I Get It From My Mom: Authentic Conversations Between a Mother and Her Daughters on Parenting and Growing Up

Family Vacations: Traveling with Children - The Chaos & Connections

• Elissa, Ava & Maggie Klein • Season 1 • Episode 7

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🎙 Episode 7: Family Vacations: Traveling with Children - The Chaos & Connections

What do vacations look like when you add strollers, snack bags, teen moods, and group chat chaos? In this episode of I Get It From My Mom, Elissa, Ava, and Maggie unpack what it really means to “get away” as a family: from the early days of packing baby wipes in every bag to navigating teen schedules, solo travel, and why sometimes a staycation hits just right.

They explore:

✅ Why traveling with kids at every age has its own (messy) magic
✅ The real differences between relaxing, running around, and roughing it
✅ How family trips shift from survival to connection
✅ Lessons learned from big family vacations, school trips, and solo adventures
✅ And why sometimes, the mishaps are what make the best memories

This episode is full of travel stories, honest parenting reflection, and a few packing tips you didn’t know you needed. Whether you're dreaming of a tropical beach or just planning how to keep your teen happy on spring break, this one’s for you.

🎧 Tune in now and ask yourself: are you more “daily itinerary” or “go with the flow”?

💬 Follow us @i.get.it.from.mymom and let us know your dream trip—or your funniest travel fail.

✈️ Because no matter where you go, someone probably got it from their mom.


