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10 lessons from 10 years of traveling with kids

Dec. 24, 2019
12 min read
Hawaii Hike
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When I first began the journey of sharing family travel stories on the internet, I had a 1-year-old. We were fresh off a big multifamily trip to Disney World and had gotten there on Southwest award flights with a toddler, and I wanted to share the few things I'd learned with others considering the same type of trip. The Mommy Points website was born, and so was my life as a family traveler.

This week, my oldest daughter hit double digits. Gulp.

With a solid decade of good, bad and ugly family travel experiences now forever etched in my family's hearts and minds, here are the top 10 things I've learned about traveling with kids.

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Don't book newborn travel until you meet your baby

"My life won't stop when a baby arrives. I'm going to keep doing all the same things as before, just with a baby happily strapped to me."

Yeah, I said those things. I'll wait while everyone gets in a good laugh.

Yes, life goes on once a baby is born ... eventually. But every baby and birth experience is different, and some are really, really tough. Some little ones cry for much of the first year and hardly sleep (looking long and hard at both my kids here). When you're surrounded by nearly constant screams and little sleep, travel is usually not a great fit, at least for that phase. Things will get better, but don't fully commit yourself to big trips with a newborn before you've even met him or her.

That said, traveling with a 3-to-6-month-old can be a sweet spot before things get tougher with a squirmy toddler, but not every baby is a happy ball of rainbows at that age. So, take it easy on yourself with the "things won't change" expectations. Change is OK -- you'll get back to your far-flung ways soon enough.

It's OK if your kids don't remember the trip

When your kids are really little -- as in still babies -- travel's really about where you want to go. You don't yet have to tailor your trips to places that dump buckets of slime or have a kids club. They're just along for the ride. As babies turn into toddlers, it can be helpful for the destination to have something fun for them to do, but they still aren't going to truly remember the trip. And that's OK.

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It's fine to watch little ones enjoy Disney at 2 years old knowing it won't make it to their long-term memory. It's fine to take a baby to Hawaii even though all he or she will ever really know are the photos from the trip. Not only will you remember, but being flexible and learning to travel become part of who they are, one trip at a time. You don't have to wait for any magical age to take any specific trip. Go when you are ready. And then, go again later if you want them to remember it.

Gadgets and gizmos can help, but people help more

Pop quiz: What's the best travel stroller? Best car seat for travel? Best headphones? Best baby carrier? Best luggage for kids? Best seat extender on a plane?

As a traveling parent in that newborn-to-preschool phase, you'll probably know the answers to many of these things. There's no question the right gear can absolutely make the journey easier. (Seriously, I'll forever be grateful for the Doona.) But don't feel like you need all of the gadgets and gizmos -- focus on the ones that help solve your biggest family-travel pain points.

Oh, and always pack more snacks, diapers and a change of clothes than you think you need in your carry-on. That's actually more important than having the best collapsable stroller.

(Photo by Darren Murph/The Points Guy.)

But what really helps the most when traveling with kids is people. That may be your partner, a stranger who helps load your bags in the overhead bin when your hands are full or a grandparent who you bring along for the journey.

In fact, I highly recommend bringing along a family member whenever possible on trips when the kids are little. We've never regretted a single time that we brought grandparents along for the adventures. You'll all have more fun and make even more memories.

You'll (temporarily) regret traveling at times

On almost every trip we took when my kids were really little, there was often a point when someone said, "We're never leaving the house again." Whether it was massive diaper blowouts at inopportune times, epic sleeplessness in a strange place, puke everywhere or lots of tears (from kids and parents), traveling with kids can sometimes be really tough. Period.

I remember a ski trip to Steamboat, Colorado, when my oldest daughter was about 6 years old and my youngest was around 6 months old, when we literally didn't sleep. At all. The littlest just was an awful sleeper, and putting all of us in a 300-square-foot room meant exhaustion for all. At the time, I thought we were total morons for attempting to leave the house to go to below-freezing weather for exhausting physical activity. But now, years later, I'm glad we did it. That was a big year in which my oldest truly learned to ski, and the bad moments really do get smoothed out in favor of the good memories.

Skiing in Steamboat in 2016. (Summer Hull/The Points Guy.)

We did take take time off from really big or complicated trips when both kids were in those hardest-ages-to-travel phases, but we didn't regret a single trip by the time they were older — no matter how many things went wrong.

