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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).

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7 years ago

Great article and I will be sure to use some of these tips as we have two trips coming up this summer with our 2 year old. One thing I’ve found is that our big ‘ol pack mule jogging stroller was too big for one airline and they made us check it at the check in counter meaning I had to carry my son and all of our carry on bags since I thought I would have the stroller with me. Every flight I had taken before that one we were allowed to bring it through security and check at the gate of the plane. That was the worst flight of my life trying to walk quickly through an airport in low heeled booties, carry a two year old, a diaper bag and his check on bag filled with toys. Great mention about the toys in hotel rooms or wherever you end up staying. We went to CA for my husband’s high school reunion and only brought plane toys so he was bored immediately. We went out and bought a bunch then had to find room in our luggage to get them home so as not to waste the money… Read more »

7 years ago

Great post and so much (hard) truth in it! Thanks again for sharing your experience honestly! 🙂

Lucy R
7 years ago

Thank you, thank you, thank you for this post! I love your parental honesty, the Internet needs more of this. We only have the one kiddo (who does not sit still for ONE second) and getting away to have an enjoyable and restful break seems like a task and a half (I hear you laughing at this! We are in for it with number two haha). Keep up the amazing work (parenting and design) and thanks for sharing 🙂 xx

7 years ago

Oh man. My husband is pretty eager for baby #2 and I keep thinking how hard it will be to travel with a second. We’ve taken our 9 month old to Germany and China thus far and we’ve survived and learned some lessons. These tips are great and while they affirm a second kid will make it harder, at least you’re not swearing off travel now that you have two! Thanks for the helpful post!

7 years ago

My top tips from raising two boys: camping and trips with grandparents. The former is kids’ mecca and allows for plenty of downtime for the bigs. Just being outside 24/7 makes any amount of time feel much longer (in a good way). The latter is simply genius. Built-in best babysitters ever and with double the usual adult to child ratio, everything is butter. In this instance we found renting a house together best to be on neutral turf. When visiting the grandparents it’s always more work for the grandparents since they are hosting. And usually hosting in a very pristine environment since they’ve already raised their hooligans and now want to live in peace with everything just so. Traveling by plane and carousing around Europe happened in the late high school and college years. And trust me, it is way more fun when your kids enjoy a 3-hour French lunch with wine and museums and going out on their own at night after tucking the folks in at midnight.

7 years ago
Reply to  Cynthia

This woman is a genius.

7 years ago
Reply to  Cynthia

I have friends who vacation every summer with their parents. They switch each year. One year with hers and the next with his. It’s so smart to do this if you can tolerate each other. Ha
As far as giving the kid an ipad to get some more sleep. Do it. My husband and I put a twin bed and little tv in my daughters room when she was born and once big enough we would close the door and sleep a bit longer and she would climb all over us, play and watch tv. More sleep = happier well functioning parents.

Also Emily, the fight with them being obsessed with electronics is never ending. My kids are 9 and 12 and we limit what is allowed otherwise they would look at a screen for literally 20 hours straight. There is no right or wrong answer. Just do what works best for your child/family.

7 years ago

i don’t have kids (in contemplation mode) and yet am obsessed with this post!! it may sound insane but some of these tips make sense to think about even for a couple. i love alone time (“afternoons off”) on trips, my husband just doesn’t really need that solo time, so we have to kind of navigate our needs and be genuine in our offers. or the going local holiday – sometimes we forget that we just need a change of scene and a spot just out of town is great option. or even what flights to book and what you’re willing to pay for comfort-wise. He is all about finding the cheapest route/best deal. i have flight anxiety and would pay anything to get to my destination in one shot with a reputable carrier. anyway, hopefully this doesn’t mean we will be useless at travelling if and when kids come around, but loving this round-up in any case.

7 years ago

All of this is so true! We have two girls, two and three years old, 15 months apart. Last year we decided to escape the NY cold and go to Florida for a week. We were in one hotel room and it pretty much sucked. Ha! The sun was nice, but the whole time, my husband and I were asking each other, “Are we having fun? Is this worth it?” It’s funny now, but man were we misguided when we booked that trip.

