Jessica Eastman Stewart, founder of Joyfully Managed Family and a seasoned traveler with two elementary-aged children, offers invaluable insights and practical tips for traveling with kids.

She emphasizes the importance of accepting that traveling with kids is different from traveling without them and finding ways to still enjoy the kind of travel you used to do.

From planning affordable weekend trips to world schooling, researching online, and tracking memories of your trip, Jessica shares her experiences and lessons learned to help make traveling with kids a rewarding and enjoyable experience for the whole family.

Summary

Traveling with kids can feel daunting, but it doesn't have to be. Jessica Eastman Stewart, the founder of Joyfully Managed Family and a mother of two elementary-aged children, is here to help. On a recent episode of the podcast HobbyScool, she shared her insights and tips for traveling with kids.

One of the first things Jessica emphasizes is that traveling with kids is different from traveling without them. She encourages parents to accept this mindset and find ways to still enjoy the kind of travel they used to do, whether that's by traveling solo, with a partner, or with friends who can help with the kids.

For those who want to travel with their kids, Jessica recommends starting small with a weekend trip and finding affordable accommodations with fun amenities. If you're interested in international travel, she suggests researching online and joining Facebook groups to find information and recommendations. Jessica and her family have done world schooling, which involves temporarily living in a new place and homeschooling or enrolling their kids in local schools. They found these places through Facebook groups and recommendations from friends.

Traveling with kids can be more affordable than staying at home, as summer camps can be expensive and food costs can be lower in other countries. And while there will still be challenges, like at home, there will also be magical moments, like enjoying a sunset together or learning something new.

To prepare for a trip, Jessica recommends creating a travel checklist, packing a small bag of essential medicines, and finding a way to track memories of the trip. For safety concerns, she suggests using temporary tattoos with a child's name and phone number or Apple Air tags on a necklace to locate a child in a busy area.

If you're interested in learning more about traveling with kids, Jessica can be found on her website and Instagram, where she shares daily tips for families. She also offers a free ebook with practical tips and sample checklists for travel planning.

In conclusion, traveling with kids may require a shift in mindset and some extra planning, but it can be a rewarding and enjoyable experience for the whole family. As Jessica Eastman Stewart says, "there's really no such thing as a perfect trip, but there will be beauty in whatever it is that you do, and it's worth giving it a try."

Mentioned In This Episode

• Where to find Jessica: ⁠Website⁠ and ⁠Instagram⁠

• Jessica's free gift: ⁠Little Life Hacks for Travel

• Don't forget to join our wait list for the next HobbyScool online learning summit. Our summits are free to attend and you can be the first to know when the next summit launches by ⁠getting on the wait list here.

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Transcript:

Destini Copp 0:00:00

And my special guest today is Jessica Eastman Stewart. Jessica is the founder of joyfully managed family and a mother of two elementary aged children based in northern California. She is a former classroom teacher who supports parents to create systems and routines to build in more joy and ease to the challenging work of running a home. And Jessica, I am super excited to chat with you today, especially about this topic, because we're going to be talking about tips for traveling with kids, and we have three trips planned for this summer with grants. So this is a very timely conversation for me. In particular, my kids are a little bit, I think, older than you, than yours. They're in middle school, but honestly, I think that's worse because they stay in the backseat and they fight constantly. So I'm very interested in getting all of your tips about how to make traveling with kids much easier. But before we get into all the questions I have for you, can you tell the audience a little bit more about you, how you help people, but how you really got into this?

Jessica Eastman Stewart 0:01:20

Yeah, well, it's really great to be here. Thank you for having me. I have two kiddos. They are currently seven and eight, and I help people get organized at work and at home, essentially. And I started my career as a classroom teacher. I was a nonprofit executive for many years, and I just found myself being the kind of person who lots of folks would come to me to ask for tips about how to be more productive or effective at work, but also at home. And so now I get to spend all of my time helping people with that, and it is such a joy.

Destini Copp 0:02:01

So tell me a little bit about the kinds of travel you do with your family. I know you go I believe you go, like, all over the world. So kind of set the stage for us about what you've been doing in terms of traveling with your kids.

