From Tot to Teen: How Travel With Kids Changes Through the Stages

Travel with kids changes as you go - from gear and sleep schedules to school calendars and hotel choices. Listen up to find out what 15 years has taught us.

From baby's first lap infant flight to a teen texting friends from Portuguese hilltops, family travel looks completely different at every stage. Melissa gets personal in this one, sharing real stories from nearly 15 years on the road with her two kids, why she hates beach trips with babies, a two-year full-time travel adventure, the trip that turned into a COVID quarantine nightmare, and what it's actually like to travel with tweens and teens today.

Whether you're just getting started with a baby or trying to hold onto the family travel years before your kid heads to high school, this episode will meet you where you are.

In this episode:

• Why condo resorts and vacation rentals are perfect for babies and toddlers (and when to switch to hotels)
• The stroller and gear setup that worked for traveling with two young kids
• How the full-time travel years shaped the way the family travels today
• Why you should use your school schedule flexibility window while you have it
• How to build trips around your tween's actual interests — food tours, local sports, craft workshops
• What shifts when you're traveling with a teenager

Timestamps:
00:00 Welcome
01:31 Travel with a baby
06:58 Travel with a toddler
08:21 Travel with school age kids
14:01 Travel with tweens
17:45 Travel with teens
20:33 Wrapping up

How to travel with car seats
Expert tips for flying with a baby
Useful travel gifts for families