7 years ago

Our daughter (one at the time) lost it on a flight out of Las Vegas (we were connecting through there) on a Sunday. As I’m sure you can imagine our co-passengers, who had spent the weekend imbibing in Las Vegas, were treated to an extra bad headache for the beginning of the flight. That said, I found that snacks go a long long way toward in flight entertainment. You can never have enough. The other bit of advice I received before traveling with our daughter was to buy some small denomination Starbucks gift cards to give to other travelers who go out of their way to help you (or if your kid is kicking the back of their seat the whole flight.)

LA Lady
7 years ago
Reply to  Laura

Yes to kicking the back of the seat! This happens up to age 5. You spend the whole flight holding their little feet down because they CAN’T. NOT. KICK.

7 years ago
Reply to  LA Lady

Maybe if they are big enough (2?) you could walk them to the persons seat they are kicking and have them introduce themselves. Sometimes, seeing the person and hearing they could be upset if their seat keeps getting kicked will deter some kids. Or bribe. I’m not above bribing. Haha

7 years ago

Few hotels are set up for families. As you said, you want the kid to sleep so he/she doesn’t melt down the next day, but that means everybody has to go to bed at 7 or 8. Few parents are willing to put a small child in a separate hotel room down the hall. And few hotels have affordable suites or communicating rooms. Apartments are great with families. I always took little presents, mostly books and coloring books, with something to open every hour. Just opening the present was good for 30 minutes. Going home is a 24-hour schlep involving three flights, one of them transatlantic, and two sometimes long layovers. Once our kid was big enough to walk, we bought a seat, even though it was a financial strain. It just isn’t fair to the other passengers. Anyway, one year, a security person wanted to unwrap all the little presents I’d prepared. I asked why they couldn’t just go through the x-ray to show they were thin little books (wrapped separately!), but she insisted that since they were wrapped they were a threat and she had to open them. Jerk. I made her unwrap them and then re-wrap them… Read more »

7 years ago

Good for you.

7 years ago

Yes! I have done countless international flights with my two kids and this is key. If there is turbulence and the meal is delayed, there is no way to handle the epic metldowns that happen- and my children are now 11 and 7 but getting ‘hangry’ has no age limit 🙂 I also make sure to book childrens meals not because they actually like chicken nuggets (the universal kids menu) but because they will always be served first when meal service begins. My personal trick for long haul intl is to let one of the kids sleep on the floor if they really need to stretch out. I put the trays down, throw a airplane blanket over the top, and cover the floor with a few more then make a little nest out of pillows. Obviously, when the seatbelt sign is on, you need to get them up but otherwise, it means an extra seat for laying one of the kids down and the one on the floor gets a dark little cave. We generally manage for both kids to get 6 or 7 hours of sleep on an on a overnight flight which is excellent for maintaining good moods… Read more »

7 years ago

Great post, Emily! I have 2 boys (1 and 3 years old), and we travel to the UK from New York fairly frequently. You really nailed all the pros and cons and provide great tips. I would also say, with tiny children: fly in the morning! A night flight seems ideal because you think everyone will sleep, but nobody sleeps, especially not mom 🙂
Our favorite recent trip was renting a cottage in the country in Wales with very good friends of ours and their kids. (Like you said – the perfect equation: not a city, staying in a house, with other friends!)

7 years ago

great post! so many truths in here. one thing we decided a while back is to delay an urban vacation until the kids are old enough and more independent. our favorite types of vacation before kids was to book a trip to a big city and eat our way through it with trips to the museum, bars, and nightlife and lots of walking. we stopped doing that once we had kids. our vacations now are very kid centric. camping, renting a beach house, going on a cruise. and just fantasizing about our next trip to rome!

7 years ago

Love this post! Now that my kids are in the total sweet spot (ages 7, 9, 11), traveling is actually fun and easy. That probably started 3ish years ago when the youngest was 4 (just like you’ve noted). So my “tip” now is for parents in my stage: have some grace! When you notice parents of toddlers/young kids are trying their best, smile at them, offer some help, or politely ignore the behavior (whatever seems warranted at the time). Other people’s judgement, when I was trying my absolute best with a 4 year old, 2 year old, and baby, made flights 10 times worse.

