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Article: Over the River and Through the Woods: Holiday Travel Tips for Families With Little Ones

Family packing a stroller, toys, and kids’ clothes for holiday travel
flying with a baby

Over the River and Through the Woods: Holiday Travel Tips for Families With Little Ones

Grandma’s house, the cousins’ place, the big family dinner three states away. The holidays have a way of putting families on the road, and when you’re traveling with little ones, the trip itself becomes part of the adventure.

We’ve been helping St. Louis families get ready for the season for nearly 30 years, and we’ve picked up a few tricks along the way. Whether you’re driving across Missouri or catching a flight to see family, here’s how to make the journey a little smoother for everyone.

Pack in Layers (Literally and Figuratively)

Holiday travel means changing temperatures, from a chilly morning departure to a toasty living room full of relatives. Dressing kids in easy layers lets you adjust on the go. A soft long sleeve under a zip-up hoodie or cardigan works for almost any age, and you can peel off or add on as the day changes.

Pack by outfit rather than by item, and roll each one together so you can grab a full change without digging. Always keep one spare outfit in your carry-on or front seat bag, because spills, snacks, and surprises don’t wait for the next rest stop. And if there’s a family photo or a dressy dinner on the schedule, pack that outfit last so it stays on top and wrinkle-free.

Bring a Little Piece of Home

New places can feel exciting and overwhelming at the same time, especially for babies and toddlers. Familiar things help. Their favorite pajamas, a beloved stuffed animal, or the bedtime book you read every night can make a strange room feel cozy.

Try to keep a few anchors of your usual routine, like the same bath-book-bed rhythm at night, even if the timing shifts. You don’t need to hold onto the whole schedule. A couple of familiar steps go a long way.

Make the Car Ride Part of the Fun

Road trips with kids are all about pacing. Plan stops every couple of hours for stretching, snacks, and a little wiggle time, and build extra time into your arrival estimate so the drive feels less rushed.

A small bag of new-to-them activities can buy you miles of peace. Board books and picture books for the little ones, chapter books for older kids, and OOLY art supplies like markers, sticker books, and journals keep hands busy in the back seat. Save a surprise or two for the last stretch of the drive, when patience tends to run thin.

Flying With Little Ones

If you’re flying, a lightweight stroller or a comfortable carrier makes moving through the airport much easier, especially with bags in tow. Every airline handles strollers a little differently, so check your airline’s policy before you go.

Pack a carry-on with everything you’d need if your checked bag took the scenic route: a change of clothes for your child (and one for you), snacks, wipes, a couple of quiet activities, and any comfort items. Dressing kids in comfy, easy-on clothes makes security lines and airplane bathrooms a lot less stressful.

Staying at Someone Else’s House

Being a houseguest with little ones works best with a quick conversation before you arrive. Ask about the sleeping setup, any pets, and whether there’s a spot where your kids can play. A few toys or a puzzle from home gives them something familiar to settle into while the grown-ups catch up.

It also helps to agree on a rough plan for the visit. Knowing when the big meal is, when people tend to head to bed, and when you’ll have quiet time makes it easier to plan around naps and early bedtimes.

The one thing that matters more than any list

Give Yourself Some Grace

Here’s the truth: something will probably go a little sideways. A nap gets skipped, a snack gets dropped, someone melts down right as you pull into the driveway. That’s okay. It happens to every family, and it doesn’t mean the trip isn’t worth it.

The memories that stick are the ones from the destination. Cousins playing on the floor, grandparents meeting the baby, a warm dinner surrounded by people you love. The travel is just the road that gets you there.

Get Ready to Go With Kangaroo Kids

Before you hit the road, stop by the shop or browse online for everything you need for the trip. Comfy travel outfits and cozy pajamas from newborn to size 12, strollers and carriers, books, toys, games, and OOLY supplies to keep little hands happy. Every piece is one-of-a-kind, and every purchase earns rewards points.

Safe travels, friends. We hope your holidays are full of good company and short lines. 🦘

SHOP ALL

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