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

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Transcript

0:02

Hey there and welcome back to Family Travel Unpacked. I'm your host, Melissa, and in case you're new here, you can find tons of detailed destination guides, travel tips, hacks, and more on my website, thefamilyvoyage.com. And if you've been enjoying the show, be sure to hit follow wherever you're listening so you never miss an episode and drop a five star review'cause it really helps other families find the show. The last few episodes have been really nuts and bolts advice for travel with kids. So this week I wanted to switch it up and get a little more reflective, maybe even sentimental. We've now been traveling with kids for close to 15 years, and so much has changed in that time, both in terms of the travel experience itself and also in terms of us as travelers. My husband and I barely left our home states growing up. So as adults we've been kind of making up for lost time, and we're taking our two very lucky kids along for the ride. By the time our son Jacob was three, he'd Lounged on the beaches of Hawaii and Puerto Rico, taken three trips to Europe and been to a handful of states in national parks within the us. And we didn't slow down when our daughter Shoshana was born either. Today I wanna walk through what travel has actually looked like at each stage: baby, toddler, preschooler, elementary, tween, and now teen. Not the idealized version, but the real version. The suntent sweats and the Croatian sidewalk protests, and the COVID quarantine domino effect- all the highs and lows because I think there's something really useful in hearing just how much things change and also how much it all stays the same. So let's go back to the very beginning. Jacob's first flight wasn't some short domestic hop to see Grandma and ease us in, it was all the way to Hawaii. We were a little nervous and we definitely massively overpacked to compensate, but honestly, I was just desperate for a getaway. I was at the tail end of an exhausting maternity leave before I went back to my really high pressure job, and I needed to decompress for a little while. Self-care before hashtags were even a thing. What made that trip work was staying at a condo resort. Having a separate living room where we could put the crib meant we weren't just sitting in the dark at seven o'clock waiting for our baby to fall asleep. We had a Ianai where Ronnie and I could sit outside and hang, a full kitchen to clean bottle and pump parts, a washer dryer for-and any parent of a baby knows exactly what I'm about to say- those inevitable blowouts. A condo resort is one of the best setups for traveling with a baby, and I'd recommend it to anyone in that stage or honestly any stage. That trip set the tone for how we'd travel for years. We almost always stayed in condos or vacation rentals. The space was the main thing, especially when the kids were going to bed early and we wanted to have an actual evening ahead of us. Back then, before Airbnb fees got completely out of control, it was usually the more affordable option too. So it was kind of a no brainer for a long time. Now on that trip, Jacob was a lap infant because we didn't know yet that babies should really have their own seat and should ride in their car seat. In case you haven't heard me mention this before, I'm actually a car seat technician in addition to being a travel blogger. So I have tons of info about travel with car seats down in the show notes. We learned more after that trip and bought tickets for the kids on all of our subsequent trips. So there was a lot of crying, a lot of walking the aisles, a lot of passing him back and forth. Honestly, he was never a great crib napper. He only really settled in a stroller or a moving car, so we weren't totally surprised. But thankfully since we were living in LA at the time, both of those flights were daytime and they weren't super long. So at least the other passengers weren't trying to sleep through a crying baby. But here's a hard lesson we learned that a lot of new parents might not realize: you can't put sunscreen on a newborn. So we rented a little pop-up sun tent and a bouncy seat from a local baby gear company. Jacob had really bad reflux, so laying flat in the sand wasn't gonna work for him. Ronnie and I took turns sitting inside that tent with him, and I'm telling you it was absolutely sweltering in there. Between that and the fact that we were basically moving an entire nursery every time we wanted to go to the beach, I mean we brought an actual bouncy seat out to the sand. That was pretty much the end of beach vacations for us until our kid was old enough to actually enjoy it and not need so much gear. I know a lot of families love beach and resort getaways with their babies, but really, I just can't understand why. After that vacation, we shifted gears and figured out pretty quickly that city trips and outdoorsy getaways worked way better for our family than beach trips, at least at that age. We went to Spain just after Jacob turned one, and that was a much better fit for us. He could ride around in the stroller or carrier and see the world around him. Then after lunch, he'd conk out in the stroller while we checked out a museum or just had a nice long walk. Sometimes we even snuck in some gelato without him knowing. And then at night, there were plenty of times he slept through dinner because it was the timing for his afternoon nap back in LA. That's not to say he slept through the night, that'd be asking too much, but we found our rhythm and definitely liked that version of travel way better than trying to get him to fall asleep in a blazing hot tent on the beach. If you're listening out there while you're walking your sleeping baby in the stroller, know that you can do it on the sidewalks of Paris just as easily as in your hometown. Now Shoshana was different. She was always a really peaceful baby and by the time she came along we had a lot more experience under our belts. We basically just strapped her in a carrier and kept going. Still no beach though. We wrapped up that maternity leave toting two sleepy kids around Europe. The contrast between those two early experiences could not have been more different. I wanna touch on the travel gear piece for a minute. Because I think it stresses a lot of families out. We were always a stroller family and we really loved the baby Jogger brand because of the super quick flat fold. It's perfect when you're hopping on and off of trains or squeezing into tiny restaurants. With Jacob we had the original baby jogger sitting mini, which was great. It's pretty light and it's compact, but it's also sturdy enough to handle cobblestones. We always brought a carrier too for places that weren't stroller friendly, like palaces. When Shoshana was born, we switched to