Suzanne Baumann
7 years ago

Charlie is so cute it kills me! Especially that first photo of him sitting on the ground next to his roller bag.

7 years ago

We are traveling to Hong Kong this fall with our 4 and 2 year old and I am ultimately dreading the plane trip + their lack of schedules. I will definitely be using some of these pointers, thanks for this!

7 years ago

YES!!! This is a fabulous post, full of wise advice. I agree with everything, especially Success#1 and #2. Just go, but lower your expectations. We traveled to Italy when our girls were 1 and 3, lots of beach vacations (Puerto Rico, Maine, California, San Juans), and my favorites recently, Corsica (girls were 4 and 6) and the Dolomites (girls were 5 and 7). Absolutely rent a house and travel with friends. Best advice ever. And yes, grandparents too!! My only additonal advice, you can pack light!! I know it gets easier when they get older, but I have always tried to go minimal with packing (i.e goal of carry on only for trips, but I have not always met that goal). I used a ten dollar umbrella stroller, rented pack and plays or made sure the rental house had one already, and bought all the extra diapers/ wipes when we landed. There are grocery stores everywhere. Also, rental houses come with laundry machines!! I found my kids started playing with rocks and sticks and cups if there weren’t any plastic toys around (but also see above, have other kids around). Most importantly, it is your vacation, so plan the kind… Read more »

7 years ago
Reply to  Heather

I second the packing light thing! I can fit two adults, a baby and a four year old into two carryons plus two back packs. (We also have carseats and strollers in tow as well) I always look at the fools pushing around those enormous carts with a head shake (sorry Emily). No wonder vacationing is exhausting! I even pack the diapers because they free up space for the toys we buy while on the trip. There is an art and science to packing this strategically, so it does take a lot of planning. You basically pack, then Konmari that pack a couple more times. This probably sounds so obnoxious, I just learned the art and freedom of packing light in my backpacking Europe days and vowed to pull it off with kids as well. It is SO freeing. But a weekend at grandma’s house, three hours away. Heaven help us…we might as well rent a u-haul.

patty blaettler
7 years ago
Reply to  Emily

“We really are a spectacle.” That is hilarious.

7 years ago

Thank you so much for posts like these! Love the your thesis bit at the end. It is hard to remember to try to find balance between your needs and you child’s needs and all the guilt that goes with that. We traveled from DC to Hawaii with our daughter just shy of her 6mo bday and flight was great, vacation itself was hell.

7 years ago

I love this post! Can you share with us the ranch you rented in the valley? It sounds perfect!

7 years ago
Reply to  bradi

I second that! My in-laws live in Simi Valley, and I’d love a fun activity/place to stay nearby!

7 years ago

Traveled all over the world with great success with my first son. Now that I have two, the two vacation attempts we’ve made have left me in need of a vacation from vacation. I have to surrender to the idea that I need to stay in the US (likely) for the next four years, which feels like this ENORMOUS sacrifice (I know, I know). I would dare do Hawaii any day, but that is as exotic as it will get.

Also, my unsolicited advice on the TV issue: Free that thing (and you) up. Limiting it that strictly makes it way too powerful. My kid probably watches “way to much TV” but so did I, and I still love TV, and I still manage to be a creative, engaging person. My cousins who didn’t have a TV in the house ONLY watched TV when they were over at grandma’s house…so we never really knew them, but made great memories with the other cousins who had their fill of screens at home and therefore looked forward to play.

