The World Nomads Podcast: Traveling with Children

In this episode, the couple exploring the world one country at a time, encouraging their kids to embrace life and create memories.


family scuba diving Photo © Supplied

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The World Nomads Podcast: Traveling during COVID-19

With COVID-19 still affecting the way we engage with the world, it’s important to plan wisely and travel responsibly, both for your own safety and that of the places you visit. But as we reengage with the world, you're likely planning vacations not far from home. World Nomads can help by providing travel safety tips, inspiring content, and travel insurance designed to protect you while traveling.

Before you buy a travel insurance policy, check your government travel warnings and health advice – there may be no travel insurance cover for locations with a government travel ban or health advice against travel.

What's in the episode

00:29 Carving out a way of life

03:20 Finding a project

05:38 Jessica’s fears

09:04 Sunsets and sunrises

12:30 Why its great to travel as a family

16:00 The pros and cons

19:05 Time to confess

23:13 Learning something new

26:44 Travel insurance message

Quotes from the episode

The only reason why we're here right now is because of the kids. Now granted we wanted this anyway, but there was no greater spark that ignited this flame other than the kids.” – Will

And part of the reason kind of going out into the world besides like Will said, we did this because of them. We wanted them to learn about the world in the world. We wanted to live more minimalist. We wanted to create memories over buying stuff. We wanted to show them life outside of even our home in Massachusetts.” - Jessica

Who's on the show

Will and Jessica, together with their 2 children, have been traveling the world full-time for 6 years. What originally begun as a way to create a deeper bond as a family, grew into a philosophy and a way of life, all of which they share on their YouTube channel.

WorldTowning as a philosophy is the act of taking up temporary residence in foreign places, to experience day-to-day life as a local. 

In 2019, WorldTowning also became a family-run travel company, committed to helping people broaden their global experiences through concentrated and immersive exposures to the world’s cultures. The family offers small groups of travelers, the opportunity to embark on shared experiences and adventures, in order to live the world as locals. 

However, in March 2020, Covid-19 brought their business to a halt. So, what did this family decide to do? They bought a yacht…

Follow their adventure on Facebook and Instagram.

family hugging
Will and Jessica have been traveling with their children for six years

Links and resources

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We use the Rodecaster Pro to record our episodes and interviews when in the studio, made possible with the kind support of Rode.

Kim: Hi and thanks for tuning in from wherever you get your favorite pods as we dip our toes into the world of travel with children, some say its impossible others will say it’s hard work but this couple will hopefully change your mind. Will and Jessica, together with their 2 children, have been traveling the world full-time for 6 years. Originally it began as a way to create a deeper bond as a family, but it quickly grew into a way of life and, also a business.

Jessica: So Kim, thank you so much for having us today. We are a family of four, two adults and two teenagers. We have a 13-year-old son and a 16 year old daughter. We are Americans. We had lived all over the United States until 2014, and at 2014, we made a decision... well, we made a decision before that. But in 2014, we launched from Boston, Massachusetts to go and live one year in Costa Rica.

Jessica: We were telling everyone it was going to be one year, but the plan was for as long as the family and our finances could sustain it. And now we are in 2020 and we are still out here traveling. So that one year plan did manifest into being more and a lifestyle choice. And in the meantime, we have spent a year in Costa Rica, a year in Ecuador, a year in the South of France living as locals, among locals in an apartment. After we were done living in France, we bought an RV and we traveled around Europe for two and a half years in 21 and a half feet, or just under... was it just under six meters, Will? Just under-

Will: Around there.

Jessica: Just under six meters, with a goal to see Europe on kind of on a more grassroots level, and also to visit every country in Europe. So we accomplished that goal, as well as spent some time in Morocco and some time in the non-European side of Turkey. And after that, we decided we were going to head to Asia for one year and we were going to spend a month in 12 different countries, and each family got to pick the three countries that they wanted to go visit. And that plan was going smashingly well. We went there, we started off in Japan. And then the numbers in COVID kind of started to rise and things got more serious and places started to lock down and we ended up being in Japan for five months.

Jessica: And after that, we kind of looked at our life and said, okay, this Asian tour isn't really going to be how we wanted it to be. And we don't really fancy spending five or six months in one country, five or six months in another country, and that being kind of the cumulation of our Asian experience. We wanted something a little deeper and a little more diverse. So as a family, we made a decision that we believed COVID wasn't going to go away overnight and we had to figure out what the next step would be in the process. And we felt that for our family, that it was best that we didn't try to continue and find countries that were open, that we felt that this was serious and we needed to take it serious and we wanted to be safe for ourselves and for others.