a larger baby jogger single stroller with a reversible seat. It was called the Versa, which is long discontinued, but it's really similar to the upper baby cruz. Most of the time we had one kid in the stroller and one in the carrier. But in a pinch, we could adjust the footrest and let Jacob sit on it while Shoshana rode in the seat. This is totally an off-label use, so your mileage may vary, but it worked for us when we needed it. One of my favorite photos from that era is from a train station in Germany. We were about to head to Amsterdam. Ronnie and I each had a kid strapped onto our fronts in a carrier, backpacks on our backs and next to us was that stroller loaded up with a car seat and diaper bag in the basket, and another car seat and backpack resting in the main seat. We were quite the site, so I'm really glad that someone snapped a picture for us to remember it by. These days, there are ultralight strollers that didn't exist when my kids were tiny, and if I had a baby now, I'd probably look hard at something like the Ergo Baby MetroPlus or the Nuna Travel. Both of those fold really small, but they still allow full recline for naps. They'd be perfect for certain kinds of trips, but there's also something to be said for having a tank of a stroller when your kids are tiny, because it doubles as a cart for all your stuff. If a stroller can't also be used as a trolley, it just becomes one more thing that you have to carry or push while you're also managing everything else. Moving on, I know that the toddler years strike fear into the hearts of a lot of parents when it comes to travel. And to be honest, we were really fortunate. At that stage. Jacob and Shoshana were both pretty easygoing kids, plus they've always been each other's travel buddies, even when they were really young. Other than the occasional squabble over who got to ride in the stroller, they got along great and were mostly fun to be around. We did have the typical hangry, hot, overstimulated meltdowns every now and then, but honestly not any more than you'd expect at home. I have this great photo of Shoshana fully lying down in protest on some historic steps in Split, Croatia because she was just too hot and we weren't quite ready for ice cream yet. But that's toddler travel in a nutshell right? That trip actually taught us a really valuable lesson about snacks. When a kid says they need food, high sugar, zero filling options like juice are a recipe for disaster, at least for our family. They spike your kids' blood sugar and then bring on a crash really fast. More prepared parents are probably better at this than I am, but we learned quickly that juice in a moment of desperation was not the right answer for us. Ice cream on the other hand, much better choice to tide over an empty belly and smooth out tough moments. Like I could probably publish an entire coffee table book of my kids eating ice cream in different countries. I also think one of the reasons our kids were such easy travelers is that they just didn't know any different routine. Travel was normal life for them. They basically expected it. It was just what we did. Now the preschool stage is where our story takes a pretty significant detour from most families. I talk more about this in episode one, but when Jacob was finishing preschool and Shoshana was newly three, we packed everything we owned and left LA to travel full-time. If you wanna hear more of the details of that adventure, definitely go back and listen to that introductory episode because it explains a lot. In total, we traveled for nearly two years. The first year was overseas and the second year was within the us. But in that time, we only visited something like a dozen countries. Obviously, we traveled around within those countries, but overall we went really slowly and I think that's a perfect fit for that preschool and early elementary set. The kids were incredible. We threw a lot at them. Six hour drives, hikes in the desert, two hour history tours in big cities. The key for us was always making things approachable for them and building in balance. We were getting them ice cream after every hike in the desert or hot chocolate after hikes In Patagonia, an art museum would be followed by playground time. And some days were entirely theirs, like visiting a children's science center and then getting pizza in Rome instead of visiting yet another beautiful church. But here's the thing I wanna say to anyone in that preschool or early elementary stage: don't feel like you have to cram everything in. Part of what made that year so magical was that we could go slow. It was our life, not a break from our life. When you're not racing through a two week itinerary, everyone, the kids and the adults, is just happier. Of course there were really hard moments. There were meltdowns from both kids and adults. Sometimes there were people we encountered who made our kids genuinely uncomfortable. There were a couple of hospital visits. And there were entire countries we scrapped from our plans when we felt like they were blowing our budget. I remember one long drive in New Zealand when the kids just wouldn't stop bickering to the point where it was a safety distraction, but we had to cover a lot of ground before it got dark. It probably wasn't our finest moment, but Ronnie pulled the car over and we just yelled at them for a solid five minutes. We aren't big yellers, so I think they were honestly too stunned to even talk for the rest of the drive. Again, not our best parenting, but that kind of stuff can happen no matter where you are in the world. There were also plenty of airports when the kids were just being kids, but we got really frustrated with them. You know, no one likes waiting in line for an hour at immigration, but as adults we understand that you just kinda have to suck it up and be cool. Obviously, kids are gonna be bouncing off the walls at that point. You know the challenges of this age group, they don't care what country you're in or what kind of fun activities you have planned. Kids are just gonna be kids. But overall, it was incredible. We watch our kids become more confident, more adaptable, and more curious. We saw them make friends despite language barriers. They didn't have some of those social inhibitions that develop later when they get self-conscious. And maybe most importantly, they became each other's everything. I really think that year is still the root of how close they are, almost a decade later. now, one wild card we hadn't planned on when we were raising these young travelers was a global pandemic. You know, obviously there are plenty of things that we'd all like to forget from that time period. Like masks and exposure, timelines and tests to get on planes. The whole situation definitely shaped our experience of traveling with elementary schoolers. By the time we could really travel