7 years ago
Reply to  Anna

Great tips Emily! I’ve taken a few plane trips with my now 22 month old (all before he was 1), there is NO WAY IN HELL I would take a plane ride with him now, so you are a SAINT for doing it haha. Can I also suggest a long kid-free vacation? Our close friends moved to France and got married last year, and we were in the wedding. Our kid was 9 months old at the time, and we decided to have both sets of grandparents come to our house and watch him (one set for one week, one set for another). It was AWESOME! We got some much needed couple time, and our parents got some great bonding time with their (at the time) only grandchild. My husband and I are now talking about taking a kid-free international vacation every few years, as budget allows. The kid(s) keeps their routine and comforts of home, you get some baby free time, grandparents get to spoil their grandkids….EVERYONE WINS! And I totally agree here with Anna about the TV. We super carefully restricted it, and he was OBSESSED with it and would completely melt down when we turned it off… Read more »

7 years ago

I just love this post – so real and true!! (especially the part of putting devices in front of them just so you can have a conversation at dinner or sleep a little – we’ve all done it!!) With our 2 kids, ages 12 and 6, there’s such an age span it can be tough. But we love going to the Mall of America – the kids can do the rides, it’s not hot inside the mall so no one is sweating buckets and grumpy, and I can get in a little shopping, too! But last summer we took a big vacation to Oahu with extended family – grandparents, cousins, etc. It. Was. FABULOUS!! We splurged to stay on the beach and just loved every minute of it and would do it again in a heartbeat – except for the awful flight (from Iowa, so no quick way to get there!) Good for you for continuing to travel and thank you for keeping it so real!!

7 years ago

My kids are 7 and 3 do I’m ALMOST there, but what’s becoming clear to me is that we took a lot of overly ambitious, ill-advised trips to prove to ourselves and maybe others that we were still people who traveled, when everyone would have been happier in Encino. That’s the main thing I preach to newbies, that there are seasons of life and this one that requires you to slow down and stay more homebound is so short. Like why did I take my 4 year old 3 month old to NYC for 2 weeks in a bad hotel room all together? We should have been hone in our jammies. And looking back, I wish I’d savored those “trapped at home” times a little more. (All the more reason design that makes you happy is important when you’re at home all the time!)

7 years ago
Reply to  Jenny

Yes, the element of “proving” kids haven’t slowed down my travel affects me too. And it’s insane. Family trips to local places have been by far the most fun and relaxing, so I need to just embrace it for this season of life and quit looking at Travelzoo.

7 years ago

The vacations you have planned sound great! You can do some more world traveling when the kids get a little older.
When we book hotel rooms we try to get rooms with suites. There’s more space in general, plus we can hangout/talk/watch TV after the kids go to bed.
The other thing we do is vacation with grandparents. Every summer we rent a house on the lakeshore with my in-laws. It’s so nice having the extra help, and they are always willing to watch the kids for a day or an evening so we can get out by ourselves. Plus it’s nice for the kids to have the extra time with their grandparents.

7 years ago

One additional tip we used last year when flying to Hawaii. Our 5 year old needed a car seat but I did not want to use one from the rental car place. I asked around and a friend had one in storage that she no longer needed, it was still before it’s expiration date, and she didn’t care about it – so we checked it on the flight over (wrapped in a large black garbage bag with bright string on it to help us identify it) and when we dropped the rental car off at the airport we left the seat there. Oh – and the best purchase we made for our daughter when she was too old for a big stroller but still too young for lots of walking is the McClaren umbrella stroller. Lightweight, folds easy, and was super handy in the airport when she was tired – we could just find a quiet area of the terminal to roll her around in and she fell asleep. We just gate checked it every flight – easy peasy! We took it to Disney with us and it came in so handy when we left the parks and had to… Read more »

7 years ago

I second the camping idea. I have three kids-8 yr, 7 yr, and 3 yr. We recently camped up through Indiana ending in Indiana Dunes on Lake Michigan. It’s so low-key and in keeping low expectations like you mentioned we all managed to have a good time. The kids made friends wherever we went and because we were outside we didn’t feel like we had to entertain them the whole time. We could RELAX too. I only wished we had been able to bring their bicycles-we didn’t have room in our van.

7 years ago

I flew with my 1.5 year old by myself and I upgraded to a bulkhead seat which has more leg room and no seat in front of me. It was fantastic… extra room without the cost of a full extra seat. And I wasn’t worried about her bumping the seat in front of me and bugging another passenger. She actually sat on the backpack on the floor for a while like a little chair. That was a win… me trying to use her car seat strapped to my luggage as a stroller… total fail!