Your family will become closer

When all you have is each other, you become closer. My kids are over five years apart, and they don't always just play together at home, since each has her own friends and interests. But when you set out on a journey across the world, it doesn't take long for them to turn to each other for fun and support.

There's no doubt in my mind that my girls' relationships with each other, and with us, are better because of our adventures.

(Photo by Summer Hull/The Points Guy.)

Pay extra for the nonstop, well-timed flight

When it's just you, or just you other adults, it's easy to be tempted by the savings that can come from taking the 6 a.m. flight or connecting somewhere. But when you have little kids, that's a bad idea that you'll regret the first (and likely last) time you do it. Unless you don't have another option, ease is the name of the game when kids are along for the ride.

Avoid unnecessary connections unless you need them for a break in the travel. Rule out predawn departures whenever possible. Schedule the car service, use the Uber, secure the early check-in and do whatever you can to make the trip easier and save your energy for the actual exploring.

Related: How to save money on holiday travel

Suite upgrades are everything with babies and toddlers

Extra living space with little kids is as good as gold. While sleep is a precious commodity with babies and toddlers, you may not always want to go to bed when they do at 8 p.m. or earlier. That's the phase of life when a suite upgrade or maybe even an Airbnb-style accommodation is the most useful.

If you've got the points or hotel elite status to make it happen, splurge on that confirmed suite in those early years. You won't regret it. Having any extra space for the crib for naptime and bedtime is usually worth it.

A Westin junior suite. (Summer Hull/The Points Guy.)

Related: 2-bedroom suites you can book with points

If you can't secure the suite, then consider turning to this baby-friendly travel hack.

Find the parks

When traveling with kids, sometimes you all need a break. Sadly, that doesn't always mean you can actually get a true minute alone to yourself, but you can find familiar territory for all by simply entering a park. Virtually every city in the world has one, and as your kids run toward a swing set or a ball field, you can finally breathe.

While it works for little kids, this tip isn't just for the preschool set. Heading to a green space works wonders for teens and tweens, too. If your kid plays soccer, he or she can play soccer in just about any country with other kids. Same with basketball, or throwing a ball around — you get the idea. Not only can you all just exhale doing normal, familiar things for a bit, but you'll probably be pleasantly surprised at just how well your kids can play with local children even if they don't share a common language.

My first daughter playing with kids in a park in Paris (Summer Hull/The Points Guy.)

It gets easier ... and harder

While reasonable people can debate exactly when the hardest age to travel occurs, it happens somewhere between 9 months and about 3 years. If you are in the middle of that and miss your long-haul adventures of yesteryear, don't despair. I promise you with every mile in my United account, it gets easier. We recently rounded that corner (again) with our 4-year-old, and the big adventures are once again on the schedule. Our 10-year-old is now a full-fledged traveling pro.

(Photo by Summer Hull/The Points Guy.)

But traveling with kids also gets harder in some ways. As we enter the tween phase, there are already groans of "I don't want to be away from friends." And then there are the activities and schoolwork that absolutely get harder to miss as the years tick by. I know enough to know we aren't in the worst of that yet, but it's coming. So, take advantage of the phase of life your kids are in and plan trips accordingly. Some things will get easier, while others get harder. In either case, don't wait around for the perfect time to travel, as all years have something special to offer.

They can do it, and it's worth it

You'll never believe what your kids can do until you give them the chance to do it. My kids both recently snorkeled with sharks and rays in Bora Bora. I was impressed that my eldest got in the water without us, and I was equally impressed that my youngest snorkeled next to me with her little head in the water. That's an experience we weren't ever going to have back home in Texas.

(Photo by Summer Hull/The Points Guy.)

Your baby can adjust to a new time zone. Your 3-year-old can pull their own bag (for a while). Your 5-year-old can walk through an airport after an overnight flight. Your 7-year-old can ski down a mountain. Your 9-year-old can use Google Translate and learn a few words in another language to accomplish a task. Maybe the ages or activities are slightly different from family to family, as not all kids are on the same path, but the point is that your kids (and you) can do far more than you think if you just change the scenery and give yourself the chance.

We've had low points on the road over the last 10 years, but the highs are sweet -- and far more frequent. If I've learned anything over the last 10 years of traveling with kids, it's that it's all worthwhile and you absolutely can do it.

All images by the author unless otherwise noted.