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Challenge: Traveling with Kids

Travel With Kids: The 6 Keys to Keeping Your Sanity

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For the 2014-15 school year, my husband, Kyle, and I took our three kids on a round-the-world trip (affectionately called our Big Trip). They were 9, 6, and 4 when we started, and were 10, 7, and almost 5 when we arrived back on U.S. soil nine months later. We traveled westward, starting in China and ending in England, hitting four continents and 28 countries in between.

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We lived off our ongoing online work, money we’d slowly saved the previous five years, and a lot of dogged frugality. The kids were “worldschooled” that year, mostly using digital tools and the ground we walked as their textbooks.
It was hard. It was tiring. And we loved it so much, we hope to do it again one more time before our oldest leaves the nest.
I’m very much a normal person. I’m not a glutton for punishment who loves the thrill of screaming toddlers on airplanes, nor do I fancy myself a base-jumping, fly-by-the-seat-of-my-pants kind of Fun Mom.
My family lives off a run-of-the-mill salary from my work as a writer and entrepreneur, and most of the time, the floorboards of our car are an absolute wreck. My kids often whine on long road trips, they clamor for screen time far more than I like, and many times, I’m frustrated by their lack of astonishment when we take them somewhere astonishing.
But, I still love to travel with my kids. My homebody self loves to wander back roads with them. I believe the hullabaloo is worth it.
It takes strategy to make travel with kids a thing to be savored and not a death wish. But if you’ve got an unquenchable desire to explore more of the world, don’t let your kids stop you. Bring ‘em along.
Here are six keys I’ve learned that make traveling with kids a delight.
1. Let go of expectations.

This is the first key to actually enjoying travel with children. No ingenious travel hack, no nifty piece of travel gear from Kickstarter. The first key is to toss that Instagram-perfect roadtrip out of your head, and enter reality.
I don’t even mean lowering your bar way, way down. I mean tossing out your original bar and getting a whole different one.

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This isn’t meant as a bummer. This is simply the foundational mindshift you need before you even begin to plan that trip with your kids.
When we first moved overseas, I heard a phrase that became my curmudgeonly motto during our years there: Expect the worst; hope for the best.
This is my motto for traveling with my kids.
Life is different while you’re traveling. I’d go so far as to say we become different people when we travel. To prepare for a trip as though we can control it will only set us up for crushed expectations.
Hoping for the best but expecting the worst works for all of us, traveling all the time. But it’s especially helpful as parents traveling with our kids. This is the number one foundational key to an enjoyable adventure exploring the world as a family.
2. Practice.

If your dream is to one day take your kids to London, rent a flat, and use public transport to get around both the city and to venture beyond on day trips to small villages, plan a family vacation to a nearby city first.
Plan a weekend away in Chicago, for example, book a guesthouse on Airbnb or HomeAway in the city, and use Google’s Transit Maps to plan your time relying on the Chicago Transit Authority. Enjoy the city sites, but for one of your days there, head to a beach town, like St. Joseph, or another city, like Milwaukee, to practice using public transportation.

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If you’d love to one day hit up all the national parks in the United States via travel trailer, first rent a trailer and spend a week at just one of the parks, or even a nearby state park.
Practice makes for great travelers.
Give your kids the chance to become good travelers. The more you do it, even on small day trips, the more adept they’ll be to life on the road.
3. Make it affordable.

Don’t wait to travel until everything meets your ideal dreams—there’s lots of great travel experiences to be had on the cheap.
Here’s a few ways we curb our travel expenses:
  • Rent apartments or houses instead of staying at hotels.
We’re big fans of services like Airbnb or HomeAway, where we can rent places in real neighborhoods from locals. This is our go-to method of housing for any trip longer than two days, and these places become a memorable part of the experience, and they’re usually cheaper than standard hotels.
  • Cook for yourself and eat like the locals.
If you stay at a guesthouse, you’ll probably have a kitchen—which means you can cook for yourself. This is part of the experience as well, especially if you pick up local groceries from a nearby market. We like to cook dinner and breakfast at home, saving our meals out for lunch.