7 years ago

#1 I totally forgot to bring toys once. Our daughter was 12 months old and we forgot to bring any toys with us to play with the entire time we were at a beach condo in Carlsbad. We ended up having to buy a ton of toys at the nearby Target just to occupy her while we relaxed. This seems so obvious but I guess we just thought we’d be at the beach all day and she’d be busy. We forgot about the evenings when we were making dinner or watching tv. #2 I just discovered that vacationing with friends with other kids was the most relaxing thing ever! My daughter is 6 now and she was able to run around with the kids riding bikes and playing games. Dads got to hang with dads, moms got to hang with moms, it was wonderful. It turns out camping near our house, even in the high desert heat was much more fun than a trip across the country with just our family of three in a hotel. #3 Whitefish is amazing. My dad grew up there and I’ve had years of memories there as a kid and as an adult. Always… Read more »

7 years ago

My kids are teens now but I have dragged them to 11 countries plus all over the US. I wish there was a a post like this when mine were young. It’s really comprehensive and would have helped me a lot. I have no problem letting a child binge watch an ipad on flights (oh how I wish that was an option for us back then). Plane flights are stressful for everyone involved and it gives the child, the parents and the other passengers a bit of needed peace. For me, the international trips were the hardest (for some reason harder to Asia than Europe). I always got them a seat for the extra space (yes the price can be a factor). Then my toddler or child had their own area to play and rest. I agree with you on toys. For the plane we always stocked up on inexpensive small items like matchbox cars, dolls or activity books. Then we wrapped each one like a gift so that took up a bit of time and added some excitement. You reminded me that for one condo we stayed at, I bought a box of toys from the goodwill and shipped… Read more »

7 years ago

Such a good post. Emily, can you please give information on renting that Encino farm house with miniature horses? I want to go there!

7 years ago
Reply to  Joanna

I want to know as well! I’ve been searching Kid and Coe and Air BNB looking for it!

Edan Lepucki
7 years ago

I like doing hotels if it’s not too expensive–getting two rooms, attached, is the way to go. That way, you can still have the hotel experience, and you all can get room service once, maybe do a breakfast buffet, watch some cable TV in a big bed, and then they go to sleep at their normal time, and you’re right in the other room, living it up!

7 years ago

Yes to all of this. I have an almost 3 year old (plus 2 stepdaughters aged 11 and 14 so basically free and wondeful babysitters that don’t require any actual parenting by me) so I’ve never experienced the insanity of baby + toddler travel. But I’m all about lowering expectations. This spring we had decided to splurge and do Maui–my husband’s favorite place. As you mentioned, hotels basically are a no go for us. The older girls need a room and I will go to dramatic lengths to avoid having to put the toddler in a room with us. We found these 3 BR condos that have access to a hotel pool and I convinced my husband we should just do it. But then flights were going to be $1,000 pp x 5. For four days. Couldn’t pull the trigger. I decided that since it was a relatively short trip, we really just needed warmth and water. We live in San Francisco (not warm) but Phoenix is a short and cheap flight away so I booked us a 2 BR suite at a hotel/waterpark monstrosity. Guess what? Toddler got sick on our first full day there and I spent the… Read more »

7 years ago

Just what I needed to read!!.. almost giving up on family vacations but this open up my eyes!..
Another great beach vacation is La Paz, Baja California, Mexico is like a big pull with no waves and beautiful little beaches !!!
Thank you will share this with my husband!!!

7 years ago

We recently took a vacation with our 3 year old and 9 month old. We drove 6 hours to get there, and the baby cried the whole time minus a couple naps and the 3 year old lost his mind and chucked toys at my husband who was driving. So, for the way home, we left a day early and drove at night. The boys slept pretty much the whole time and my husband and I got to talk the night away while we tried to keep each other awake. We felt crummy the next day after 3 hours of sleep, but it was kind of fun talking interrupted while the boys slept. Lesson #1 – traveling with kids suckkks unless they are sleeping ;). Then, we made the mistake of staying in a hotel during our vacation. It was real fun trying to get the boys to sleep in the same room and silently hang out trying not to wake them until we were ready for bed. Lesson #2 house rentals from now on. Lesson #3 – As Emily mentioned, staying in a place that has easy, walking access to the majority of your entertainment/food/etc. We spent 1/2 our… Read more »

7 years ago

Did you take a nanny with you on these trips? I thought you had one when you went to New York.

