On traveling with (little) kids

I promise you'll laugh about (some of) it later, AND the best travel outfits that you will feel great in on the plane and actually wear on your trip

She’s BACK!

Well. Maybe. She’s trying. It’s been hard to get into some sort of groove with writing. Summer + new job + now back-to-school got me good! In true me fashion, instead of trying to get back into it with something simple and not too long, I went all in and decided I MUST publish this piece that I’ve been working on all summer…complete with answers to questions about traveling with kids from instagram and the chat. I hope you enjoy! I can’t wait to hear what you think AND what other tips you have to share with the group!

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I am by no means an expert traveler, but I have done a fair amount of traveling with kids - including long car rides (some more on the good, bad & ugly of recent and not-so-recent car trips here), short car rides, and long/multi-leg and short flights. I’ve done it with one, two and three kids. I’ve learned a lot along the way!

As a child, travel was a big part of my life. I was just a few months old when my parents took my on my first international trip. My dad grew up in Switzerland, and his parents, (my grandparents), his brother (my uncle) and his family, as well as many members of my dad’s extended family all live in Europe, and we visited them regularly. I haven’t ventured into this level of travel (yet!) with my kids - honestly just writing it out makes me feel very impressed with my parents - international travel with little kids is no joke!- we hope to be able to travel internationally more frequently as my kids get older. I think that my exposure to travel, and frequent travel in early adult hood (the first 6ish years of my career involved weekly/bi-weekly travel to whatever project I was working on) contribute to the fact that I am a very comfortable traveler, which helps me set the tone and also manage my own expectations a lot — both of these are keys for successful trips.

Whenever I share little peeks into our adventures, I get questions - ranging from specific (what pack n’ play do you use, what headphones are best for little heads) to broad (ie: what tips do you have for traveling with kids — if you are wondering this, please keep reading!), so, today, I want to share some of the best tips I’ve picked up along the way.

Kind of like meals, I like to think of traveling as a family as a practice. Every time we go somewhere, we are going to learn something new that makes the next time easier. And, we’re all going to get better at it - so, eventually, we’ll have kids that are comfortable traveling with us, and even by themselves some day.

To share as much as possible on this topic, I’m going to start with general learnings & what has worked well for us, and then also address specific questions I got from members of the chat.

I’m going to share (and link) specific products that we have and love, but I want to be very clear — there is no single product that is going to make or break your trip. There are so many products out there that are great, and I don’t want anyone to feel like you are just one specific toddler activity purchase away from a perfect plane ride. Yes - having a bag of tricks/toys is great - no, having one specific color wow book is not going to make or break your experience! There are a few categories I feel strongly about (for example, especially if you are traveling alone with little kids, a backpack is critical), but the process, approach & mindset (which I’ll get into), are all way more important than any specific item.

Also, one final reminder - many of the things that we have and use on our trips, we’ve collected over the course of 6+ years of trips with kids - we did NOT buy all these things in one fell swoop. Many of our purchases have been born from experience, where we learned we really do need something. Some tricky lessons (the memory of trying to break down our giant stroller and put it and our carseat in travel cases at gate check with my 8-week-old firstborn crying in my sisters arms while we were in the boarding line doesn’t haunt me at all, I promise!) but it does mean that we feel like our purchases are good ones & worth it (for us!) - otherwise it’s easy to fall into a trap of purchasing things that you may not use or need at all.

Let’s get into it!

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Setting (your) Expectations & Mindset (we’re not getting woo-woo, just getting honest)

Traveling with kids is not the same as traveling without them. It’s about a million times less relaxing. It is tiring, and hard. You are going to have moments of fun, and you will remember those good moments (I’ve found that this is a good mantra), but there are also going to be hard moments (hours/days/minutes that feel like hours or days). A hard truth is that we (we = adults) set the tone for how things go — our kids pick up on it when we are frustrated, angry, moody, etc. — and especially when you’re in a new or different environment, this has a huge impact. This is hard because when we actually are frustrated, angry, moody (or, when traveling - exhausted, stressed, frazzled, nervous, anxious, you name it), controlling our moods/not over-exposing our moods and emotions to our kids is one of the hardest things we have to do as parents/adults. But it’s true because it makes a huge difference.

I’ll give you an example — This July, we spent 12 (unplanned) hours in the Detroit airport with 3 kids as our flight home got delayed over and over again. How did my husband and I feel? Stressed, anxious, angry, exhausted. How did we manage to act? Not perfect, but through a combo of bathroom pep talks, fountain diet cokes, airport lounge cocktails, and taking some little breaks, for the most part we were calm, laughed as much as we could and accepted that being angry or mad wasn’t going to help the situation. Our kids? They will tell you that the time they spent in DTW having McDonalds Happy Meals on the airport floor & running back and forth through the underground tunnel were highlights of our vacation. (We are very grateful to the germ Gods that no major illnesses were acquired during this time ;)).