Jessica: So we decided, our 16 year old daughter said, "Well, we're not going to do so well if we just go sit in an apartment someplace after traveling like this for six years, we need a project." And so Will and I said, "Okay, well let's do this." Will and I in our previous life did a lot of buying and remodeling in real estate, but the kids hadn't had the experience of learning how to do this. So we said let's buy a little house in France, a fixer. We have French long stay visas so we can legally come back and live here. And this will kind of hold us through COVID. And once COVID has done, we'll get back on the road and travel. And that was the plan. When we left Japan, we had appointments to look at three or four houses when we got here in the first week, excuse me. And on my Facebook feed here comes a cute little boat comes across... no, not little, but a cute boat comes across my feed. And I say to Will, "Wow Will, look at this."

Jessica: And just a little backstory there, our end game, or our plan after Asia was to get on a boat. That was always one of our dreams and goals. But we hadn't really planned on doing it before Asia because we realized once we got on a boat and started traveling, it's kind of expensive, pull it out of the water and start traveling by land again. So we kind of wanted to finish a lot of the land adventures we had planned. And long story short, that boat, we took a look at it and that boat was a really, really good deal. And it was in France already, and it needed very little work and it came with a six month slip so we could stay at the slip and learn to sail and kind of work our way through COVID. So long story short, here we are, in the South of France, on a boat. We don't know how to sail. And now we've got the boat, but lockdown here in France happened before we could get the lessons so we're not moving any place right now, but we're learning the mechanics of it.

Kim: See, what I like about you, Jessica, and obviously you too, Will, because you need to be like-minded people to do this, we, my husband and I love travel, and we also love real estate. And like you have bought and renovated places. And as we traverse Australia, we keep finding these cute little Outback towns and really cheap little sandstone cottages that we can do up and stay-

Jessica: Right?

Kim: So you say you've got an end game, but before the end game, things just change. And I think that's really cool.

Jessica: Yeah. It's interesting because I'm going to be honest, I was the most resistant to getting on a sailboat. It scares the heck out of me. And 2020 has been a lot of me fighting fears. I don't have a lot of fears, but the bigger ones seem to all culminate in 2020 and I had to face them. And I wasn't really into getting on the sailboat yet. I felt like we have a huge learning curve. I felt like we had to read books for years and years and years before we even stepped foot on a sailboat. So it just ended up being that it was the best decision. And I jumped in and I said, "Okay, I'm going to do this." But I'm still a little scared. I'm not going to deny that I'm not scared, but sometimes we just have to take that plunge, right, and jump in before we're fully ready. We're clearly going to get educated and read the books and take the sailing lessons before we take off and obviously do a crossing or something like that. Right Will?

Will: Listen, we'd love, like you said, Kim, we love the idea of real estate and we've been sort of trying to sort of amass a portfolio of different properties and then sort of slowly divest it as you sort of more working capital to sort of keep your life the way that you really want it to be. And that's okay because you work for a reason, to actually enjoy the fruits of your labor.

Will: But when we decided to make this decision, the other issue was that our children are only going to be around us for so long. And if we just got a house, that'd be great, but we wouldn't have this massive adventure of sort of learning how to sail as a family. And we wouldn't be able to... I guess, because now Jessica and I are not in our thirties anymore. So I feel like we also need them as crew to help us make this [inaudible 00:06:37] work out well. So I don't think that we'll ever sort of stop loving sort of the buying of houses and rehabbing and so forth and so on, but right now, this is the perfect time for us.

Jessica: Yeah. I think this is where we need to be right now. And it's funny because I'm the one who shared the boat image with Will and said, "Should we look at this?" So I, as I was saying, was the least on board, but I am the one who kind of put it out there. And I knew once I put it out there, Will would be like, "Hell yeah, let's do it." Now that I look back on it, it was kind of tough. Like, do we buy the house or do we buy the boat? We were toying with both. And now I'm not even thinking about the house.

Jessica: I think about what you said, like, "Oh, look at that little cottage and I could do this and that and that sounds really fun and wow, that's a great deal." Because there's tons of great deals in France in these more rural areas. But then I also think about what we would have gained from each one of them. And I think the family unity and learning together, and the intense experiences are far greater on the boat than they would be in the house. I can't say for sure because I've never done a boat before, but we've done a house remodel before and you kind of, you remodel it and then it's done. Right? And the boat, it's just kind of endless.