7 years ago

Years ago, when our kids were 1 and 3 we had to fly London to Singapore via Frankfurt. I was dreading it. My husband suggested I go on my own and he’d follow me on a different fligh a few days later. Bliss! He doesn’t get stressed with “what ifs” and doesn’t try to prevent/foresee situations. He handles them if they happen. Upon landing he said all had been good.
Now our kids are 8 and 11 and I’ve been traveling alone with them for a few years.
Other than that, we’ve bee through all of Emily’s win/fails and we travel just like she describes.
In UK we have family hotels that have toys, books, wellies, a free crèche, baby listening for kids AND a cocktail bar, candle light dining for adults. All rooms are big enough for 3-5 people, some are split rooms. Google luxury family hotels UK for more details. It’s great!

7 years ago

This post is totally right on. My kids are roughly the same age as yours and all I can say is AVOID CITY TRIPS. Spending a lot of money to sit in some crappy Airbnb apartment for your trip….it just sucks on so many levels. I am all for finding an awesome, big, kid friendly house near a beach/playground/farm and setting up shop there. Way better! Less stress!

Also, does anyone have tips about what to do with the freaking car seat situation on international flights? That was a big one we struggled with (we moved from the US to Australia when our first was 15 months…)

If you all come back to Australia, check out Umina Beach. There are lots of great rentals there and so much for young kids to do. And it’s maybe an hour from Sydney, perfect for your kid free solo outings.

I’ve bookmarked this post and so appreciate your perspective on traveling with kids. I love the baby/toddler years but cannot wait to travel with them when they are older!

7 years ago

Love this so much Emily. We travel from US back to Australia all the time to see my family. My best advice is pack light by borrowing anything and everything you can at your destination. My mum borrowed things needle we got there, and I called in a few favors from old friends too. A pack and play, high chair, a million toys, clothes, everything. I had everything for my son and I for 2 weeks in a small suitcase, a diaper bag and backpack.

7 years ago

First —
“I think because of that we have remained as happy and stressful as possible.”
I think there’s a typo there. Or a Freudian slip, your call.

Second, I used to work with a family whose child regularly saw a psychologist. The doc told them that vacations are good for developing neural pathways and making new connections. Often kids experience some big developmental gains after traveling, so you’re ALSO making your kids smarter!

We went to the Netherlands with an 18 month old, no separate seat, but we were in the bulkhead row, so he had a good amount of space to play with cars, stretch out, etc. Maybe a good compromise price-wise for those who can’t swing a whole extra ticket!

7 years ago

Loved reading this! Now that my kids are a little older (8 & 10), I have blocked out how hard it was at times travelling with littles. Our FAVE vacation spot we’ve been going for 8 years is on the Washington coast, Seabrook. ( We are in the Seattle area so it’s a 2.5 hr drive for us. We LOVE it there. Picture perfect beach village – everything is walkable… we park once and never get in the car again. We walk to coffee and donuts in the morning, walk to the beach, walk to the playground, walk for ice cream in the afternoon, walk around and admire the cutest houses ever, pretty much the whole vacay is centered around walking to fun places. The kids take their scooters or bikes and they love it. They do fun things like bike parades for kids – they give each kid a bag full of streamers + balloons to decorate their bike… feels like the 50’s or something:) It’s like Pleasantville. Our littlest learn to walk there and our oldest learned to ride a bike there. Happy memories and we always look forward to going back! There are dozens of adorable beach… Read more »

7 years ago

We live in Australia and have travelled to Europe, the UK, Asia and Canada many times with our kids to see family and explore. So nowhere is really close for us! It definitely gets easier and more enjoyable the older they get. With littles I totally advocate the beach holiday – they are happy to play, swim and eat and generally fall asleep at the end of the day tired and happy. Now they are older (youngest is 12) they are independent with luggage and on the plane. It is more about dividing time between something they want to do and something you want to do. It is a compromise but makes for a stress free holiday.

