Traveling with kids – our successes and failures



When I was 7 years old my parents took me and my then only 4 siblings in a 6 week road trip around the United States. At the time and for the next 25 years, I didn’t fully understand why this was a perfect choice, I just knew it was a great experience. Now that I’m a parent of only 2 kids vacationing and traveling has become something that I’ve obsessed about – working full time means I NEED a vacation to spend time (real time) with our kids, but often when done wrong that vacation feels more like work than staying home.


Since we had Charlie 2 1/2 years ago, we have travelled a lot – both for work and play. Part of me is proud of us for not letting those kids inhibit our love of travel and the other part of me wishes I had slept more. We went to Spain when Charlie was 20 months and I was 7 months pregnant with Elliot and learned a lot.  Then we spent a month away from home in December working in New York and “vacationing” in Portland  – with both kids, and learned a lot. Lastly, and quite psychotically, we decided to bring them both to Australia 2 months ago (for Brian’s work), and we learned a lot. There are some things that we’ve done right and some that I would never do again.


This is neither a how-to nor a cautionary tale. It’s our experience and is probably super specific to people with two small kids (one kid now seems like CAKE), but hopefully a relatable one. Here we go.


The successes/what we did right:


Success #1. We go. That right there is a huge accomplishment that deserves a pretty large pat on the backpack. Regardless of how tired you are while traveling, seeing another culture still expands your brain. Being in a country where you feel removed from your day to day gives you a break even if you are working (like Australia). Letting your kids know that they aren’t in control of every family activity is good for them, and experiencing something new with them (whether in another country or 2 hours away at the beach) is good for them. And keeping them flexible is always a good thing. Where you go is key: our last trip to Sydney burned us in a few ways (see #4 in failures) not because Sydney’s not amazing but almost because it is so great. Read on.


Success #2. We lower our expectations. The kids probably will meltdown on the plane, they will surely not sleep through the night once you are there, they’ll wake up at 5am and their naps will get messed up. Have ground-zero expectations and then you’ll have a better time. Be prepared for the worst then when it’s “ok” you celebrate as if you are the most pulled together family ever. Kids like routine, they need schedules – if you take them away from those things there are repercussions. This doesn’t mean that you shouldn’t go, it just means that you should have lower expectations than those of perfection. Brian and I have VERY low expectations for life these days, and I think because of that we have remained as happy and stressful as possible.




Success #3. We are plane/travel prepared. This isn’t that big of a deal but look, I’ve got to celebrate the successes, so kudos to us. You guys helped us so much on our trip to Spain for plane activities and we are over-prepared usually with the largest carry-on you can legally bring, full of games, toys, snacks, and technology. Charlie is old enough to watch an iPad ’til his eyes bleed – which is a whole other conversation, I know. Basically we only allow tv on the weekends or planes so he gets so excited to binge watch something (like his parents) that he refuses to put it down and it’s become an actual problem on the weekends. He wakes up at 6 am on Saturday mornings screaming with joy, “MAMA DADA IT’S THE WEEKEND, WANNA WATCH BUBBLE GUPPIES!!!” As you can imagine, we oblige because we are weak and he’s right, it is the weekend. So we are now considering giving him a little bit of tv each day and only a little on the weekends so that he stops obsessing about tv on the weekends. Update: we have now cut him off from Bubble Guppies because we realized his obsession with it was out of control and it put his brain into a loop. Again, it’s a longer conversation, but point being, on the plane he will watch ’til his eyes bleed and while it’s GREAT for us, it gets to be quite upsetting by hour 7. We can derail him into food, games (as long as we are active participants) and have found stickers, transformers, cars, and magnet games the best for traveling. But never have we said “shit we forgot the ….” on the plane. We are overly prepared.


Success #4. We bring familiar sleeping stuff. This might seem obvious but use the same pack ‘n play and bring any blankets, loveys, and a couple of their favorite stuffed animals to help them transition. There is no way Charlie would go to sleep well in a random room with random blankets.


travelling with toddler


Success #5. We prioritize our fun over their schedules/rules. Vacations are for us more than them (hell, every day is a vacation to them) so yes, we are selfish. If we want to go out to dinner, which makes them an hour or two late for their bed-time we are fine with it. If we want to have a conversation after dinner and don’t feel like going through the proper hour and a half bedtime routine and instead put on a movie for them, then we do that. We skip naps, sleep on the go, give iPads at restaurant tables – we avoid it, obviously, and we are ashamed, but Brian and I need to be able to have a conversation every now and again because our marriage is more important than looking like good parents in front of strangers. Hell, since I’m being honest, we’ve even given him an iPad at 6:00am in his crib so we can sleep in ’til 8am. NOTHING makes you feel like a worse parent then giving your 2 year old an iPad in his crib, but we are weak after a night “vacationing” and we frankly really need that sleep to be better parents all day. I’m not saying you should break all the rules, too, but if it helps knowing that we do then go for it.


