeah, but it knows us so well. Yeah. But it saves us a huge amount of effort and time.
JimYeah, the amount of time it would take to go through and try to pick that, looking at maps and you know, looking at the information about the different sites and trying to get an idea of what kind of crowds they have and when they have it can just take hours and hours.
RitaYeah, because we don't travel in high season anywhere. And the fact that it it now tells you anticipated crowd size.
JimYeah, so we have found it very useful. I think we'll find it even more useful uh as we go on here. And as we continue to plan for that spring trip,
Trust But Verify Plus Wrap-Up
Jimwe'll keep you up to date with how much we've been using these kind of new tools uh to plan the travel or to help uh plan the travel and maybe some tips on how to use it best.
Speaker 2Right.
JimNow that's all for this week. If you have any questions, please email us at jim@jimsantosbooks.com or leave a note on the podcast page. Next week we'll be speaking with Madison Rolley, a creator and entrepreneurial leading voice at the intersection of travel and technology. She'll expand on how AI and other new resources are changing the way we travel and talk about finding the best travel deals. Until then, 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@Jim Santosbooks.com. Thanks for listening, and as always, safe travels wherever you may roam.
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