Welcome to, I Get it from my mom, where we talk about the things parents and children should be talking about anyway, but with more honesty and laughter. I'm Elissa, a working mom who loves to travel, but also knows the struggle of family trips that are anything but relaxing. I'm Ava, I'm 18 and I fully believe vacations should include two things, ocean views and no alarms. And I'm Maggie. I'm 15 and I want activities, cute outfits, and good food. Today we're diving into the highs and lows of family vacations, how they've changed from when you were babies to now what we've learned and how travel can bring families closer or make us temporarily want to run away. And you may have very happily noticed that Ava is finally healthy and back with us for this podcast. Yay. Oh, I'm glad you said happily notice. But what the audience can't see is how tan you both are. Since everyone did just go back from your first vacation without me. We totally missed you. If that helps. I mean, kinda. All right, let's go way back to before kids, before packing cubes, before asking, is that liquid under three ounces? Dad and I were your classic overworked couple who took trips to unwind. We traveled to places like Iceland, Greece, new Orleans, California, tucked away Caribbean islands with zero bedtime routines or nap windows to worry about. I feel like I keep learning about more of these trips. You two went on without us the other day. I learned that you guys went to the Olympics. I didn't even know that. How could that have even been fun without us? And I guarantee there were still naps by the way. For sure. Maggie. We are the best Nappers. And we did gloriously enjoy a life before children. If you can imagine, we'd wake up, maybe grab breakfast and not have to debate whether the day plan included a waterpark. Well, was dad always the vacation planner? Yes. It started with our honeymoon. Actually, I bore the brunt of the wedding planning. Well, really, Grammy and Papa did. But I had a lot to do with it, so I asked him to take on the honeymoon planning and he excelled at it. We had the most glorious and adventurous trip to South Africa and the Island of Mauritius. Dad arranged everything from flights to cars, to hotels, to safari game drives, to dinners on the beach, and he's been our vacation planner ever since. You guys clearly got to go to some amazing places. Yes, we were very lucky. Dad's work often took us both to incredible places. Most memorable being the Olympics in Athens, Greece, that I've alluded to towards the golf ProAm in Pebble Beach. So I got to see lots of celebrities. We went on an island adventure in Nevis, went on many trips to Charleston, and I learned how to ski on trips to Vermont. But you had work trips too, right? Yes, but those were without dad and involved a lot more work than some of his did. But I've been able to travel everywhere from London and Paris to all over China to even Russia with work. The opportunities have been amazing. Well, it's good that you and dad like the same things on vacation. Lots of relaxation with some elements of fun and adventure. Yeah, we've never been the super spontaneous types, as you both know, but we've always loved traveling, so I do absolutely recommend for anyone listening get lots of travel before the kids come, or multiple kids come, because while vacations are amazingly fun with children too, truly, but they are not the same. So book that trip, sleep in order, the fancy wine. But let's jump into, once you guys came along and you eventually did come along when your babies vacations were less vacation and more survival with the change of scenery, the amount of stuff we brought, bottles, diapers, wipes, toddler snacks, toys, backup outfits. I've always said they were more like relocations than ca banca than v vacate. I've always easy for you to say clearly. Have not always said that. I've always never been able to say they were more like relocations than vacations or stuff, and chaos still followed. Well, what kind of vacations were best when were babies? Well, we actually lead towards two things. One direct flights. And two, I hate to say it been nicer hotels. Not that you have to spend a ton of money, but hotels that have cribs and high chairs and a kids' playroom and maybe a nighttime babysitting service. You know, those things made it a lot easier and a lot more enjoyable. Our first real vacation with you, Ava, was to a Caribbean island. When you were like eight months old, you slept in a rollaway crib. In the closet. Um, dad would do the 5:30 AM shift with you taking a walk in the stroller and giving you a bottle. I'd come outside at 7:38 AM you'd both be past asleep, under an umbrella out near the pool. And then we'd spend the day splashing in the pool, dipping our toes in the beach, sand, playing with blocks in the kid, playroom with naps, diapers, bottles, baby food, all in between. Wait, wasn't that the vacation that you met Conan O'Brien because he had a baby there too? Yes. Yes. Conan had two children and he and his wife and his children and their nanny were actually vacationing there. and we befriended them. They were like our vacation friends that week. That was very cool. Daddy's cling to fame for sure. We even at pictures, right? So, but the most memorable part, Ava was being away with you. Yeah, I bet. That sounds fun. But there had to be some horror stories from traveling with us as babies though. No. Oh, we weren't perfect. No, no, definitely for sure. Definitely not perfect. Ava was terribly sick when we took her to the Dominican Republic when she was like less than two years old. Not my fault. Um, we almost had to take her to the hospital there, but thankfully met a wonderful American doctor at the hotel who helped us out. And Maggie, we learned that you get plane sick when you are about six months old on our way to Florida. Being the great mom I am. I had a spare set of clothes for you. The best mom being the great mom I am. I had a spare set of clothes for you, but a last nothing extra for me as I was covered in your puke. Ah, sounds not so fun. So why even travel with us at that age? You know, it was about making memories even for us chaotic ones, yes. But memories. I have pictures of you both in matching bathing suits, holding popsicles bigger than your faces. You enjoyed the pool in new places. You actually both traveled pretty easily. You eventually napped in a stroller on a launch lounge chair, wherever we were. And remember, we worked full time. So having a week off with just you and no outside childcare was great for all of us. Even if we were exhausted, we were together away from work and laundry and dishes. I am sure he definitely appreciated it. Even if we did ruin some meals