again, Jacob was going into fourth grade and Shoshana was finishing second grade. So our first major trip after the pandemic was to Alaska in August of 2021. And here's where things get a little chaotic. Because of those pandemic uncertainties, the school calendar wasn't finalized when we booked our trip. So the kids ended up missing the first four or five days of school that year. Fine, a little disruptive, but manageable at that age. Then just a few days after we got back, Jacob tested positive for COVID. At the time, our school's policy was a 10 day quarantine from the date of a positive test, or from exposure like a sibling. So both kids were at home. And then a full week later Shoshana finally tested positive, but that reset her clock for another 10 days. So that Alaska trip ended up costing us a lot more school time than we ever intended. After that, unfortunately we felt like we had to get pretty intentional about the school schedules. During elementary school we tried to have the kids miss at most two days for any given trip. And I wanna say something here to parents of younger kids who are stressing about this. When your kids are in preschool or early elementary, you have so much more flexibility than you realize. We used to do most of our trips in April, may, September, or October- shoulder season gives you lower prices, fewer crowds, and it just didn't matter if they missed a few school days at that age. Use that window while you've got it'cause it goes fast. The other thing that defined those elementary years was that we had a ton of post pandemic pent up travel energy, let's say. So we went big Hawaii twice, Mexico twice, Costa Rica, Iceland, Alaska, Italy, Japan... bucket list kind of stuff. But something interesting shifted in that period too. Between school, activities and Ronnie's job. Everyone got busier and that meant everyone started appreciating trips that included some real downtime. We went to Costa Rica for spring break last year, and the kids loved all the adventurous activities, but they were also really happy to just sit by the pool at the resort for a couple of days. And when we plan weekend getaways now, sometimes the kids specifically request somewhere like let's say Hyatt Regency Lost Pines or Coconut Point where they can just let loose in the pool and not leave the property other than dinner. They don't wanna go out and do tours and activities. I still make sure our overall travel plans for the year have a good balance, but I've learned to lean into the relaxation trips more than I used to. It's not for me- I could still go, go, go, but the rest of the family really needs it. I talk a lot about how we balance different types of trips in episode three, how to choose your next Family travel destination, if you wanna go deeper on that. We're now living through the tween years with Shoshana. Something really cool happens around this age. The kids start developing their own interests, and if you're paying attention, travel becomes a way to feed those interests in ways that'll stick with them for a long time. Think about what your kid is into. Have a foodie? Build in a cooking class for a food tour. We did a cooking class in Japan a few years ago, and it was honestly one of the highlights of the trip for all of us. Sports kid? Catch a local game. We went to a baseball game in Tokyo and a soccer match in Porto, and the atmospheres at both were just incredible. For an artsy kid. Find a craft workshop like the glass and mask making workshops we did in Venice, or the tile painting we did in Portugal. When you connect, travel to what a kid already cares about, you stop dragging them along and they start showing up, with a better attitude, no less. And at this age if you've been traveling all along, your kids might start coming to you with ideas. They'll go online, find something they wanna do and just show you. I love that. It tells me that my kids are starting to see themselves as travelers, not just passengers. Here's a great example. When we were planning our Italy trip, Jacob was studying ancient Rome in school and he told me he really wanted to see the coliseum again now that he was older. It wasn't gonna fit into the main itinerary we had already mapped out, but I was able to make it work for the two of us to go a few days early and explore Rome together. It was such a special and unexpected gift. He still talks about those days and he's really excited to go on another adventure with me. Both kids are interested in more of that one-on-one travel now, although they still mostly wanna travel altogether as a family. Here's the thing I wanna say about tweens though, because I think it gets overlooked. Despite all this growing independence and developing opinions, kids this age still really wanna be with you. They still look to their parents as leaders of the trip and everything else. They're not teenagers yet trying to prove they don't need you. They're somewhere in between and I think that's actually a really sweet spot. They're old enough to be great company and young enough that a trip together still feels like the best thing going. Something else that shifted for us at this stage is where we stay. For most of the kids' early years, we defaulted to vacation rentals and condos, and that made a lot of sense. The space, the separate bedrooms, the kitchen. But somewhere along the way that math changed. Our travel time's a lot more limited now and honestly, the last thing I wanna do in vacation is take out the trash and strip the linens. We've also gotten a lot better at booking hotels on points, primarily through Hyatt because they offer great value, so a lot of times hotels are actually less expensive for us out of pocket than a vacation rental would be. And just to be real for a minute, now that I'm a mid forties mom of two kids, there are plenty of nights on vacation when I fall asleep before my kids and they tuck me in, even if we're all in one hotel room and the lights are on while my husband and son stay up late watching a movie. But my kids, they love a great hotel at this age. When they were tiny, they didn't care where they slept, as long as there was a crib and a pack of wipes nearby. They were also too small for a lot of the fun activities and amenities that some of these nicer hotels offer. Now that they're older, they can really appreciate it and make the most of some of these places. Plus they're old enough that I can relax and let them roam around a little while I enjoy a good book and a fruity drink. So I'd say these days we're probably about 70% hotels and 30% vacation rentals, depending on the trip. Obviously, there are some places where an apartment in the middle of the city makes more sense, especially in places where the room occupancy tops out at two people. Because plenty of tweens are still young enough that they might not wanna be down the hall in a