Jessica Eastman Stewart 0:02:16

Yeah, definitely. So we don't live close to family, so our family are in the south. I grew up in Alabama. My parents now live in Mississippi, so we're traveling from California to Mississippi pretty often. Also, my husband's family is in new Jersey, so we're also traveling there. So we do regular trips to see family. That's kind of a must do for us to maintain relationships. But we also love to do we're regular day trip folks. We'd love to get in the car and drive an hour or two. We love to go. We have an annual trip with my mom's group where we go glamping every fall, and then we also love to do longer international trips. So we've done trips of four to six weeks internationally with our kids as well. So I love traveling. I got to grow up in a military family and travel around the world as a kid, and so I really want my kids to have similar experiences.

Destini Copp 0:03:11

So I definitely want to delve into that, especially traveling internationally, because that terrifies me internationally. But a lot of people probably like me, are apprehensive with traveling with their kids. What would you tell them?

Jessica Eastman Stewart 0:03:27

Yeah, I think there's a mindset that we all have to kind of accept, especially as parents, that traveling with kids is just different than traveling without kids. Before I had kids, a trip would be lots of sleeping in and relaxing and doing what I wanted to do. And that is great. And I encourage folks to figure out, especially if they have kids, is there a way you can still do that kind of travel either solo or with a partner or with friends, with kids and getting support to be able to do that. But the reality is, most of us, when we travel, we're going to do it with our kids. Sometimes I'd like to call it a trip instead of a vacation. It's a family trip because a vacation exudes all this relaxation. And it's just like weekends for me. Weekends with kids are often very fun. They are almost never relaxing to me like they used to be. And so I like to remember that when we're traveling, you're still going to have the same things that happen at home. Your kids are still going to bicker if they're little, they're still going to get up earlier than you want them to. They're still going to not want to eat that thing that you wish they would eat. All of the things that happen in regular life, that's still going to be a thing when you're traveling. The magic is in the other moments so that instead of just coming home at the end of the day and everybody kind of going to their separate spaces and maybe kids getting on screens if you're in a new place.

Jessica Eastman Stewart 0:05:09

You might have that moment, like on a beach where everybody gets to enjoy the sunset together. Or you might get to see some interesting wildlife. Or learn something new that you didn't learn before. So really, if we've got to set the expectation not that the whole day is just going to be this relaxing, beautiful thing where nothing goes wrong and imagine more, that it will have some of those unfortunate moments that are just part of regular life. And the beauty is really in all of those amazing moments in between that get to be magic instead of kind of the normal day to day life.

Destini Copp 0:05:45

And I like what you said. I call it a family trip, not a vacation, because a vacation has a different connotation surrounding it. So I love that. Now, you talked about it, you've done some international travel, or I think you also call it world schooling with your kids. So tell us a little bit more about that and what have you done there?

Jessica Eastman Stewart 0:06:06

Yeah, so world schooling would be a name that folks use to there's a lot of different ways to do it. Some families do world schooling by permanently traveling. They're like living abroad and moving regularly and essentially they're homeschooling their kids but doing it abroad and they might be going to kids programs in other countries and moving around. We like that concept, but we've learned that for us, having a home base is really important and we like routine. So I love to have our home base where we are most of the year, but I also love the ability to be in a new place for a significant chunk of the year. So that is how we like to do international travel. So we've done a couple of trips like that and we're planning more in the future. So in 2019, our kids were preschoolers and we spent a month in Wahaka, Mexico. And that is just an amazing place. It is so friendly, so family friendly and just a place where kids can really thrive. And we found a preschool that was willing to take kids for a drop in month and kind of then built our lives around that. We found a nearby airbnb. It was $25 a day. It was a beautiful home. The preschool was, I think $200 for the month, which is different than the price of the San Francisco Bay Area where I live quite a bit and we just lived there a month.

Jessica Eastman Stewart 0:07:37

At the time we had jobs that you weren't able to do permanently remotely, but we were both able to make it temporarily work remotely. So we are lucky that we have jobs like that. We're not firefighters or nurses or anything that requires to be always in a certain place. So we were able to temporarily make our jobs remote and we took some of that time as vacation as well. So we were just really unplugged. But while the kids were in preschool, we just worked. And then last summer, the summer of 2022, we spent six weeks in the Dominican Republic and there's a school there in Cabrera and our kids spent six weeks going to that school and we found some nearby housing and that was just an amazing trip. We also did a combination of working remotely and taking some vacation time and just being able to settle in and get to know folks and have neighbors and build some temporary routines but get to know a new community and figure out what's our favorite grocery store here, it was just really amazing. And also, again, just a really family friendly place. And both of those places we chose partially because they had similar time zones to us, so they were only somewhere between an hour and 3 hours different. So it wasn't too tricky to do our remote work, but really amazing trips. And honestly, if we think about the trip to the Dominican Republic, the cost of lodging plus housing plus sending our kids to a local school there was the same as staying home because it was in the middle of the summer where in our part of the world, a kids summer camp costs $400 a week. So for us with two kids, that's nearly $1,000 a week just for summer camp. And so the whole family was able to spend that time in another country for the same cost as literally staying at our house. And I think it was probably cheaper overall because lots of things were less expensive, like food costs and things like that.