with crying and interrupting your wine time seriously. So interruptive of the wine time. All right, but once you were in elementary school trips got easier. You could eat real food. Walk around on your own, carry your own backpack. Honestly, I think anything with a hotel pool worked for us and we loved the pools and water slides and at crayons of Atlantis in The Bahamas. Yeah, absolutely. You were curious, you were interested, you were fun and less scheduled, so fewer meltdowns. Generally. We could go to museums, walk cities, and you actually remembered things. It was nice. That's when the Disney years came along. Oh God, yes. Disney World, Disneyland, Disney Cruise. I'm done with Disney. Well, I know there's a lot of Disney people out there, but what about advice for people just going to Disney? All right. Yeah. I'll preface this with. We are not some Disney obsessed people, so we didn't have some particular anything we absolutely need to do. There were no characters you were dying to see, which helped. In fact, you were both a little skittish of characters, which is good. So you never made us wait on those like long hot lines for hugs or autographs or whatever, fine by us. And I would say rather than paying a lot of money for that whole like bi bitty bty salon thing they have or whatever we dressed you in, dress up clothes or nightgowns that we had and we put, you know, our hair in a bun and you guys were happy. You didn't need all that and we didn't need all that. So that really, really helped. And we just like anything else, we never overscheduled you a little kid. No way. Can do a full park in a day and night. So we go in the morning, come back and swim and nap and then, you know, decide do we go back in the evening? Do we do something else? We use Fast Pass where we could to avoid lines or whatever they call that these days. That definitely helps. And we knew your meltdowns weren't thankfully kind of valid. You were hungry or tired or hot, so we worked around them and accepted them. We never expect anything to go perfectly, but I will say big plug for Disney, they have the best strollers. I think they still have them. They were like big and plastic. You could put so much stuff on them. Even like a 10-year-old could fall asleep in those. They have everything. Use the Disney strollers. Well, I think the best trip, we went almost to Hawaii eight years ago. We did so much stuff there. That was definitely fun. It was New Year's, surfing lessons, hiking a volcano, exploring the Maui Coast, dancing at the low out. I do remember thinking I was gonna die at that volcano though. I wanna put it out there. I was the first one to stand up during surfing lessons. Actually, the only one I think. I was the first were surfing and maybe only one who stood up during surfing lessons and our hotels had the best pools, which kept us interesting. There were so many slides and a lazy river, and the whole thing was like its own little adventure, a rope swing. The little underwater elevator they had. Oh, that's right. Oh, I forgot about that. And plus it was over Hanukkah, so we got eight days of presence in Hawaii. Yes, that definitely helped. It always does. Yeah, that was a super memorable trip. But some of the most memorable moments were actually the ones we didn't plan. Like, I don't know if you guys remember, we pulled off on the side of the road and took this like long path down and there was like this cliff and people surfing there. Or explored some like restaurants and beaches just because we saw cars pulling over. We're like, oh, that must be great, and try that. So they were less popular, but it was actually even more fun and interesting. I really don't remember that. No, of course not. I believe it. I believe that it happened, but I also feel like we had a lot of say in things we did at that age, picking our outfit or the type of food we wanted, or we wanted to just relax at a pool versus walk through a city versus being younger and just kinda. Going along with the flow. Yeah, no, I think it's important to have, you guys have voice in things and kids have voice in things. It helps set everyone up for success. And in cities like Chicago or Philadelphia, when we visited, you know, we very much geared it towards activities that you'd wanna do, like the police touch museum or going, you know, to the pier and going all rides you know, we just knew we wanted to give you options at times too. Do you want to eat this type of food or that type of food? Should we get ice cream now or do we get, you know, cookies later? I think all of that, helps even as you're scheduling things to keep it a little loose so that kids feel like they're empowered to enjoy it the way they want to also and we can't forget the contributions daddy made for always setting us up for success. He was always researching the best restaurants, the right museums to go to, the walking tours, the educational stuff. That was also still fun. Always before making sure we had the perfect things to do that would keep us entertained. Absolutely. And you know what we geared what we could see your schedule. So we didn't try to push you into super late meals or super late bedtimes.'cause that just set us up to fail. Right. We met you at the age you're at and tried our best to work around it. Um, but those school age years are actually awesome for family travel. Kids are excited to do new things and you guys still like really like to be with us, which we appreciate. Which has definitely changed. Yeah, totally. We'll get into. But traveling with teens now is like managing a lot of agendas and tastes and desires and moods and schedules. Even logistically, you're two grown girls, you really can't share a bedroom with dad for more than one night. It becomes awkward. So we need to get hotel suites or two separate rooms, which add costs and scheduling, And I tend to like activities. I can't just sit around all day and I need to plan all my outfits for the activities so I know what to pack.'cause I'm the worst packer. And honestly, I think vacations are the only time in my life that I don't want everything planned. To me, life and school are busy enough. I am good with beach sleep. Repeat a little pool, a little gym and sun. Right. And dad and I like a mix. We don't wanna be overpacked with things in our schedule, but we also just can't sit around all day. So we try to mix our vacations up. We still try to do a beach oriented vacation each year, where the days are a little laier. We pepper with golf time or gym time and long walks. And golf carts. And golf carts. But we also love that you're old enough to do real cities and late nights. So we've chosen places like Las Vegas or New Orleans to go to as a family. And