7 years ago

This past February we took our 5 year old and 8 month old to Telluride. I am the only one who skis in the family, so my husband went to ski school and I stayed with the baby and then I hit the slopes and he kept her. The 5 year old was in ski school for 3 days and did great. The last morning I decided to ski her. She was doing great – not out of control, talking to me the whole time, and then fell over and started screaming. Her ski didn’t release and there was a soft spot where her shin bone should have been. Yes – the only two hours of her young life that she skied with her mama she broke her leg. Snowmobiling and getting transferred in the van to the clinic in town was a huge ordeal. They showed us the X-ray, splinted it, told us she couldn’t put pressure on it, wouldn’t give her crutches, and told us to see a pediatric orthopedist when we got home because “it would probably need surgery” (thank God, it didn’t!). We got her back to the hotel and she would literally scream at us… Read more »

7 years ago

I have a 3-year-old girl and 4-month old boy, and and we learned a lot on trips with our daughter but haven’t yet tackled traveling with them both. Our biggest fail was on a trip to LA when she was about 2 – we learned that she gets carsick when she threw up all over herself and her carseat after a long drive to meet up with some cousins. We switched her carseat to forward facing (supposed to be less nauseating) and then took her on another long drive the next day, at the end of which she promptly threw up again. Huge parenting fail! Now we do everything we can to arrange our vacations to absolutely minimize driving, and if we have to drive, she gets kids dramamine and eats saltines the whole way. Smarter things we have done: 1) If possible have diapers and wipes from shipped to your destination to arrive the day before you do, that way you only need to bring enough for the day of travel plus some extras. We mostly stay in airbnb’s and every one of them has been totally accommodating about receiving a package. 2) If you have friends with… Read more »

7 years ago

Great post! I have a 3 1/2 year old and a 17 month old. We also love to travel and I agree with no big cities and pack light. Two of our best trips were Estes Park, Colorado and my most favorite we rented a cabin last month on a farm in Vermont. It was idyllic and just perfect. We helped with farm chores, went to town squares and played in the beautiful rivers. I highly recommend it and flying in and out of Boston to get there was easy. We often bring one car seat and rent one from the car rental place. You can also request car seats to be brought if you schedule limo airport pick up service. I did that in SF and it was so helpful. My last tip is to buy a car seat cover. It’s on Amazon and it’s a car seat cover with straps so you can wear it like a back pack. It also allows for toys and diapers to be thrown in there as opposed to your suitcase. It makes bringing a car seat so much easier. Best of luck with your future travels!

7 years ago

We got a boat this year in leiu of going somewhere. We live 15 minutes from an incredible lake and plan to spend every ounce of free time on it. We have a 9, 7, 4 & 2 year old. Maybe we’ll do Hawaii next year 😉

7 years ago

I love this post and completely agree. Although we’ve traveled a lot through the US and Mexico with my two little boys (and absolutely agree that friend trips and screen time are the way to go) we got brave last summer and decided to take the then 4 and 6 year old on their first European trip to Lisbon. Traveling with kids 4 and up is actually really wonderful. Probably because they have a great level of iPad focus that makes the flights relatively painless. I would not wish that long a flight with a toddler on anyone. Lisbon was amazing with kids and what really helped our fun was we stayed in one great, central apartment the entire week. Usually everyone tries to pack in multiple cities to a week or two in Europe but we took it slow. We were on Portugal time which meant staying up late each night – until midnight sometimes – to enjoy our dinners out. Because of that we wouldn’t leave the apartment until noon or later but that was okay because we stayed out the rest of the day. The city is super walkable with great and fun local transport, tons of… Read more »

7 years ago

Loved this post!! We travel with our kids and a few things i do…
1. For the plane: Wrap books, activities, etc like presents! Kinda of fun and takes up a few minutes. Then they are real interested in whatever was wrapped for a few minutes.
2. Order toys/activities to be delivered to your destination. Don’t spend a ton, you may end up leaving them behind but this way you don’t have to cart it to your vacation.
3. Sound machine…anything to drown out new sounds helps!
Thanks for everything Em! I think you are incredibly talented and relatable! Keep it up!