Kim: Yeah. What I like about you guys being on a boat too, as opposed to a house, and this is something that I wrote about today, is that I've seen sunsets, I've seen sunrises obviously. But only if I take myself off my couch to see the sunset or get myself out of bed to see the sunrise. But in the short time that we've been on the road, every sunrise we've captured, it's been different. Every sunset we've captured has been different. And last night there was a sensational light show across South Australia or Adelaide in Pacific... pacifically? Specifically where I am, 100,000 lightning strikes. Now we would never have seen that if we were sitting inside our lounge room. You just wouldn't do it. So you guys on a boat, think of the moons that you're going to see. Some of the fish that will be swimming around, the color of the water, the bio-luminescence, there are going to be so many experiences that you probably couldn't have even listed that you'll feel or see. Did that sound like I was preaching?

Will: Yeah, we're so excited about that.

Jessica: No, no.

Will: No, you're absolutely right. And we also did a van life experience for two and a half years. There were some moments where, you know how it is, you're driving around looking for a place to sort of stop for the night and it's dark. And next thing you know, you don't know what you're going to wake up to. And then when that sunrises you're just like, oh my gosh, look what I just did. And look where I just landed. There were moments when we were in Norway-

Jessica: I knew you were going to say Norway. I was like, all that was going through my head is Norway Norway Norway.

Will: Which we hear is the most magnificent place to van life in the world [inaudible 00:09:30] New Zealand. We've never done New Zealand, but we've heard great things about New Zealand. But the things that we witnessed and the things that we sort of stopped at and woke up to were just, they blew us away. And there's no way this would be possible unless you just threw caution to the wind and said, "I'm going to do this." And come what may, it doesn't matter. Because at the end of the day, you don't really care about what you have in the grave with you. You care about what's in your heart, in your spirit that you've accumulated along the way. And we're trying to sort of make that happen. And we know that no matter what happens, you come with a good intention, good things will happen. We're just sort of seizing every moment that we can.

Jessica: I think it was funny that you're mentioning sunrises and sunsets and moons. We haven't even left the dock and Will will wake me up in the morning and say, "Come look at the fog, look at how the fog is rising." Or we have magnificent sunsets here. And like I said, we haven't left the dock. If this is just scratching the surface of what we're going to see, and we have boats all around us and there's some condos here, what is it going to be like when we're out there and there's crystal clear water and sunsets and sunrises and no one else around? And we're just like... jaw dropping stuff. Like in Norway, just looking up and going, "Wow, look at all the stars."

Kim: Yeah. My mind has been blown at the things that I've obviously seen over the years, but to pack them into such a short period of time has been incredible. And by the way, you will love New Zealand and RV-ing there. Jessica and Will, I want to chat about your kids because we aren't traveling with children. Had you not done this experience with them, this is a long-winded way of asking you this, but I think you would be feeling happy that you're influencing the type of adults that they will become based on the experiences that they're having. As opposed to being in a town with a house and a traditional routine as such.

Will: Right. That is sort of the impetus of why we did this. The only reason why we're here right now is because of the kids. Now granted we wanted this anyway, but there was no greater spark that ignited this flame other than the kids. And when the kids were... our eldest daughter was in the fourth grade and our son was in first grade. And we started to see certain things occur. We started to see our daughter... Because girls when they reach nine, 10 years old, social norms start becoming a big thing. Before that, kids are just kids and they say what's on their mind and life is grand. But when you start seeing this age occurred, you start seeing cliques occur, you start seeing groupthink occur, you start seeing things that would inhibit someone's natural progress occurring. We said at that moment that if we don't move now, that her personality would not be shaped by who she is, but by who she's around. And the idea of her not being able to naturally explore who she wants to be because she's worried about what someone else might think really, really, really just concerned us.

Jessica: That was really scary, very, very scary. And I think to kind of take it in a different direction... Because that, that was something Will really felt passionate about. And I agreed with him, but he was more in shock of it. He grew up, there were three boys and he hadn't seen kind of this behavior before. Boys have a whole other set of kind of conforming to the norms. I was less shocked than that, but that didn't mean I accepted it. And part of the reason kind of going out into the world besides like Will said, we did this because of them. We wanted them to learn about the world in the world. We wanted to live more minimalist. We wanted to create memories over buying stuff. We wanted to show them life outside of even our home in Massachusetts. Life outside of Will was an accountant, I was a graphic designer. We had this house, these are the things we liked.

Jessica: Because the idea is not to raise mini mes. The idea is like Will said, to let them find their authentic self and become their authentic self. And if they are only exposed in their entire childhood to Will and I and our families and our circle of friends, they can see how other people live on TV or maybe when they go to a friend's house, but their circle of what is out there and what's available and what they are able to become is very limited. Now, when you open those doors and you start traveling the world, now all of a sudden they're exposed to when we were in Japan, hey, we took scuba lessons. Maybe when I grew up, I want to be a scuba instructor. Or maybe I want to be a tour guide in Berlin. Or wow, we met a physicist on a train once and he told us all about his lifestyle.

