Creative Child

Traveling with Children

by Michelle Dempsey M.S., CPRW

Ah, vacation. Time to unwind, disconnect, and let your brain escape the realities of every day life. No worries, no stress, no schedules or plans.

Unless you’re traveling with children.


Don’t get me wrong. Traveling with children is every bit as great as traveling was before you became a parent – if, and only if, you go into battle fully prepared. Knowledge is power, as they say – and you definitely want to put in the research and brain power ahead of planning your next family vacation to ensure things run as smoothly as possible.

Part of the benefit of a family vacation is to give your child an experience they’ll never forget. The other part is being able to take in their happiness and excitement as if it were your own, and feeling really great about the fact that you were able to create these memories for your family. One great piece of advice I was given when taking my baby on her first trip was, “She’ll never remember if you forgot her favorite toy or extra snacks for the car, but she’ll look back at pictures and feel so special to have made these memories with you.”

Thinking back this trip with our daughter, a mere 6 months old at the time, makes me realize how unprepared I was for our first ever out of the house, overnight experience with baby.


One year later, however, I am a bit more broken-in, have put in the exhausting leg-work, and have traveling with toddler down to a science – the main point here? Go big or stay home.

4. Plan ahead – big time.

The most foolproof way to ensure a great getaway is to do your research.

Putting in the time – ahead of time – to ensure you are choosing a child-friendly vacation spot with plenty of entertaining options for the kids will save you a lot of trouble in the long run. An example? Pass up the great deal on that five-star hotel with only one fancy French restaurant on the premises. Unless, of course, your children fancy escargot.

I can tell you this – I’d rather spend my evenings eating macaroni and cheese next to a happy child rather than begging a restaurant server to create a child-friendly option for my already picky eater, and then having to wrangle down a hungry child to bed in a foreign place.

3. Pack heavy.

I have always been an over-packer. I have been known to pack twelve swim suits for a 5-day trip, and have never returned home from a vacation having worn everything in my suitcase. Call me crazy, but I think it’s best to be over-prepared than the opposite. The same absolutely goes for traveling with your little ones.

My rule here? If you think you need it – if you think for even one-second that this object might make your child happier/more comfortable/easily entertained – it’s worth the extra weight in your suitcase.

2. Travel heavy.

Yes, the trek through the airport will be a bit inconvenient and uncomfortable. Sure, your neck will ache under the weight of your overstuffed carry-on bag, and your car will take hours to clean out following your arrival back home. But the kiss of death on any excursion is not coming prepared with enough whoozamawhatsit’s to entertain your kids on board a long flight or in the backseat of a cramped car.

The adventure to and from your vacation destination is the perfect place to break out the iPad, the snacks you’d normally say “no” to, and a slew of engaging toys and books. Think of the three F’s for smooth sailing – food, fun, frills. Kids love these, and your fellow passengers will, too!

1. Don’t forget your sense of humor.

The sooner you accept that traveling with children is like wearing white gloves to a ketchup party, the better off you’ll be. Just like with parenting, traveling with children means you are responsible for another life, no matter how much fun you’d like to have, no matter how much work it takes, no matter how easy traveling once used to be for you.

With every other part of your life since childbirth, you know that everything is different now – a better kind of different, sure, but different nonetheless. Traveling is no exception – but if you adopt the right attitude, learn to laugh at the mistakes you’ll make along the way, think of each challenge as a learning experience, and remember that you’re doing all of this for the best of your children – you’ll have the best trip of your life.

Now get packing!

A writer, entrepreneur, radio host, and powerful motivational speaker – Michelle Dempsey, owner and founder of Michelle Dempsey, Very Well-Written, has one goal in mind: empowering women from all walks of life with her incredible personal life story of overcoming adversity and using the lessons learned to achieve success. Internationally published and known for her ability to connect with readers on a deeper level, Michelle has successfully united her passion for business and writing and developed a thriving career, offering writing and editing services, business coaching, branding expertise, and content marketing to business of all kinds.

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