Proof of DTW fun!

This is extremely hard, but it will get easier with practice. It is also easiest to get started on this before your trip starts. In an ideal world, you discuss this with your partner ahead of time — what are each of you hoping for from the trip and what is/isn’t possible? How will you make sure that each of you get to do the one or two things that are most important to each of you? What are the things that are likely to be challenging on the trip and how might you prepare for them ahead of time? What was challenging last time that you can change for next time?

It is hard and exhausting to be an adult/parents and remember that adults set the tone! It is tiring! I often wish there was a reprieve from this responsibility. HOWEVER. There is some good news, and it’s that - when you summon the energy to be positive in the face of a shitty vacation experience (or, a morning after a not great night of sleep!) - the impact is immediate. Your kids will pick up on your vibe, and fast. This might sound silly but I find that trying to laugh anytime I feel like doing the opposite, actually helps.

Realistic Planning - INCLUDING Downtime

The theme of this piece is that traveling with little kids is not the same as traveling without them. This is particularly important when planning your trip — eg: the what are you going to do each day. Depending on where you are going, this might be very clear (perhaps you are visiting family & the routine of the week is agreed ahead of time), or up to you to decide (you’re visiting somewhere you’ve never been before).

Either way, when you’re planning, the best thing you can do is be honest & realistic about what you can do over the course of a given day or given week. I think you should err on the side of caution and DO LESS.

When we’re going either somewhere new, or somewhere where there are lots of things we could do (my husband grew up spending his summers in Door County, so there are so many things he wants to take the kids to do and explore when we are there), we like to make a list (we usually do it in Google Keep if you are someone who likes the nitty gritty of how it happens!) of the things we could/want to do, and then loosely assign 1-2 activities to each day, and also leave a couple days to do nothing. If we’re going somewhere new, we’ll save places to a Google Maps list, and then look where things are geographically. We haven’t gone anywhere where we have needed to plan a more detailed itinerary than that, or do major reservation-making ahead of time, so we always have the ability to pivot.

Think also about what YOU want to do. Shopping, a restaurant, seeing a site, hitting a museum, going to a workout class, whatever it is, pick the thing(s) and work with your partner to figure out how to make it happen.

Now that our kids are a little older, we also ask our kids what special thing they really want to do. A couple years ago when we went to Isle of Palms they were dying to go to the aquarium. On most other trips, they want to make sure we fit in a round (or 10) of mini golf. I like this practice because it reminds and shows us that family trips are about family trips - we ALL get to do something we want to do (even if we might not get to do EVERYTHING we want to do). AND, we all work together to figure out how it will fit into our schedule.

Managing the Routine

Since we still have nappers, we typically plan our days in two parts — we can do something big and exciting in the morning (the baby still takes a morning nap, but its much easier to skip it once in awhile now or make it very short. When she was a little younger, she used to take it on the go a lot), come back early afternoon for a rest/break/nap for whoever needs it, and then something again in the late afternoon/early evening.

We usually pick one thing a day— we’ll go do something in the morning and chill for the afternoon, or have an open morning and go do something fun after rest and then go out to dinner. And we mix it up — which is nice especially when you have a baby who might need a morning nap that isn’t on-the-go everyday. So if on Monday we went out all morning and the baby didn’t take a morning nap, on Tuesday we’ll try to let her get that nap before we go do something.

The rest period is critical for all of us. OCCASIONALLY we will skip it - like my husband will take the big kids to go play mini golf during rest time or something like that - but this happens only when we really want to. We = my husband & myself. The rest is critical for all of us. When we’re in a different place, and my older kids typically share a room, the time for the rest is usually shorter - closer to an hour than the 2 we like to have at home, but we do our best. We all need a little recharge in the middle of the day!

PS: I know that varying from your normal routine can be very hard, especially when that routine is connected to how much sleep you will get (and how your kids act — overtired kids (LIKE ADULTS, LOL) can be particularly cranky). Whatever you decide to do is perfect for your family, but I have always found that whatever we do on vacation (we usually get pretty lax) we pick back up in our normal routine when we’re back home with few issues.

Little Surprises

I always like to have a few tricks in my suitcase that can be pulled out when we just need *something.* These are just little things — something new to take as an activity to a restaurant (these stickers & books, plus the sticker refills saved me in Montreal when we had two big family dinners that went late into the evening), a little toy to play with if the supply at your Airbnb is low, coloring books, markers, a mini lego set. This is nothing crazy (honestly post-it notes & kid scissors have been a huge hit!), the helpful part is holding on to these things and bringing them out in a moment of need. You can find the perfect treasures on amazon, the target dollar section, TJ Maxx or Marshalls. I’ll pack a few of these on the plane too in case shit hits the fan!