Jessica: So we've opened up a whole other world for them to kind of identify with and realize that there's many different ways to live a life. And maybe when they grow up, they'll go and live a stationary life someplace. Maybe they'll live in a rural mountain and live off the land, but we wanted to make sure they had these exposures to different types of life and not kind of be indoctrined in is the way you do life. You do this, you go to school for this many years, you buy this house, you buy this dog, you buy this car, and this is what everyone does. Anyone who's been traveling will tell you it's the best thing that ever happened to them. And I really think that it's been great for Will and I as a couple and individually, but it's been mind blowing for the children. And I cannot stress enough how mind blowing it is.

Jessica: There are days that are really hard on all levels for Will and I as adults from financial to emotions, to the logistics, but we look at the kids and we look at how much they've grown, how intense and powerful their relationship is with each other, they are best friends, how they see the world, how they approach the world from a humanitarians perspective, and how they truly love traveling. And everything else that goes wrong from day to day is just, you just forget about it. It really has been the best thing we have ever done for their life. And there's some other things that we think, well, nursing was a really great thing. We don't let them watch TV. They watch movies and stuff, but not TV. Wow, that was really great. But traveling, that was whole other level great. And I wouldn't change it for the world.

Will: And the fascinating part is that this is now their normal. So they don't look at this like it's a [page 00:16:12]. They look at this as if just another day in their routine, which is life. And when things go wrong, because things go wrong, they don't start to say, "Well, I'm ready to go back home." It's like, okay, how are we going to deal with this? Because they know no other at this point.

Kim: I know my question wasn't very articulate, but you both answered exactly what I was hoping that you would say. And I think it's fabulous and a really strong message to people listening who say, "Oh, we can't do it because the kids are settled" or "We'll do it when the kids are older." There's no good time. Just if you want to do it, do it. Are we on the same page?

Jessica: And it's really fun. We're not in our thirties anymore, we're 39 and a half. No, I'm just kidding. And we don't have the same energy level. And as we age, we look at things differently. And there are times where I think I have this cool open mind. And then the kid says something and something happens and I go, wow, I'm slugging along here. Let's pick this up. Let's have some fun, let's look at things differently. So it's a whole different way of traveling when you're traveling with these young, energetic teenagers who see the world so differently than people when we're starting the aging process. I mean, we're not like 110 here, but we do, our views and mindset and everything changes. And it keeps us fresh and young and open-minded and experimental, which is really great. Like we're always trying new things because they're the catalyst and saying, "Well, we can do this. Let's do this." And Will and are like, okay, let's do it.

Kim: And I like the fact you're referring to your age without saying we're in our forties, because come on, that's exactly... you're in your forties. Let's face it. What I want to hope to achieve by the end of 2020 is to get out of this idea, people, that there are young backpackers and then there are moms and dads and then there are gray nomads. There's no demographic to travel. For me, it's a mindset. So just because I might be a few years older than you, not a lot, by the way, and I'm in a van, doesn't make me a gray nomad. To me, that's telling me that I'm old and on the way out or something. No, I'm adventurous.

Will: I'm a recent graduate to the 50 year old club.

Kim: Yes!

Will: I just heard.

Jessica: That's true confessions by Will.

Kim: I love it. I've got to... Yeah, same. That's-

Will: Besides my parents, you're the first person I've ever told.

Kim: I feel so honored, I really do feel so honored. So I love what you guys are doing. I love the fact that you're traveling as a family. You call yourself World Towning and you say that's a philosophy.

Jessica: Yep.

Kim: So tell me a little bit about that philosophy and then how it became your business?

Jessica: So World Towning, we started our World Towning business several years ago. And the main goal with the business was to provide resources, consultation, coaching, whatever you want to call it, to people who thought travel was only for the rich and impossible for them to do. So what we've done is we've walked people through all the logistics to get to full-time travel. The insurance, the wifi, the medical, the visa. If they're traveling with children, how do they navigate that? Local schools, do they want to unschool, local school, language schools? We started the business because that year that we planned for our full-time adventure was horrifying because we were trying to live in one world and plan for another. So we were working like crazy all day and kids activities and social commitments and work stuff. And then at nine o'clock at night, we'd sit down and try and figure out all these logistics.