Nancy D.
7 years ago

Smiled at the Sunriver, Oregon picture! My husband and I (we are the grandma and grandpa) rent a big house in Sunriver for 3 weeks each summer and invite our kids and grandkids to come stay for as long or as short a time as they wish. It’s really a lovely vacation spot for all ages: golf, tennis, floating on the river, swimming, a lovely nature center (last summer the little ones wanted to go hang out there every day). Everyone bikes everywhere because everything is connected by bike/pedestrian paths. Such fun! We are available to watch the littles in the evening if their parents went to drive up to Bend for an hour or two (it’s only a ten minute drive and has good restaurants and an active outdoor scene). We like giving this Sunriver vacation opportunity to our young adult kids and their families instead of buying any big gifts for birthdays or holidays. Making memories rather than giving “stuff”. Makes me happy.

7 years ago

I like the way our family enjoys the trips together. We have the time to find out the new things, see the beautiful place and to share our feeling.
You had the exciting period, thank for sharing it.
Look forward to reading the article like this.

Alicia @FreshBabyGear

7 years ago

Bend is our absolute favorite family vacation spot and we go at least once a year, if not more (we live in OR). I haven’t been brave enough to get on a plane with my little one since she was 5 months and not mobile yet. Kudos to you guys and I sure appreciate the tips (we have #2 on the way)!

Sarah shumway
7 years ago

Love your list Emily. It’s bang on! My husband and I went to Italy 2 summers ago and decided NOT to take the kids. I felt so guilty but it would have been a shit show. All of the passengers were better for it:). I kept thinking what a mistake it sound have been to try to take 3 boys abroad with the schedule we kept. On the flip, we do low key vacations with kids. We’re doing a beach house in Oregon (my most fav of all) camping, hiking & site seeing in National park is in AZ/ Southern UT. We drive up the Northern Cali coast to SW redwoods & rent tree houses, all of the southern Cali theme parks, etc. we have 3 boys (3,7,11) and they all have various levels of abilities. We’ve cousin that picking something that offers them fun (outdoor or interest specific) and time with us is all they really want. The chance to have no set schedule, lots of talking, family games, friends if in groups and FAMILY time is all they need to be happy. I say save Paris/Rome & the other awesome adventures for the teenagers and adult kids. Jet… Read more »

7 years ago

Oh man, traveling with kids. It’s kind of the worst. But always worth it in the end. I agree with you on most of the successes and fails. But everyone’s different. I live in Hawaii, but my parents are on the mainland so I fly with my 3 kids (6 and under) a lot, without my husband. Red-eyes are the way to go for me. It’s so hard to keep 3 children happy and myself sane on a 6 hour flight during waking hours by myself. I guess I’m lucky because my kids do really well on red-eye flights. Takeoff usually puts them to sleep. I agree that lowering your expectations is the biggest key! You’re almost guaranteed to feel good about how things went if you start off expecting the worst.

7 years ago

Lots of great points here Emily. I have some suggestions for city breaks and road trips. We have nearly 3 year old twins who have been travelling since they were a few weeks old. We currently live in London (UK) and travel around Europe and back home to Australia regularly.

City breaks are doable but as you say it is a different trip than without kids. Research is key. Choose accommodation near a park/playground and plan your activities around parks and playgrounds. We only do one tourist thing a day and spend the rest soaking up the atmosphere. We find smaller or secondary cities are more family friendly – Lucca in Italy, Ghent and Bruges in Belgium, Brighton in the UK and Lyon in France are good examples in Europe. We use hotels on road trips when we need to stop for a night. Room service is amazing after a long day on the road.

Flying long haul is a whole other matter I spend days agonising over. iPads are a genius invention for this purpose and anyone who says otherwise can sit next to my kids on our next trip to Australia without one! ?