February 4, 2019

Traveling with a Toddler & What Worked For Us

Traveling with a Toddler - Tips and Tricks

A little over two weeks ago, I was meeting Sai, Olivia and Krystal for dinner. At that point, I was itching to escape the cold for a few days and I knew that Keith, who is smack in the middle of his busy season (he was doing the sound on a couple of movies that were premiering at Sundance), was unable to really travel anywhere. Of course, I always want to go away with my husband and family, but I’ve never been one to turn down a girls trip. Randomly, I asked the girls if they’d want to take the (baby) boys and take a little getaway. I didn’t expect such an eager “hell yes,” thinking everyone had plans or things going on, but luckily, everyone was game!

We warned Krystal, who was the only one without a little child to care for, that this trip would be anything but relaxing and she may want to sit this one out! Because the reality is, if you’re traveling with three little kids who are not your own, things will get annoying…… really quickly. The trip ended up being such a special one, but between three boys under three, we had our fair share of  meltdowns and fires to put out.

At this point, I’ve flown with Nate several times and this time around, he was easier than ever before. He’s a few months shy of turning three and I swear, it’s made such a huge difference in his maturity level, his patience and being able to reason with him. He’s always been such a cool, calm and collected kid, but with any child, traveling can be tricky. Especially if you don’t have a second set of hands to help you out. It was just us three and our three boys so we had to get a bit creative. However, thankfully, it was as smooth as we could possibly hope for.

Traveling with a Toddler & What Worked For Us:


Lots and lots of snacks! I packed MadeGood granola balls, Almond butter and jam sandwiches, crackers, fruit, cookies and as an extra special treat in a dire situation – lollipops and gummy bears. Nate does not have candy often, so I wanted something extra special for a high pressure situation.


Stickers are such a lifesaver when flying, in restaurants or anywhere where you need a few moments of pure distraction. I got this pack from amazon and it’s always such a hit because it comes with so many stickers. Just make sure you bring some paper or coloring books to be able to stick on. There’s also so many reusable Melissa & Doug sets, which is perfect to peel on and off plane windows. Always a favorite of ours!

Coloring Book:

This kept him busy for a good 40 minutes- a priceless amount of time when traveling with kids or again, in a restaurant.

iPad & Headphones:

We loaded up our iPad with some of Nate’s favorite shows including Peppa Pig, Bubble Guppies & Daniel Tiger. This was the first time we used headphones and they were such a hit. We used the combo with this rubber case. For the plane ride home, we took the plunge and purchased Moana from iTunes (on this trip, Nate watched it with Sebastian, Olivia’s son, and he loved it so much). He’s never really watched a movie, but I think he may be ready to watch a movie in its entirety.

Tip: if you’re using a newer iphone/ipad, don’t forget to bring an adapter for the headphones!

Travel Activity Pack: 

Lastly, I ended up ordering this activity pack and it came in such handy during the last hour of our flight. At that point, he started getting so antsy and was over the iPad and everything else. I busted out a few things from this and it kept us busy until we landed. I still have a few things leftover for the return flight home.

Travel Stroller:

I’ve written about our travel stroller(s) in the past. We have two, the Mountain Buggy and the BABYZEN YOYO; while the BABYZEN YOYO costs a lot more, it’s incredibly compact, easy to maneuver and such a smooth ride.

Tip: Make sure you get stroller hooks so you can easily attach your bag at the airport! 

Crossbody Handbag:

Lastly, the night before we left, I started packing my Jumbo Chanel to take on our trip. Not sure what I was thinking as that would completely eliminate the use of one of my arms. Luckily, I came to my senses the morning of our trip and transferred everything to a crossbody bag. Don’t get me wrong, I still had my hands extremely full, but if I ended up with the other bag, it would have been even more of a balancing act.

Did I miss anything? If you have any questions, leave it in the comment section and I’ll be sure to answer and/or edit the post to add them in!

Also, if you’re a pro at traveling with small children and have any tips to share, please do!

If you missed it the first time, here’s the post on our first time traveling with Nate.




  • Rena

    How cool that you finally travelled with your girls and the kids! And your tips are sounding very good. Thanks for sharing.
    xx from Bavaria/Germany, Rena

  • Roses for Fridays | by mia

    Patience is a virtue when traveling with young kids … you certainly got what it takes Beautiful!

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  • Ann


    Great post. What brand crossbody did you use? I’m looking for a good yet stylish one when traveling w kids

    • Helena

      I almost feel silly writing this, but I just use one of my smaller chanel bags! That’s really the only one I have that’s a cross body, so it’s always the one I reach for.

  • Young

    I’m glad you were able to go on a little getaway trip. These are great tips!

    The Style Intermission

  • Janine

    Oooh how fun that you got to take a little trip with your girlfriends AND all of your baby boys!! That photo is absolutely adorable hahaha!
    Great tips you shared here! I got my baby nephew a coloring book last Christmas and he loves it, his mum said this is the first time he ever used a toy for longer than two weeks.
    xx Janine

  • Jessie

    We booked a red eye flight to Europe with my two year old son years ago thinking that he would sleep the whole time. He didn’t close his eyes once! He was really good though (shocking, I know) and we did bring an iPad with us which distracted him. I was pregnant at the time and I swear I got the vapours worrying what people were going to do as we were basically trapped for 8 hours. I think its great to take them places – often – so it is normalized, For the rest of the people on the flight, that’s what noise cancelling head phones are for, lol. Instead of a cross body bag, I had a LV back pack -both hands were totally free.

  • Anne

    We almost never traveled with a stroller (we did once, but we checked it underneath the plane), and instead always carried our daughter in our Ergo carrier. This keeps your hands completely free and you don’t have to take kids out of carriers to go through security, which is amazing since you don’t have to worry about wrangling them in the security line. Once she was one, we started carrying her on our back instead of front, so everyone was more comfortable. We traveled all over China for two weeks with her when she was 2 completely in the Ergo. We did this until she was 3, and then we went stroller and carrier free. Our awesome nanny got her out of the stroller and walking long distance all over Brooklyn when she was really young, which was a game changer!

  • Francine

    Major flashbacks reading your post. All very proven tips, so well done!

    We traveled to Maui with our three boys – they were 7, 3 and 3 at the time. It’s a relatively short flight (4 hrs from CA), but the amount of s**t we brought for them…we called it “Preventative Packing”. We also take a LONG road trip (9-10 hour drive) to Lake Tahoe every summer. One year, again when the boys were young, my husband packed a Home-Depot-sized bin of Thomas trains and TRAIN TRACKS. Yes, wooden TRAIN TRACKS!! We still joke about it to this day. But hey, better safe than sorry!

  • Chantal Caissie

    Where did you go!?

  • Gayana Bagdasaryan

    this is such a useful post! Thank you!

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    I agree with your travel with toddlers is a very happy moment of life. ts a great to do. When kids play with toys they did very creative things. I feel their pleasure with my heart

  • evelyn fuentes

    i will be traveling with a toddler was wondering how do i do to have her watch her favorite shows on her ipad like pepona pig and others please help thank u


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  • psychology Willetton

    Great tips. Distraction is definitely key. Having some photos of where you’ll be staying, where you’ll be going etc may also help

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