Find a Babysitter

If there is ANY WAY you can get a babysitter — Do it. Go do something fun for a morning, or lunch, or in the afternoon, or make a full night of it. Check local hotels, ask anyone you might know in the area (this summer I found a babysitter when I posted that I was looking for one on my personal instagram and an old boss connected me with one of his family’s babysitters!), look for a local agency, ask family if you’re traveling with them. Go big and do it a couple times. It makes a big difference!

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Now to answer some questions directly from the chat:

I'm very interested in recs on the nitty gritty details of airplane travel. Like what do you use for packing for different ages, do you always check bags, seat selection strategies?

I will preface with the fact that we have always checked bags when we’ve traveled with all 3 kids, so I can’t speak to approach for carrying on. But, here’s my general packing strategy:

• 1 suitcase for the kids - either a large suitcase from target (I think it is American Traveler Brand), or a Medium Away. Each kid has a packing cube so all their clothes are together - easy for unpacking, packing up and putting everything away when we get home. Bring less than you think you need & make a plan to do laundry halfway through your trip (at least). On our most recent trip my son expressed interest in having a suitcase of his own. I think this was mostly because he saw a kid his age with a suitcase that converted into a scooter. We will see if that request comes back up again!

• Each of my older kids has a backpack in which they can pack their own toy selection (whatever they can carry). They usually each bring their Tonie Box, headphones, a selection of tonies, a book or two, and their stuffed animal.

• My husband takes a backpack as his carry on and he’s responsible for electronics. So, tablets, cords, etc. He also carries sound machines (we were very grateful to have these with us when we were separated from our bags after getting stuck in Detroit) & snacks.

• I pack a tote (Large LL Bean with Long Handles + Zip) that has our emergency backups. In this bag goes a change of clothes for each child, packed in a large zip-lock bag (dirty clothes then go right into the zip lock bag if anything happens!), a small selection of toys for the baby. A couple extra diapers, wipes, emergency snacks, a little zip bag of activities if the tablets don’t cut it (coloring books, sticker books, drawing pads, stickers, etc.)

• In the airport, we typically bring our travel stroller (we use the yoyo, and are deeply obsessed with it - when we’re not traveling our nanny uses it most days or it lives in our car. There are a ton of great options out there - but some things I love about this one - ease of fold, ability to carry over your shoulder with the strap, it fits under the seat in front of you on the airplane in a pinch, baby bucket carseat attaches to it (we have the nuna carseat), you can also add a ride-along board onto it. I put a stroller hook on it to hang my tote + a backpack when someone inevitably refuses to carry their own. I also wear a backpack (I really like my away backpack & would recommend it if you’re in the market. It unzips fully, making it very easy to pack and also get things in & out - it’s on sale right now!) that has everything I would need to reach while in my seat — in the small pocket I have my kindle, airpods, phone, corded headphones. I put a little travel toiletry case in it with all the baby things I need (pacifiers, pouches, a couple random toys, diapers, wipes, hand sanitizer, etc.) I like the hanging toiletry case because I can have that out, hanging from the seat in front of me, and get anything I need without digging through a bag - particularly useful if you’re going to have a baby sleeping on you. Also in my backpack: a sweatshirt for myself, my water bottle, anything else of my own things I want to carry (makeup, jewelry, etc).

• Our big kids walk to security (get pre-check if there is any way you can swing it), and we push the baby in the stroller. At security, we collapse the stroller, put the baby in the baby carrier, and then all our gear goes through. Then, once we’re through security, my husband or I keep wearing the baby, and the stroller is available either for stuff or for one of the bigger kids to sit in at any point. We always try to find a play area (or make our own) to get wiggles out before we board). I bring snacks but I also always let my kids pick something at the airport, because bribery does work.

• Board last. You don’t need a ton of time to get settled, you need to minimize time spent being forced to sit down as much as possible.

• On our past few flights we’ve sat either 3 and 1 in a row, or 2 & 2. We’ve been lucky to be able to get seats all in a row. Because buying tickets for 4 people is crazy enough, we’re avoiding buying 5 for as long as we can. So far, Willa has basically slept for the vast majority of every flight she’s been on, including our most recent trip when she was ~13 months. We’re flying internationally this December and she’ll be 18 months and I think that’s just a very hard age to fly with and there’s not much you can do about it - just grin and bear it and know that the plane ride always ends. I’m hoping that this will be a good time to give Miss Rachel a shot!

Sleeping arrangements! I know you shared the Slumberpod on Insta. Anything else parents do with multiple kids if you can’t get an airbnb/house?

Our sleeping arrangements very depending on where we are going, but our ideal setup is 2 rooms - one for the older kids, and one for my husband & myself + the baby. When possible, we use the slumber pod so that the baby can have her own space & we can also be in the room without worrying about bothering her with lights or waking her up. I pack it in the kids suitcase and will happily forgo other items in order to have this.