Success #6. We generally stay in rental homes versus hotels. We love Kid and Coe (which is a family home rental site) and of course Airbnb and don’t really do hotel rooms anymore. While we were in Spain, we stayed with friends in a huge house 1/2 of the time, then in hotels because we only wanted a couple nights here and there, and Charlie just slept in our room which meant that we all had to go to bed at the same time (which is a bummer). So now, with two kids, we really can’t do hotels anymore. The amount of closets and bathrooms we’ve tried to shove his pack ‘n play into is large. Now we have to actually “plan” our trip which isn’t our forte – we are those people who have always shown up in a country and found a hotel/hostel that same day so we have to be more ahead of the game now. That eliminates resorts since we need full suites in order for our vacation to not be compromised (see #5). So houses it is.


vacationing-with-kids (1)


Success #7. We vacation with friends who have kids. Most of you know how much better this can be but for all you newbies here goes: Multiple kids kinda babysit each other and since going out at night is harder (if not impossible) to do without booking a local random sitter, then you want to at least throw a mini-party in your house. Just make sure to take some time for only your family, so you get that intimate bonding time. Currently our favorite vacations of the last two years have been going to Spain (with friends in a huge house they were staying in all summer). Renting a big cabin in Sunriver with my best friends from growing up and their kids (above). Renting a beach house in San Diego with Brian’s family, and last weekend, unexpectedly we rented a farm outside of LA (literally 20 minutes from home) with our LA best friends (and toddlers) for the weekend. They all thought I was nuts for renting a house in Encino for “vacation” as it was so close, but man, it was perfect. All we did for three straight days was lay around on blankets on the grass, gab, drink wine, explore the farm with the kids, watch the kids play (with miniature horses) and bbq. It was absolutely magical because we got to TALK and be around our kids (where that cuddly baby barely left my chest).




Anyway, friends for you and for your kids make the whole trip so much more enjoyable. Sure, its nice to go just your family but in our experience all of our friends are so busy with life that sometimes vacations are the only way to actually catch up with them.


Success #8. We give each other breaks from parenting. In Spain, Brian and I were pretty good about saying “you take the afternoon off, I’ll take Charlie” and I remember skipping around Barcelona with my best friend, shopping, having the best day of my life, toddler-free. It was so good for our marriage. I’ve got to remember to do that more often because nothing makes you love your partner more than a day (or a few hours) of guilt-free parental freedom (the key to this is guilt-free … if you feel bad during those hours then it’s basically ruined – so that is why offering the time off instead of having to ask for it is key).


Emily Henderson Traveling With A Toddler


So now, the fails or what we have done wrong:


Fail #1. We let the kids sleep with us – this has happened on virtually every trip and it’s been really hard to break. One of them starts crying and could wake the other, so we let them come into bed with us. They like that and the next night are psyched to do the same thing. It’s fine, nobody dies, but when we got home from Spain, it took 2 months for Charlie to sleep through the night again. Maybe even more. I feel like he just started sleeping through the night again a month ago. If you are weak like us, then you are probably going to do this, but I am officially warning against this or just know it’s a really hard habit for them to break.


Fail #2. We stayed in a hotel. As I said above one hotel room is not ideal. Its doable for a night or two and if you don’t mind keeping your kids up later then it’s ok, but going to bed at 8:30 on vacation isn’t my ideal scenario. In Spain I was pregnant so it was kinda ok. Brian and I marathoned ‘The Affair’ on headphone splitters off my laptop after we knew Charlie was asleep. A couple hotel rooms had large closets and we put his pack ‘n play in there, but generally trying to put everyone in one room can put a damper on your vacation (answer: rental homes or adjoining rooms but often that is super expensive).


Fail #3. This is less of a mistake and more of a ‘we still don’t know what to do but we have some advice based on our trips‘. To book a plane seat or not for a child under 2 (but over 1) is such a hard decision? UGH. We’ve done it both ways. When we went to Spain, we didn’t book a seat for Charlie (he was 19 months) and it was very, very, very stressful until we got some people to move around to give us an extra one for him. Had there not been an extra seat we would have been BUMMED to say the least. We called the airline every day to see what the chances were because if it was getting booked we were going to purchase one. I was super pregnant so Charlie would have had to of sat on Brian’s lap for 12 hours. Nobody slept either way, but at least by scrambling to find a seat we were all as comfortable as possible (which was very much not comfortable). We panicked at the airport because they said there wasn’t any room, so we tried to buy a seat day of, but then they wouldn’t let us because they said he had to be 2 years old to get a seat (on Air France, anyway) which was confusing. We ended up getting a seat for him without paying because there was an extra one. My advice is to buy if it’s under $600 (shorter flights) but not international ones. I know that seems totally opposite what you should do but international flights can be $1500 – $2k for a ONE YEAR OLD and that’s just insane. Maybe your kids will sleep on flights, but Charlie rarely did, so if you go into it knowing that it’s going to be super painful but you’ll save that money, then you’ll get through those 12 hours and live.