I love ski trips. I'm definitely grateful you taught us to ski when we were young, so it's a nice family activity we can all do together, even when sometimes it doesn't go perfect. Yep. Sometimes you break a foot down, so wonder who causes that. Not my fault. I broke my foot. Yes, you have both far surpassed me in ski skills, but you know, I love my apre ski snack and drink time. Nothing better than I'm clipping those boots in front of a fireplace. And I also appreciate that at this age we have the freedom to do our own things without you. So we can go for a bike ride or a different restaurant or go shopping without you, me and Ava together. We can sleep in and then meet up somewhere later if we really want to. Yeah, no, we recognize that your lives are busy too, and it's your vacation, even if we're paying for it. So we want you happy and to be able to take breaks from us or each other even if needed. So we tell you when we'd ideally, like you wake up for things, but also let you sleep in some mornings, and we know you stay up late. So we now aim for nighttime activities or shows or things to do too. I also think for certain vacation, getting things like Airbnbs or rental houses made a lot of sense. So we didn't have to eat every meal out we could cook at home. Having a kitchen, having more space and rooms, and even being able to do things like laundry. Yeah, it actually helps us pack less, even though Maggie still needs to have all those, I need. What are we doing for dinner? Is it fancy? Is it all fancy? Is it a skirt? Is it a jean? Short? Is it a dress? So many options. Yeah, we've learned that traveling with teens again isn't about the perfect trip. It's about finding a balance to be together and give you independence the same way you want. And hope you'll appreciate the time we spend together and the memories we build. We definitely do. You guys have also done some traveling though without us even. Why? Daddy and I had a life before you. You have a life without us. Ava, you did a teen tour of the West Coast a few years ago and Maggie's doing a similar one this summer. Yeah, it was. It was really fun. I gotta admit. I mean, the idea of basically being on a camp that travels around the West Coast was pretty great. Seeing new cities, new friends, barely any adults around, but you know, we also had to do our own laundry, manage spending money, which was definitely a good step towards independence. And I mean, if you count traveling a college of travel, I definitely did that alone too. Yeah. Do you remember a favorite place you went to on the trip Ave. Okay. I'm a kind of an amusement park nut, so I really liked going to the different amusement parks, doing Disney and Universal, like those kinds of things that maybe I did as a kid, but now did older. But it was definitely cool to see some places I've never seen before. I Then you did the um, Olympic Park that was in Salt Lake. That was very cool. You liked that one too. Utah. That was cool. Yeah, and we've been to some of the places like Vegas or Scottsdale, but I think I'm most looking forward to the California stuff like the San Francisco or the San Diegos. Also the new. Cities and walk around places. And we've also been on many overnight school trips. Like I went to Frost Valley with school in eighth grade, which is like a camp, and we did outdoor stuff and we, it was in the snow, so we had a big snowball fight. And then know for senior year we have an overnight trip, and camp alone is a whole trip without you guys, especially when they take us on their own little small things like the three night trip to Boston or. To an amusement park too for the whole day. It's a whole trip in itself. Without you guys, it's plenty of travel without us, it seems. Yeah, and I'm definitely looking forward to studying abroad for a semester, hopefully my junior year, honestly, I'm thinking maybe Spain or Italy, but literally anywhere in Europe. I will be fine with. I loved my semester abroad in England and the backpacking through Europe on weekends or holidays or afterwards was by far the best part. And I can't wait to visit you wherever you study, since I haven't been to something like Spain or Italy in a long time. Oh man, what a tough life you have. Having to come visit me in Europe. Yeah, what a tough life. You have me spending money for you to live there. And I mean, I know plenty of people that took a gap year after high school, before college to like live abroad or study abroad or whatever it is, which is also, you know, so cool. Yeah, no, absolutely great travel. So, you know, letting kids travel independently, I think helps them grow. It teaches adaptability and real world confidence, and I'm glad we've been able to offer these opportunities to you. Okay. Let's do some fast topic q and A on vacations. Now, do you like when we travel the four of us, or do you prefer when it's with the larger family or other family friends? Honestly, I think it's kind of a mix. Sometimes it's easier when it's just the four of us on certain vacations, fewer opinions, easier to get reservations, not having to work around everyone's schedules. But we've had some amazing big family vacations and I'm really grateful that our grandparents get to take us all away and we get to travel and it's honestly some of my best memories with the whole family and cousins and everything like that are from vacations. Yeah, I definitely like hanging out with our cousins when we get to go away, since we don't do so for such extended periods of time otherwise. But I also even like the ski weekends or family friends since it's nice to get out and be with other families and kids our own age. And I'm grateful that this past week I got to have one of my closest friends come to Florida since Ava couldn't join. And it wouldn't be the same if it was just me, you, and dad. I need someone my age to do my own things with, but not being alone. Dude, I am so cool to hang out with. What do you mean? So cool. My best friend and I get that totally. All right. Next favorite vacation we've taken. Casa, hands down every time. If you don't know what we're talking about, we go to a resort called Casa de Campo and the Dominican Republic. We've been multiple times, and I just don't think any vacation ever matches up to it. It's not just the place it's going with family. It's the best. I don't wanna copy Ava, but I think I'd also say the same. It's just at this point, we've been there so many times that going back just feels so welcoming. We know the area, we know how to get around. Again, always going with family. It's always a different adventure every time we go, but I also think any of the small trips we've taken, we mentioned Hawaii before, which is super