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10 Tips for Traveling with a Toddler

I haven’t counted for sure but I think it’s safe to say that Leo has been on close to 30 flights … and trust me, while he is a pretty good little traveler, not all of our flights have been rainbows and sunshine. For example, on our way back from Maui we honestly had one of the WORST flights with him … he was tired and cranky and not feeling well, and I was exhausted and uncomfortable … everything was going wrong. I forgot to pack milk for his bottle, my water exploded all over everyone, he was squirming and squeezing before we even took off… I was hot, sweating, frustrated, and on the verge of crying … before we even took off! LOL … it definitely put a damper on the end of the trip and at that moment I felt like I never wanted to travel with him again. I honestly don’t know how people can do it all the time … no matter whether you’re traveling with 1 or 4 kids (omg 4 … ?), it’s a struggle.

However, struggles, breakdowns and tears aside, I feel like I have had a good track record and a PRETTY good system when it comes to traveling so today I thought I would share some of those tips and insights with you … along with a few of my favorite products to travel with! I will warn you though … no matter WHAT products you bring with you … you might still have a shitty flight no matter WHAT stroller you have, but hell, at least you’re trying to make the trip as smooth (and easy) as possible on you and your little one!

Here we go!

Jillian Harris A Week In My Closet

1. Do Your Research

When I search for a flight I always start by sorting my options from least expensive to most expensive, once I have the cheaper flights at the top, I then look at the hours of travel and sort by shortest duration … sometimes you can get the shortest duration for only $40-$50 more than the cheapest flight (WORTH IT!!). Sometimes there can be a larger difference in price between the cheapest and the shortest duration with the least layovers and I always ask myself if it’s worth it to spend $200 more on a shorter flight and 9/10 the answer is hell yes … especially when traveling with a child!

When we went to Hawaii, we had to get a hotel room on the way there and on the way back … to me, it just wasn’t worth the savings … we had to haul everything off and onto a shuttle, check into a hotel, set up the crib, find milk, yadda yadda yadda … you know the story. TRY TO AVOID OVERNIGHT CONNECTIONS AT ALL COST!!!!

2. Invest in a Collapsable Stroller

One thing I’ve learned while traveling with Leo is that most airlines won’t allow you to bring a stroller to the gate if it’s a 2-piece stroller, they make you check it!! ?? Trust me, you don’t want to be left without a stroller while traveling with your kiddo … you want to be able to strap them in as long as you can (without having to carry them everywhere you go!). We invested in the Bugaboo Bee stroller and we love it … I’m sure there are lighter, and more compact strollers out there but I’ve found that this one is super easy to travel with, it’s sturdy and collapses easily!

3. Purchase a Cell Phone Holder

A cell phone holder for your stroller might seem excessive but you won’t regret having this accessory because it allows both of your hands to be free! I know some of you might just toss yours in your bag but I like to have mine out so I can easily see if there are any updates on our flights (another tip is to download your airline app so you always get notified if something changes!) … plus, it also doubles as a great selfie stick to document family trips! LOL!!

4. Get the Damn Car Seat Bag

I always watch families check in their car seats, they bag them up in plastic bags which takes forever and then they are awkward as hell to carry around!! I knew I didn’t want to be stuck struggling with this so Justin and I caved and bought the car seat bag (which is only around $40) and it’s a game changer! It’s so easy to slide onto the car seat and it has handles which make it a breeze to carry! When I travel alone I am able to manage my suitcase, the stroller, and the car seat on my own without a luggage cart!

5. Don’t Skimp Out on Your Suitcase

I invested in an amazing suitcase years ago (I’ve had it since my days on The Bachelor) and it was one of the best investments for traveling ever, it’s a suitcase from a company called Briggs & Riley and they have a LIFETIME guarantee! I’ve had mine repaired twice and they are so good about it, all you have to do is give them a call and they find the local repair shop and you can take it right in to get fixed for free, no questions asked! At one point, the damage was so bad, they just sent me a BRAND NEW suitcase!!

Jillian Harris A Week In My ClosetJillian Harris Happy 30th Birthday Justin

6. Organization is Key

I like to pack Leo’s clothes in my suitcase when we travel and I find the easiest way to do this and to keep everything tidy and organized is by using the collapsible storage compartments from IKEA! I keep all of Leo’s clothes in the compartments and once we get to our final destination, I take them out of my suitcase so to separate our clothes.

7. Don’t Forget the Snacks

I try to pack lots of snacks when I travel with Leo because it’s a great way to keep him happy and entertained … plus, there aren’t many plant based healthy options for food at the airport and I don’t like the idea of giving him french fries all the time so I like to pack pouches, gummies, granola bars, fruit slices, etc, for him to eat. The little spill proof treat dispensers are great too because it keeps them busy picking out one cheerio at a time while I breath deeply into the back of the seat getting any chance of quiet I can … LOL!!

Jillian Harris What I Learned Travelling to Europe with LeoJillian Harris Trip to Europe Jillian Harris Trip to Europe

8. Hydrate!

I have a Thermos Straw Bottle that I like to bring for Leo, I’ll fill it up with water for him and sometimes (depending on what time our flight is!), I’ll fill it up with hot milk if I know we are going to be landing late. Before you take off on your flight, keep in mind what time you’ll be taking off/arriving and plan ahead for what your child might want at those specific times!

9. Backpacks are a Must

I know I’ve talked about this a LOT but the Fawn Design Diaper Bags are a lifesaver!! At first, I didn’t think I would like having a backpack, I thought I would want to have a tote that I could grab things out of easily but it turns out that the backpack is so much handier! I keep all of my important items in the front zippered pocket so they are easy to reach and there are so many great compartments within the bag that keep everything organized. I love the fact that these bags are vegan and come in a bunch of different colours … not to mention, they’re durable … mine has been on over 30 flights … it’s been spilled on, puked on, kicked around, you name it … and it STILL looks like it’s brand new!