Jessica Eastman Stewart 0:09:41

So it was amazing way to do that. And there's lots of places that can be international trip travel can be done like that with kids in a way that is very affordable.

Destini Copp 0:09:51

I'm just curious, how did you find these places to go, like the Dominican Republic and the one in Mexico, how did you land on them? How did you find out about them?

Jessica Eastman Stewart 0:10:05

Yeah, so the place in Mexico, we actually just asked on Facebook, has anybody ever traveled to Mexico with kids? And if so, do you have any recommendations for where to go? And it was a friend of a friend who a friend said, oh, let me ask my friend, she took her kids and then we said, oh, did you find a preschool? Did you like it? And she said yes.

Destini Copp 0:10:24

And we looked it up and it.

Jessica Eastman Stewart 0:10:25

Looked good, and we were like, okay, we'll go with that. But since then, there's some really great Facebook groups. There's one called World Schoolers. So if folks are interested, facebook groups can be a really good way to stay connected. There's programs in Egypt and Japan and many in Mexico and Costa Rica. So Facebook groups have been just searching for world schooling or world schoolers or travel with kids can be a really great way to go in and then just search for different topics you're interested in and you'll find folks. Talking about places they like to go and schools that their kids drop into and how much they cost and all sorts of things like that.

Destini Copp 0:11:07

Now, do you find it's easier to do this when your kids are younger before they get into middle school and high school, or what is your recommendation there?

Jessica Eastman Stewart 0:11:16

Yeah, well, it's certainly easy. We found it really easy to travel with our younger kids because it didn't really matter if they missed a couple of weeks of preschool. It's a little different once they get to elementary school and just pulling them out of school. Not that you can't do that, but certainly there's a different feeling about that. So now we focus most of our travel in the summertime. I had a friend who recently traveled around the world for a family gap year they called it. Their kids are high school age and the whole family just took a year off and traveled around the world. They planned that for a while, and I think they had a really positive experience. So I think it's actually a little easier with slightly older kids. I certainly have never been a parent to middle schoolers, so I'll have to get back to you in a few years on that. But I think that there's the benefit of the babies. Babies are so portable. You can just kind of carry them around and do things, and they nap a lot. The little kids need more hands on attention. This summer in Dominican Republic, our kids were old enough to just kind of head out into the yard and play with other kids, and we could just check in on them every once in a while, or some other family would be feeding them dinner and we're like, oh, great, thanks for taking care of that with them.

Jessica Eastman Stewart 0:12:34

So it was nice to they were a little bit more independent. So I really think it can be different magical at all the ages, but probably different in different ways.

Destini Copp 0:12:45

So let's just say somebody is very interested in getting started. Where would you recommend they start?

Jessica Eastman Stewart 0:12:51

Yeah, that's a great question. I think if you haven't done a lot of travel with kids, starting small is a great way to do it. Planning that weekend trip, finding the affordable airbnb or hotel to go to. If it's got a fun pool for the family, I think it's a good way to start. If you're interested in the international travel, I would definitely get some online advice and Facebook groups or just by Googling World School and see what you can find. I've got some recommendations on my blog and tips, so folks can certainly read there if they're interested in learning more. But I say just give it a try and know that it's not going to be perfect. There's really no such thing as a perfect trip, but there will be beauty in whatever it is that you do, and it's worth giving it a try.

Destini Copp 0:13:46

So, Jessica, any last minute tips for the audience?