For shorter/cheaper flights (like to Portland or New York) we would book him a seat. We learned our lesson when he was 16 months as we went to Portland and it was the worst 3 hours of my life. He was screaming, jumping, yelling “no,” and running up and down the aisle for a solid 2 hours. Harrowing. That 1-2 year gap is the hardest because they aren’t old enough to really watch tv for extended periods of time and they want to run because they are just learning to run, which they can’t on a flight. So when its a couple hundred to add, we do it.




Fail #4 (thanks to a commenter for reminding me of this). Don’t take a red-eye unless you have to. We thought that Charlie would just pass out and we’d avoid trying to wrangle a kid on a flight for 12 hours. NOT THE CASE. They don’t sleep, you don’t sleep and then first two days of vacation at least for us were hell. For Australia we had to take a night flight and our expectations were low, thank god, because it didn’t go well as we suspected. You can use this trick though – do everything for bed – brush, sleepsack, book/bottle, etc and if they won’t go down then convince them just to take a 5 minute nap. Like no big deal, just close your eyes for a few minutes then you can watch more tv or play more, etc. They’ll fall asleep for a few hours because they’ll be so tired. But if you can opt for a daytime flight everyone is in a better mood (YOU included).


Fail #5. We don’t bring enough toys. We’ve travelled with no toys (besides plane toys) before and we’ve ended up buying a bunch of garbage wherever we are. This is why going the Kid and Coe route is good (they are family homes with toys), but it might be worth bringing a suitcase of toys if you don’t want to buy a ton for your hotel. Please note that that was one of three cart-loads of luggage above.


Fail #6. We’ve gone to big, amazing cities. We learned this the hard way and this fail is particular to our situation of baby + toddler = level of insanity that I knew not possible. The gist is this: a city offers culture, nightlife, delicious restaurants, shopping, etc – all things in which children fail at. You can’t fully experience these things with two small children who both need naps (nap trap) and if you do drag them out it’s “nice” at best. After Sydney, we analyzed what worked and what didn’t, and ultimately we realized that we went really far away to just hang out in a house in a city. Over the course of two weeks we spent enough time out and about in the city to come back with a really good experience, but had we only been there for a week, I think that it would have been a waste of a big trip with so many missed opportunities.


Our new plan is to only rent a house that is walking distance to activities – beach, lake, or a huge farm/backyard like last weekend. That way A) you don’t feel like you are missing out on culture and B) you don’t have to spend hours loading your kids in the car just to come back for a nap. We were planning the next big trip with our friends recently and they were all “Paris!” and we were all “Whitefish, Montana!” We’ve decided that until the kids are 4 and 6 (done with naps, diapers, and can maybe even get themselves dressed and fed) that we are still going to vacation, but the location is determined by what will be the most relaxing to us and fun for them, which means a nearby, walkable or bike-able body of water or nature, and a space for the kids to play. This is why people go to Hawaii. Or Legoland. Or in our case a few weeks ago, The San Fernando Valley. But look how much fun those kids had:




Fail #7. We (used to) get to the airport as if we didn’t have kids – you know, like an hour and a half early. We learned our lesson. We almost missed our flights last year, twice, because there is just so much more shit to deal with when you have kids at the airport. The stress and anxiety on the family and the kids during that hour and a half of trying to get from curb to the plane is harrowing (also if whenever possible avoid LAX, the worst place on the planet – you can get there over an hour early and they’ll say “…yea, you aren’t going to make it” because it’s so big and the lines are so long #Burbankforever). Now we get there 2 1/2 hours earlier and have such a better time.


Fail #8. We forget we have kids, and go out or stay up all night and party like we are 22 and kidless. Whatever. It’s not a mistake, and its certainly part of how we vacation, just make sure that if this is you, you are OK with phoning it in as parents the next morning. This is why god invented cartoons.


All in all I think we do a pretty good job – much like our general parenting. We don’t nail it, nor are our kids disadvantaged, and we learn so much every single day.


My general traveling (on vacation) with kids thesis is this: prioritize your sanity first, their fun second and don’t worry about anything else. Find a vacation for you where those two big goals things match up, because really when the kids are having fun we feel sane and when we feel sane, generally kids have fun.  This might mean Paris, this might mean Legoland. You do you. Meanwhile this summer we are off to Bend, Oregon, a ranch in Wyoming and Sacramento. So much for my original plan to live in Iceland for the month of August and create content from there. HA. Delusional, hormonal, post-partum Emily makes hilarious regretful decisions …


I’d love to hear a few things from you all – what is your #1 family vacation ever, where you are headed this summer that is family friendly and any lovely traveling-with-kids horror stories you feel like getting off your chest?


Liked this post? Check these out: The First Four Months With Two Kids, How I Got My Baby To Sleep Through The Night, My Favorite 8 Things About Our Australia Trip (And 1 Sad Thing).


The post Traveling with kids – our successes and failures appeared first on Emily Henderson.


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