We did do adjoining hotel rooms a few years ago and the two big kids had one room and we took the adjoining room. It worked fine!

How can we plan fun for everyone with a mix of ages (including when you still need to plan around a nap time)?

It is hard to manage kids of different ages and to feel like your whole schedule is dictated by “The Schedule.” The good news is that this doesn’t last forever! I addressed this a bit indirectly already, but we manage this by anchoring on the major rest time of the day for most days, which we all “observe” even if we don’t all nap. We tend to divide our days in half, and whenever our youngest is taking multiple naps, at least one would be a crib nap. Then, some of the days, we just don’t worry about it and assume that anyone who is tired will fall asleep and we’ll just roll with it. We like our schedule, but when we’re away, I don’t worry about it too much & we’re always able to get on track when we’re home.

Also, allowing everyone (who can articulate an opinion) to get to choose something they want to do helps with this a lot - then we work backwards from everyone’s pick so that we know that we’re hitting all the big stuff!

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So, how does this all tie in to getting dressed? Well, I had a LOT OF TIME to think about my choice of outfit for a day of travel home, as I ended up wearing my outfit for 3 full days (and sleeping in it too…good times). I always put careful consideration into what I’m wearing when I’m traveling because I want to feel good, and also be comfortable, and also wear things that make sense for my entire trip (and not just the travel portion!)

A shower and clean clothes after our trip felt absolutely incredible, but I wore a variation on my typical travel formula, and it delivered in every way I needed it to, and in even more ways than I had ever expected.

This gal had no idea what she was in for (although my closed eyes in this photo suggest that perhaps I knew it on a molecular level)

Regardless of where I’m going - there are a few “guiding principles” I follow when selecting my travel outfit. These rules can guide you to the perfect travel outfit, for whatever type of trip/destination you have coming up.

1. Comfort - Comfort is king. Always & forever. Especially when traveling. Unless I am heading straight to a meeting, I am wearing elastic-waist pants, and closed-toed, walking-friendly shoes (usually sneakers).

2. Layers - airplane and airport temps can be unpredictable - you never know when you’ll fell chilly. If you’re wearing a long sleeve shirt, wear a t-shirt underneath.

3. Versatility - I wear pieces I’ll wear at my destination. This means I alway like what I’m wearing. And, by default, if I’m stuck wearing it longer than expected, I don’t feel like I’m wearing something grubby or that doesn’t fit right.

4. Essentials at arms length - even when checking, there are a few things I always make sure I have in my carry-on. A small toiletry pouch (sunscreen, lip gloss, deodorant), my jewelry, my makeup pouch, and a change of clothes for my kids.

You never know when you might end up wearing something you planned to wear just to travel for multiple days - hope for the best, but make sure you’re prepared!

Here is some inspiration for your next travel out (or, honestly, just outfit!), no matter what your destination might be, or the purpose of your trip it. (You can find all pieces featured here).

Sweater Tee / Sneakers / AYR High Hope Pants / Sunnies / Sweater / Tote Bag

This is my standard “recipe.” It could work for any trip, any destination, any co-travelers. This is honestly just a “works for everything” type of uniform that I can just default to any time I’m not sure what to wear! These pants are incredible!

Blazer / Socks / Loafers / Pants / Polo Sweater / Tote

If you are traveling for work and heading straight into anything with co-workers, or anything client-facing, deciding what to wear can by tricky. These pants are my tried-and-true — they hold their shape, are formal enough, but are also extremely comfortable. I like to have layers on a plane, so I’m going for a long-sleeve and a blazer, but you could play around with this depending on the formality of your workplace.

Tee / Hat / Pants / Sweater / Tote / Sneakers

This is about as low-effort of an outfit that you can come up with. I’m currently deeply into the combo of a dark blue and olive green with any kind of pop (in this case its the bag, but it could be anything), and so I am carrying that color story into this outfit. The Donni Rib Knit Kick Flares are GOAT in my book, and you can wear them on a plane, and out to dinner, and with a blazer, and to walk around all day long, and the list goes on.

Sweatshirt / Sneakers / Pants / Button-down / Backpack

Another color story that I am very into right now (red/burgundy and blue), translated into an easy outfit fit for travel. The sweatshirt is your comfort piece for your trip, the pants will work to be dressed up or down, the button-down works with jeans, skirts, over a dress, etc.

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Okay! That’s all for today. I would love to hear from you in the comments — what am I missing, what other tips do you have? What questions sould I answer in a part 2?

Also, if you’re looking for more travel on kids info, you might like:

• “International Travel with a Toddler” by my friend

  Tory Stroker

• “Things for Traveling with Kids that we Can’t Do Without” by my friend

  Ellie - A Day In Her Life

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