fun. Any place where we get to explore something new or see something new or just get to learn about something is always interesting to me. I mean, we literally lived N Casa for a month. Yeah, that's true. So over covid, with all of us being remote, we took the opportunity to live in Dominican Republic for a few weeks because at least we could be outside without masks. While otherwise, in New York City we were very trapped and you know, the circumstances were terrible and we were very remote in terms of working and school in our real lives, but we also got to live at a beach in a house and do things like zip lining and driving around in golf carts and boating, and I'm super grateful we had that time again, under the worst of circumstances. Okay. Any memorable vacation mishaps? I remember when we went to Hawaii, dad thought he was so cool renting us a sports car with no top. But we couldn't fit anything in that car. We could barely fit ourselves and we couldn't fit any luggage or beach chairs. Not the best decision. And this one wasn't really a mishap, but I did lose my first tooth in Jamaica, chewing on a towel. And I ripped outta my mouth. And then Ava, in that month we were living in the Dominican Republic, burned her hand from cooking and had to go to a doctor. Yeah. That was not very fun. And Uncle Pete always loses or leaves a bag or piece of luggage behind every single time, every, every single time. It's ridiculous. No, those are good points. I think the good news is we actually haven't had too many mishaps. Normally our flights haven't been an issue. Our hotel rooms are available or cars, like dad's such a good planner that I think we've, you know, done pretty well. We don't always go away, of course, because no one can afford to and no one always has the time to. So we've spent many vacations or holidays at home. So what's your favorite staycation activity? Well, I mean, we definitely have the benefit of living in New York City, so I mean, I think my answer's always gonna be a Broadway show, but you know, being in college, I'm definitely grateful for not going away every vacation because I like to just come home and I think I like the nights where we get to stay in and play board games as a family or cook new things when we did sushi, dumplings, that kind of stuff. It's always nice to. Have a family night in and do something new and then play a game together at the end, or watch a movie or a show. We're really good at New Year's potlucks. We are very good. I love both of those answers. Okay. Dream destination. I think my dream destination would be Europe. I definitely, I think like in Italy, I think Italy is a very good mix of like a beach in a town, which is something I like. I love a good ra, relaxing on a beach, sitting down. But I need an activity. I love exploring a new city, eating good food, and I think Italy or even just like a Greece or an just anywhere Mediterranean type. Yeah, just anywhere in Europe where there's a beach, but also a nice town to explore is something that keeps me entertained and I really wanna see the most. Well, that was also my answer, but I'll answer something else. I guess kind of. I would also love like a London or Paris, that kind of thing. Definitely just, you know, a new city. And you know, I would never complain about being taken to Paris, so definitely cannot. You guys are so deprived. All right, well I actually have a long list and we're deprived. So my first is, I'd actually love to take you on an African safari. Daddy and I had done it on our honeymoon and we actually said, when we have teenagers, we'll do this again. You're teenagers. We're slowly missing the opportunity, but it's something, I think it's just a great. Totally different type of experience. That was great. I've never been to Japan and Korea, which seems so far. I wanna go to Japan too. Yeah. But they're supposed to be beautiful. We love the food. That's true. True. Um, there's so much, again, Ty, different types of cities and things to explore. So I think that would mine, I've always wanted to go something like Bali where you have one of those like. Huts over the water, whatever. Yeah. I don't think this is actually family versus like me and daddy more romantic or even a fun girls trip where you're like living in like island tiki hut type thing and. So that's always good. Um, let's see. I have others. I'm, I've never, I went to Italy when I was much younger, backpacking, so I've never been back as adult. So dad and I would love to explore that together. And I'd say lastly, Israel, I went as a teenager. None of you have been there, including dad. I don't know that we're super comfortable going now, but I certainly absolutely 100% wanna do that with the family. Definitely. And experience that together. Really what it means is we're gonna have to, you know, keep working to earn money for all these vacations you wanna take is start negotiating with work. Get many more. I got two jobs this summer. If it helps, I feel like the mean is Italy. So I go Italy. Italy first, sorry. Maybe on the way to Japan and then we circle back. We'll, for Africa, yeah, totally. Oh, in Australia, we've never been to Australia. We have too many bugs. I'm terrified of, sounds like too long of a plane ride for me. Okay. Snakes, maybe there's Australia then. Alright, so we've been really lucky, obviously, in having this conversation that we're looking back at 18 plus years of travel here. Yeah. I mean, I think we vacation well together, honestly, as a family. I mean, sure there's always little mishaps, or we get on each other's nerves every once in a while. Never get on each other's there. That happens at home. I actually think that most vacations we tend to be even more cohesive. Yeah, I agree. I agree, and I love how we've always gone to explore other countries, national parks, cities, and especially other cultures. And in some case, gone to do it with extended family too. Yeah, agreed. I think travel teaches us to show up, be present, be flexible, be with each other, and not work, which is the best part. So thanks girls for joining me on this trip down memory lane. You see what I did there? Oh, yay. Funny. So funny. And to our listeners, we hope it made you laugh, not along, and maybe even rethink your next vacation. Follow us on instagram@i.get.it.from.mymom lot of dots. And tell us what's your dream trip or your funniest travel fail. And remember whether you're roughing it in a tent or something, we would never do, never or sipping mocktails. Poolside. The best trips are the ones with stories. So like, follow, subscribe, and share this episode with someone who eats a vacation or is planning one with kids, and we'll see you next time. Hopefully somewhere warm.