separate room in the middle of the night, and you gotta embrace that sweetness. We stay at a lot of Hyatts and we've gotten pretty good at maneuvering our way into suites, which kind of gives us the best of both worlds. We get some separation and a little more space without the vacation rental hassle. And for the kids, there's something about a really nice hotel that just makes it feel more like a vacation in a way that an Airbnb doesn't. At this age, sometimes the right property is the destination. And that brings us to today. Every kid is different, and I wanna acknowledge that upfront. I know I'm still lucky that my teen actually wants to travel with us, but what's shifted in these teen years isn't so much whether or not my son wants to come along, it's that the dynamic starts to feel more like traveling with just another person rather than traveling with my kid. On our Portugal trip this spring break, Jacob and his friends were texting each other photos from wherever they each happened to be, and they were talking about the pros and cons of different destinations, travel's becoming something he wants to share with his peers, something he's proud of, not something he just goes along with. And that's a pretty cool thing to watch. However, the school schedule piece has gotten so much harder. I'm not gonna sugarcoat it. We try not to miss more than a day of school for any trip now, and sometimes there are commitments like band, theater, soccer, that limit when we can travel, even when school isn't in session. And if your kid does a travel sport or any sort of high level activity, good luck to you. Okay. Jacob starts high school in the fall, and his activities are already shaping our planning in ways that they never used to. It's a huge shift from the preschool years when we could take off any week we wanted. I won't pretend. It doesn't make me a little sad because we know our remaining years of traveling together like this are much more finite than they used to feel. And I see it in my teen, he's even feeling kind of sad about it too. But the flip side is that these almost adults make great travel companions. Both of my kids have started flying as unaccompanied minors on occasion, and they can't wait to fly solo without a chaperone. I try to have them navigate us through airports or around smaller cities like Porto or Bologna. Partly to prepare them for that independence, and partly because I just think it's a great skill to have and they love it. They feel so proud when they can make it from a museum back to our hotel on their own, especially when they know that I'm following their lead. And by this stage, the gear situation from those early years feels like a distant memory. The kids will sometimes pack their own bags, and they're responsible for their own stuff. We just walk right off the plane and go straight to the exit. Simple. Although I'll say that even well traveled kids are still kids: within the last year, one of mine forgot socks on a trip and the other forgot underwear on a different trip. So I have to still do a quick gut check with them before we head out the door, but that's a far cry from wrestling a stroller and four overstuffed bags through the airport. These days, I feel like the biggest hurdle is making sure everybody's got the right charging cables. At this age, they're capable of so much more than we give them credit for and travel's one of the best places to let them prove it. These are real people with real curiosity about the world, and in just a few short years, they're gonna take the reins of their own lives and their own travels. Getting to travel alongside them now feels completely different from pushing a stroller through a train station in Germany with a car seat in the basket. And honestly, they're both great, just in very different ways. Before I wrap up, I wanna speak directly to the parents at each stage for just a second. If you're in the baby or toddler years. Just do it. Go. You will overpack and it will be sweaty and somebody's gonna have a meltdown, probably you, but it's absolutely worth it. Lean into condo resorts and vacation rentals, get a good carrier and lower your expectations about what a perfect day looks like. It could be sitting at a cafe in Paris with a quiet coffee and a great view while your baby naps. The bar is just everyone surviving and having a few good moments. I promise, that counts. If you're in the preschool years, this is a magical window. Your kids are old enough to experience things and young enough that school schedules aren't hemming you in yet. Go in the shoulder seasons, go slow and remember that for every hour at a museum, you owe an hour at the playground, and for every hike you owe an ice cream. So pay up with a smile and just remember that these years are short. If you've got an elementary schooler, start being intentional about the school calendar now because it only gets more complicated. And don't underestimate how much your kids are ready for at this stage. They can handle a lot more than you think. Book that bucket list trip to really get your kids excited for a life of adventure. And if you're hanging out with me in the tween and teen years, bring your kids into the planning. Let them have opinions, say yes to the detour that one of them really wants. Even if it messes up your itinerary, those are the trips they'll remember. And zooming out from all of it, nearly 15 years of traveling with these kids. What I keep coming back to is this travel has given our family something that I don't think we could have built any other way. Closeness, adaptability, shared experiences that we still talk about all the time. The kids still fight over who gets the middle seat on the plane. But just a few weeks ago, they grabbed a random piece of paper and they each wrote their travel bucket lists on one side of it. To me, that's a huge win. Ronnie and I started out barely leaving our home states, and now we've got two kids who navigate foreign airports and send their friends photos from Portuguese hilltops. I know this sounds sappy, but to me it's amazing. School schedules are tighter now, and the remaining years of all four of us traveling together like this are a lot shorter than I'd like, but it just makes me more determined to make'em count. So whatever stage you're in right now, just go, as they say, take the trip. Don't wait for the perfect time, because there probably isn't one. There's just the time you have. Thanks so much for listening today. If this episode resonated with you, I'd love it if you'd share it with a family who's just getting started on their travel journey, or one who's in the thick of it and needs a little encouragement. Be sure to follow wherever you're listening and drop a five star review. As always, you can find show notes down below and more inspiration at thefamilyvoyage.com. Until next time, safe travels.