We just got back from a week-long family vacation and it was a big one—from Chicago to Maui. With the kids being 5 and 3, we knew the flights had the potential to be overwhelming for everyone. With that said, Hawai’i is special to us. It seemed to be the right time to share it with our kids. I couldn’t be happier that we did this trip. We all had an incredible time, it was enjoyable from beginning to end—even the flights!
I will say, just like anything, a little planning goes a long way. Thinking through what the kids would need + starting to pack the week before was a huge sanity-saver. If you’re headed out on a family vacation in the coming months, this post breaks down my process from beginning to end. I hope it’s helpful to you on future trips with the kids!
This is key. Don’t skip this. Start packing at least the week before. I know, it sounds bananas (and maybe it is), but unless you want to forget things, it’s a huge help to pack a little throughout the week leading up to your trip. It gives you time to think through everything you need for the kids and yourself. I was able to set aside all of the kids’ summer clothes ahead of time since they weren’t wearing them.
For the rest of the week, I kept a running list of everything else that we would need to pack closer to our departure. You can see my super fancy list below and get the idea. It’s simple but effective. Definitely write it down, there’s nothing worse than forgetting something!
In addition to packing our essentials, I put a lot of thought into the must-haves for our 10+ hours of travel. I think the advice of packing some new, novel items is always solid. But I’ll add on that it’s even more helpful to think about the more open-ended options. These are the choices that seem to get played with the most, which means the kids are occupied by them the longest.
I’ve bought my share of ’toys’ that have literally gone unused because there’s no creativity involved. Here were the top old + new open-ended carry-on items that I think your kids would make great use of on the trip:
The other useful thing to do is to grab one of the kids’ lunchboxes + fill it with snacks because, for whatever reason, flying makes kids ravenous. I try to bring along things that will be nourishing + filling because the carbs just don’t cut it for my kids in the long-run. These are the snacks that are reliable for our family:
When packing your bags for carry-on, remember that each person traveling gets a bag and a “personal item” (a large tote, by my interpretation). Don’t overpack your bags otherwise, it’s impossible to find anything. Instead, make an essentials bag with food and toys and your other bag can have extras like diapers and a change of clothes that you can keep in the overhead compartment.
Don’t limit your carry-on organization to backpacks/suitcases. Think outside the box and consider On our last flight, I even packed a separate cooler bag for drinks and snacks and it really freed up my carry-on bag space. The kids each have an insulated lunchbag that we clip onto their backpacks.
But if you need a little more space, I really like my Hydroflask cooler bag. This backpack option would be even more amazing if you’re headed out on a very long flight. Even though it doesn’t have adjustable straps, it’s great quality and your food will definitely stay cool.
Another ‘personal item’ that came along with us was a potty seat. Out three-year-old is relatively cautious of going to the bathroom in public spaces (they’re so loud!) so traveling with this made mid-air bathroom trips a lot less stressful. Ours fits great inside this Baggu cloud tote that we have.
And in case you’re in the market for new backpacks for the family, we all have State backpacks and I love them. They’re a perfect size + comfortable; mine is 5 years old and still looks brand new. Plus, for every backpack you purchase, they give a fully-packed backpack to an American child in need. (Such an awesome company, seriously.)
I also have one from Athleta that I love but it’s often out of stock!
It never hurts to throw the kids’ IDs or birth certificates into the bag in advance. We have seriously gotten halfway to the airport without them and had to turn back around. Pack them early. 🙂
Plan on dressing layers for the kids since there are so many temperature changes throughout the trip door to door. Bring a spare change in case of any diaper leaks or accidents…and maybe a spare shirt for yourself if you have room. I like to set these outfits aside the week beforehand so that they don’t get worn the week of the trip.
My son really likes to pick out his outfits, so it was a great opportunity to talk about the climate on the plane and how to plan for travel. He did a great job of picking out clothes that he felt great about that were also ideal of flying. It was an added bonus that when we got him up at 4:30am, we avoided any wardrobe crisis because he already had what he wanted to wear.
A day or so before you leave for the airport, quickly talk over your plan with your travel buddy. Deciding ahead of time who will wrangle the kids + who will manage the gear will help alleviate a lot of stress. Be sure your partner knows how to collapse the stroller (should you be bringing one along). If you got a special carrying case make sure they practice that too because this will be their job at security & the gate. My husband was never excited about practice ordeals, but they seriously kept things calmer whenever we got to the airport. Invest in your sanity, people.
Also, in case you’re not sure about which stroller to travel with, we have the UppaBaby Cruz (+ travel case) which I love for everyday + travel. I have a lot of friends that instead have the Babyzen YOYO and they swear by it.
Don’t forget to schedule in some time for yourself in the week leading up to the trip. It can be mentally exhausting to prepare and making time to rest and reenergize is key. I went to yoga at 8PM the night before our 4:00am wakeup and I was questioning whether it was the best choice. Ultimately, I was glad I did it. I got in some stretching ahead of a lot of sitting and was able to ease my mind. Even if you can’t get out of the house to move, some simple meditation, at-home yoga, a calm bath, or hot cup of tea can go a long way—definitely give yourself that time.
What stresses you out the most about traveling as a family? Are there any must-haves or approaches to preparing that have made traveling any easier? Share your thoughts below and head over to IG to follow our other posts about travel + family!
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