Jessica: And there were so many times where we wanted to say, okay, let's just forget about this. This is ridiculous. What do we think we're doing? Who do we think we are? Because at nine o'clock at night, you're tired. So our plan has always been to help people work their way through the logistics of doing this, presenting them with the good, the bad and the ugly so they can understand what they're getting into. We don't candy coat it at all. And help them through the logistics so they're able to realize this is possible and get out here traveling. And we've done this for three and a half years now with people anywhere from age... our youngest has been 32 and our oldest client has been 70. And we offer private consultations as well as a university 10 week session.

Jessica: And it has been incredibly incredibly... Obviously it's a business, we get an income from it. But from a personal level, it has been so incredibly inspiring to see people of all age, all income, all different cultures really take this and say, "I'm going to do this" and then watch them launch. We have clients out all over the world. Right now, even during COVID, we have people that have hunkered down in various countries across the globe and are still doing this, are determined to do this. And World Towning, if we're going to put a tagline on it, is just adventuring and traveling through the world one hometown at a time. So finding your little places along the world and making that your new normal and your new home.

Jessica: It's been incredibly rewarding. Obviously during COVID times, it's been also incredibly challenging because no one is traveling now and no one is thinking about learning the logistics of traveling right now because they're just trying to survive. And so another kind of part of our business is a year and a half ago, we launched group trips and we had our fabulous first group trip where we took 16 people with us to Morocco for 12 days. And we traveled all around Morocco, more off the beaten path and more with local experiences than your typical tour. And we had several trips for 2020 which we had to cancel because of COVID, which has been really hard and heartbreaking.

Jessica: But like we were talking about before, Kim, before we started taping, that you had mentioned a quote about someone who was saying, "We got to find the good things we can take out of 2020." And for us, it's kind of revamping the trips and launching with more once 2020 is open because we do believe people kind of from 2020, it's been a real eye-opener about life and seizing the moment and going after those big dreams. And at any point, we're realizing how fragile this is and it can be taken away. So let's kind of make those dreams happen, learn something new during COVID and come out and travel, or if you want to start a daycare, if you want to go backpacking or whatever your dream is, a farm, kind of make all that happen in 2020.

Kim: But really we're born, we die, and it's what we do in between that matters. Doesn't it? So what would you find final message be?

Jessica: It's so true.

Kim: Yeah. Will, then Jessica, as we wrap up, your final message to people listening?

Jessica: Well I'm going to go back to what you said earlier, Kim, about the age of traveling. I think that's really, really important. If someone's listening to this and they're like 32 and they're like, "Well, I'm going to do this when I retire, but I really want to do it now" or someone's 65 and saying, "Well, I don't know, am I too old?" My message is it's never too late. It's never too early. If it's right for you right now, make it happen. And age should never ever be a deterrent from you doing something you're really passionate about.

Jessica: And I think one of our biggest fears, Will and I, we don't have too many, but one of them is regret. And you don't want to get at that point in your life where you're 85 and you're laying in the bed and saying, "Gosh, I should've went at 65, but everyone was telling me I was too old." And it doesn't have to be travel. It can be whatever your dream is. So I guess my one big takeaway is it's never too late and it's never too early. If it works for you and it's something you're passionate about, don't wait.

Will: I'd rather be working at a very sort of entry level job when I'm 80 and knowing that I've lived my life when sort of I had the means and the capability to experience the things that I want to. Because I know my energy level is not going to be the same sort of forever. So we're taking advantage now while we can, while things are sort of spectacular in our eyes.

Jessica: And I think I just want to add one little thing because we are in COVID times right now. Learn something new right now. Right? Go after that thing that you've been... Whether it's, Will referenced the ukulele, you want to learn how to play the ukulele. We have a friend that's learning artificial intelligence right now. We have another friend that's learning about horticulture. Learn something new, and then when those doors... because I know it's a really tough time for everyone right now and people are getting depressed and sad and feel like this is never going to end. When those doors open, be ready to come out blazing, right? Live that authentic life and go after whatever it is that you want.

Kim: Well said. Love you guys, love what you're doing as I said. And the site, people will just be able to get their teeth into and look at the profiles of your children as well as yourselves and be really excited. So thank you so much for sharing your story with me.

Jessica: Thank you so much for having us Kim. And I love that you're van lifeing around Australia. That is so, so, so, so very cool.

Kim: yeah thanks Jessica I think it’s pretty cool, next move for us is Victoria’s high country and then across to Tasmania which is my home state – so I am very excited for that.

Just remember as you start traveling again before you buy a travel insurance policy, check your government travel warnings and health advice – there may be no travel insurance cover for locations with a government travel ban or health advice against travel.

Next week, Lonely Planet’s latest travel campaign bye.



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1 Comment

  • Maggie Baumann said

    I am newly single and want to spend the next ten years seeing the places on my bucket list, before I’m too old or too sick to do it.

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