Jessica Eastman Stewart 0:13:51

Yeah, definitely. I would say I actually have a free gift for the audience and I'll share about it where folks can find it. But essentially you'll find lots of tips in there. But here's some of my favorite ones. I think creating a travel checklist can be really valuable, and so especially if you travel a lot, your family is traveling three to five times a year, then having a checklist of, have we booked a lodging? How are we getting to the airport if we're doing that? Where are the kids going to sleep if they're little? And you might need to think about bringing a crib or renting a crib, a checklist that reminds you what to do to plan a trip, and then it reminds you what to do right before the trip, right? So you remember to turn off the heat in your house, get somebody to put out the trash or bring it back in all those steps like the planning part. And then right before we leave, what are our last steps? Make sure the cat's having a food or something like that. I encourage folks to leave things that you travel with, like in your suitcase, just permanently, right? Like if you have a laundry bag that you like to put laundry in when you're on travel, just let that live in your suitcase so that it's always there whenever you want to travel. And I even encourage folks to pack a little bag of a small amount of all the medicines you might need on your trip and just leave that in your suitcase so that on any trip you're going to have a little bit of NyQuil and a little bit of Ibuprofen and some bandaids and a little bit of antidiarhea medicine and all the things that might get you kind of over the hump if you suddenly end up feeling not so well in the middle of the night or something before you can get to a store. I also encourage folks to find a way to track memories.

Jessica Eastman Stewart 0:15:40

I think that can be it's a way to support our remembering selves, to squeeze all the goodness out of that trip by being able to review the memories as you go so that can look as simple as when we were in Dr this summer. We literally wrote memories at night at dinner. We would say, did anything fun happen that we want to remember? And we wrote it on an index card. And that set of index cards has a binder clip around it and it lives on a bookshelf. And occasionally we flip through it and remember those fun memories. It can be a little journal that you get. And each day we once went to Hawaii and I would write memories and my daughter would illustrate them when she was six. And she loved drawing pictures of the memories. I would say we saw a goat and it stopped in the middle of the road, and that was memorable that day. And so she would then draw a picture of the goat in the road. So finding a way to capture those memories along the way and planning ahead for bringing some little index cards or a little journal with you, I think can be really powerful. And then my last tip would just be to think about, if you're worried about safety, to plan ahead for that. You can get tattoos with your phone number and name on them, temporary tattoos for your kids. And so if you're worried and you want some I teach my kids that if they ever get separated from me, to find another parent, to look for somebody with kids and ask them for help and say, I need help to find my mom, here's her phone number.

Jessica Eastman Stewart 0:17:10

And they point to their arm where my phone number is, right? So you can do that kind of thing. You could get those Apple Air tags and there's little necklaces you can stick them in. And if we're ever going to be in a really busy area or, like, a big zoo where they might get separated from us somehow, we stick an Apple Air tag on a necklace on them. And so that we could pull up our phone and say, like, not just where are my headphones and my iPad, but where's my daughter? And it'll find it. So those are a couple of safety tips that can help too, if folks are worried about that.

Destini Copp 0:17:40

I love that. And I didn't even know that they did those temporary tattoos that have people's name and numbers on them.

Jessica Eastman Stewart 0:17:46

So I learned, yeah, there's a number of companies so folks can just Google, like personalized safety tattoos or something, and you'll find some companies that make them. And yeah, we love having a little bag of them for trips. And if we're going to be in an airport or somewhere else that there might be a lot of people and we might lose track of a kid. We've never actually had to use them. Nobody's ever called me because of my child's temporary tattoo, but it gives me that peace of mind, which allows us all to have a better time.

Destini Copp 0:18:16

I love that. That's some great tips. Now Jessica, can you let folks know where they can find you and talk a little bit more about your free gift also?

Jessica Eastman Stewart 0:18:24

Yeah, definitely. So you can find me@jessicaissmanstewart.com and you can find me on Instagram. I have daily tips for families at Joyfully managed Family on Instagram. And if folks want, I have a free ebook, Little Life Hacks for Travel so you can find that Jessica Eastman Stewart freebies. And in that you're going to find several more really practical tips, including the ones I just shared, as well as sample travel checklists, sample packing lists for families, those kinds of things that you can use as Google Docs and then edit them to your heart's content so that you've got a personalized one that works for your family. So I hope that is helpful for folks. I would love for as many folks to download that and use it and get more travel in as possible and.

Destini Copp 0:19:16

We will make sure that all of those links are in the show notes, Jessica, so people can just click on them and find you. And thank you so much for joining us today. I learned so much about traveling with kids, I didn't even realize that some of that was even possible. So thank you so much. You are so welcome.

Jessica Eastman Stewart 0:19:32

Thanks to everybody. I'm such a fan of this podcast, so it's been an honor to be a guest.