10. There’s Always Wine

I always joke that wine is always the way to go when you’re on the plane but there have been times, like when Leo and I travelled to Austria and I had a few glasses of wine on our flight and immediately regretted it because Leo didn’t sleep at ALL so if you know it’s going to be one of those flights … skip the vino … but sometimes it does help to relieve some stress! LOL!

Jillian Harris Trip to Europe Jillian Harris Trip to Europe

What are some of your favourite travel tips?? Share them with us below!



Leave a Reply

  1. I would add to this list:
    1. If they have a stuffy, take it away before you have to send it through the scanner. My LO melts down on this all. the. time.
    2. Avoid shoes with lights in them for your LO while travelling as you have to remove them for security. If they have regular shoes, you can leave them on and make things a little easier for yourself!

  2. Your post came at the perfect time! We head to Maui with our 16-month-old daughter in two weeks. She has also been on a lot of flights, but not since she has becoming so mobile and opinionated! Well, that’s a nice way to put it:) Do you have recommendations for keeping her happy/entertained during the flight? Oh, and thanks for all that you do. I love your blog!

  3. Any tips for in-flight activities? I’m traveling from Edmonton to Maui with an 18 month old and dreading the 6 hours. I wish I could travel first class!!

  4. Awesome article! We are planning a trip for the summer and it will be my toddler’s first flight. Do you have any recommendations for take off and landing for the pressure?

  5. Where did you get Leo’s “explore” jacket? It’s adorable and I would love to get one for my little boy!

  6. I try to incorporate little activities every 30-45 mins. Colouring, puzzles, a walk to the bathroom- anything to change it up and keep him interested. We ease up on screen time too, downloading some of his favourite learning games and Netflix shows. He is 4 yrs old. Lots of snacks and water help too.

  7. I hate airplanes due to all the germs – I load up a ziplock bag with a diaper, some wipes and a disposible changing mat. These are made into kits that could just be grabbed and everything is disposible.. I know its not environmentally friendly.. But planes are dirty and i am not using a re-useable change pad on a plane… I have used this system a few times and its worked amazingly…. Store a few in the seat pocket in front of you, grab and go when you need them… Happy Travels.. Love the backpack idea…

  8. Jillian, I have a question about the car seat bag! Did you get a universal bag or was it specifically made by the car seat manufacturer?

    Thanks for sharing this blog! I’m contemplating a trip soon with my two little ones and this gives me a little more confidence!

  9. Totally want to apologize for calling you out in the PHX airport. Mom to mom, no one wants to be bothered that early especially with a child in tow. But thank you for being so nice and taking a second to chat. So glad you wrote this post, I wanted to go back and ask you what stroller you were using that day, so thanks! Keep doing what your doing Jillian, your an amazing mother/person, love all your posts! And next time your in AZ I’ll tell you where the best chips/salsa and margaritas are, that’s plant based right ha!

  10. Jillian we need your help!! We’re in Hawaii now for a week and can’t get our toddler (21 months) to sleep past 3am! ? since you were just here do you have any tips for us!!!??? #helpplease

  11. I would love to know what you do for Leo for a sleeping set up when you are travelling. My son is the same age as Leo and is obsessed with his crib and will not sleep with me which makes me so scared to travel anywhere! How does Leo sleep when you are travelling?

  12. Great tips! Thank you. If you are renting a vehicle when you travel you can request a car seat so you don’t have to pack that thing around. That’s what were doing for our trip to Kauai next week.

  13. Leo is the cutest little boy!! he looks just like you Jillian, so adorable! I only have 1 tip.. take lots and lots of photos and videos..!!!

  14. You mentioned bringing gummies as a snack. What brand do you get for Leo?
    I have a son the same age.

  15. Ah yes, even with the best laid plans, travel can be unpredictable and when you add kids … even moreso. Thanks for writing this blog with your tips.
    I have a tip … rather that spending your precious time scouring the Web for what is hopefully the best flights, accommodations, car rentals etc – why not connect with a travel agent and describe the experience you’d like to have and then let her take her experience, training and expertise to tailor a trip just for you. The personalized service cannot be replicated by an online booking engine before, during or after your trip.

    1. Does anyone have any suggestions on using a car seat on the plane for a 2.5 year old? From what I understand it’s not mandatory. On one hand it seems like a friggen nightmare.. on the other it doesn’t feel right not using it regarding safety. Help!! Lol

  16. a little trick we use is buy a few cheap toys (dollar store is ideal) and wrap them. Throughout a long flight you can let the kids unwrap a toy to give them something new to do.

  17. If I remember correctly, you splurged and upgraded your seat when you went to Europe awhile ago. Was it worth it? I’ve wanted to fly first class FOR SO LONG and now that we have a wee one on the way and we are going back to France to visit family in June I’m thinking this may just be the time that I crack and do it. Babe will be about 4 months old by that point. Worth it? Let me know!

  18. Hey.

    could you do a blog post on travelling with a 9.5 month old to hawaii!!!

    we don’t know about carseat in airport. we didn’t buy a seat for the baby so worried about that. what you would need in hawaii. if renting a car if you rented a carseat. etc etc etc


  19. Any tips for in-flight activities? I’m traveling from Edmonton to Maui with an 18 month old and dreading the 6 hours. I wish I could travel first class!!

  20. I know this is an old post but just wanted to say thanks for the tips! I am flying with my 18 month old later this month – I am panicking already because he can’t sit still for more than a minute. This makes me feel like we will be ok!

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