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  • Sprint through more expensive spots and linger in the cheaper places.
There’s a reason we spent almost two months in Thailand—it’s cheap there. We explored Hong Kong and Singapore, but we sprinted through those higher-priced spots and then slowed down in nearby Thailand. (This is good for both your wallet and your sanity.)
  • Avoid group or guided tours—stick to self tours.
Instead of hiring a tour guide at a famous landmark, these places often have free or cheap apps with guides that are just as enjoyable (or you can rent handheld devices). Or, just skip the tour all together and enjoy simply being there. Ask someone who looks like a local if you have any questions, watch YouTube videos in advance to give you an advanced screening, and read books afterward if you want to explore more.
  • Spend more time just being instead of exploring all the tourist activities.
A few occasions warrant doing the tourist thing, but you’ll get more out of your experience if you enjoy off-the-beaten track stuff—and it’ll save you a ton of money. Visit the Eiffel Tower, sure, but then wander the market on nearby Rue de Cler, pick up some fantastic, new-to-you cheese and bread, and have the best picnic of your life somewhere in Paris’ green spaces.
  • Travel off-season.
Summers on Martha’s Vineyard and winters in Breckenridge will always be more expensive because they’re in the high season. Travel during the shoulder and low seasons, even with kids and their school schedules, and you’ll have a more enjoyable, and definitely more affordable experience.
The crowds are so much smaller, housing and flights are light years cheaper, and you might find some hidden gems for a steal that would otherwise be unavailable when vendors have tons of tourists to charge full price.
4. Incorporate real life.

....while still making room for occasional treats.

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There’s a benefit beyond money to traveling slow and off the beaten path: you’ll have sweeter family memories.
Traveling fast and cramming in everything in the name of Seeing All The Things makes for stressed out parents and kids. And stressed-out travel is no fun.
Sure, there are days here and there that require hustle, but most of the time, your travels will be the stuff of sweet childhood memories when you move about the cabin slower, savoring life.
This looks like living and eating like the locals. It looks like sleeping in. It looks like tossing out your usual rules in the name of experience—let your kids order a juice or soda on the plane, let them watch movies from here to Nairobi (let’s face it—you want to do that, too), let them stay up late to enjoy that famous Spanish late night culture.
This might look like worldschooling or roadschooling, especially if you want the freedom to travel unencumbered by a rigid school year. It sounds daunting, but it’s more doable than you think.
5. Pack simply.

I’ve found that it’s almost always more of a headache than a help to overpack. It’s good to bring what you need, of course, so there’s no need to pack like a monk in the name of trendy minimalism—but there’s really no need to pack something just in case.

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Most of the time, there is no ‘just in case.’ You’ll be better equipped to enjoy the moment, be all there, and explore your surroundings.
Kids don’t need many toys, and when they’re stuck without them, they usually make whatever’s around them their plaything (hello, sticks and rocks).
6. Debrief well.

Returning from a trip is just as important as being on the trip. Re-entry can be bumpy, especially when your travels were truly enjoyable and real life beckons around the corner.
Before coming back to the world of housework, school, and regular routines, I like to debrief the family. This isn’t anything fancy; it mostly involves asking open-ended questions and us sharing our answers. It’s done casually, over some of our last meals, on the drive home, or as we’re walking around.
The kids are barely aware we do this. But it invites them to a place where their thoughts, impressions, and emotions about their experience matter, and it tells them that whatever they’re feeling is valid and heard.

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How early we start the debriefing process before returning depends on how long our trip was—if we went away for the weekend, we start talking about real life only about an hour before pulling into the driveway. When we’re gone for nine months? We start debriefing about two weeks before our final flight.
We ask questions like:
  • What were the highest points of my travels?
  • What were the lowest points?
  • What stories can I share with close family and friends?
  • Did anything disappoint me about myself?
  • What pleasantly surprised me about myself?
  • What surprised me about certain cultures?
  • What were my favorite countries/cities? Why?
  • What were my least favorite countries/cities? Why?
Traveling with kids can be a tiring endeavor, but here’s what’s been most surprising to me: it’s changed me for the better, as both a parent and as a human.
Witnessing my kids delight in the world, explore new surroundings, adapt to uncertainty, and soak in the here-and-now has taught me how to better slow down and savor the small things in life.

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Traveling with kids gives me the gift of appreciating being at home with them anywhere, knowing it won’t last forever. When the time comes for them to stretch their wings and explore the world without me by their side, I can rest easy that they’ve had lots of experience with me as a witness.It’s been worth every headache, every hassle, and every chaotic adventure.

Experience our year of living out of backpacks traveling the world—without the cost of a plane ticket—in Tsh's new memoir, At Home in the World: Reflections on Belonging While Wandering the Globe (Thomas Nelson, publishers).

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