Ways to Make Vacationing with Kids Easy

Someone once told me that family “vacations” with kids were a myth – like unicorns or toddlers that don’t throw tantrums.

Apparently “vacation” implies a fun and relaxing getaway. When you travel with kids it’s simply called a family “trip”.

I wholeheartedly disagree.

You can absolutely have a fun-filled vacation with your whole family, kids and all.  Let me show you how. 

This is the final installment of “The Ultimate Guide to Traveling with Kids” series (Part 5 of 5!).  Reading each step is critical to your family vacation success!

If you’ve missed the others, here is what we’ve covered so far:

Part 1 |  A Mom’s Guide to the Pros/Cons of Trains, Planes, and Automobiles
Part 2 | 
5 Easy Strategies to Plan the Perfect Trips with Your Kids

Part 3 |  Essential Packing Tips for Family Vacations
Part 4 |  Surviving a Road Trip with Toddlers

And no matter what stage of planning you’re in, be sure to check out my travel checklist.  This freebie gives you a great checklist for planning, preparation, and packing.

Without further ado – here’s how to make vacationing with your kids easy and enjoyable.

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Realize That Kids are Both Excited and Scared of Travel

Take a second to imagine how you feel on vacations.

Sure, you’re happy and excited… but aren’t you a little anxious too?

It’s fun getting to see new things, especially things you’ve been thinking about for weeks or even months.  But you’re also living out of a suitcase,  in an unfamiliar space, and surrounded by new experiences.

Understanding how your kids are feeling will help you interact with them appropriately.  Since you’re not at home, you can’t have the same expectations of them.

They might be more shy, a little less forgiving, or a lot more clingy.  Expect it and respond accordingly.

One way we help our children feel comfortable during vacations is to wear them (usually on our backs because toddlers can be heavy).  In my opinion, there is no carrier in existence better than the Kinderpack.  

Toddler Vacation Travel Kindpack


Look at me rocking that thing with my almost-40-lb toddler in Ireland!  There are a million reasons why I love them – starting with the fact that it’s a family business and all their products are made in the USA. 

They come in four sizes (Infant, Standard, Toddler, and Preschool) and their designs are cuter than you can ever imagine.  Browse through their shop and you will have a very difficult time choosing which one you love the most.  Mine has is full of chemistry and math equations… because I’m a nerd. 

Kinderpacks are insanely comfortable, both for you and baby.  It allows the weight to rest mostly on your hips, rather than your back.  You also have the choice of wearing them on your front or back.  Lastly, be sure to get one with the Koolnit because it breathes better. 

Ok but you’re probably asking – why is she even talking about child-wearing?

Remember that YOU are your child’s rock when you travel.  YOU are one of the only familiar things to them.  Because of this fact, it’s YOU they want to me close to. 

Child-wearing allows them to experience the vacation being comfortable and close to you.  After they familiarize themselves with a new space, they’ll ask to get out and you can let them explore on their own.

Not to mention, child-wearing allows them to take a quick power nap if the situations arises.  This brings me to my next point…


Throw Their Schedule Out the Window

When you’ve put kids in a different environment, you can’t expect them to adhere to their usual schedule.  It’s important to accept that now.

Sure, they’ll still be tired and need to nap… but expect it will be on their terms.  Not that perfectly dedicated 2 hour gap you planned perfectly in the middle of the day.

But don’t fear – this change is so good for kids.  Being flexible is a great skill to learn starting at a young age.  It will make them easier going and more adaptable in the future.

Now this is all easier said that done – how can you possibly ignore the schedule you’ve been adhering to for years?

For starters, listen to your child.  Not just what they say but also to their behavior.  They’ll let you know when they’re hungry, tired, overstimulated, etc.

You’ve also got to be equipped to handle any situation.  We always have a stroller with us when we travel – and it’s not one of those cheap umbrella ones.  You want to bring a stroller similar to the City Mini Stroller.

Best features of one like this is the fact that it has big wheels (so it goes easily over bumpy sidewalks and/or trails) and is very smooth to push. 

Most importantly, it can lay completely flat!  Great spot for naps and diaper changes.  Plus the cover actually does a very decent job of blocking sunlight. Everything I need for emergency situations is stored in the basket underneath.

And yes, I only bring a single stroller (even though I have 2 kids).  Mainly because double strollers are HUGE and difficult to transport.  Also because in a pinch I can squeeze them both in a big enough single (like the city mini). 

Another good tip is to always make sure you are armed with plenty of snacks in case someone is unexpectedly hungry.  For me I’m always stocked with lots of toddler food pouches and quinoa puffs.  And don’t forget a good water bottle!

Related Post |  Surviving a Road Trip with Toddlers
Related Post |  Essential Packing Tips for Family Vacations

toddler travel airplane road trip planning

Location, Location, Location

Where you stay and how you get around has a HUGE impact on the success of your vacation.

Try to stay as close to attractions as possible, preferably within walking distance.  At the very least try to stay near some form of public transportation (subway, bus, etc.)

Kids get grumpy and drained in cars – so if you have to drive everywhere expect they’ll be more difficult when you arrive at your destination. 

On the other hand, kids LOVE riding public transportation – it’s an attraction in and of itself!  Just look at how happy Ry is riding the streetcar in New Orleans:


Walking is fun too – they get to drink in the essence of the city you’re staying in and see everything up close.  You’ll be amazed at the details they notice and how much more about the city they will remember after you family vacation comes to and end. 

If your destination isn’t one that’s walkable or doesn’t have public transportation available, a rental car is an absolute MUST. 

The car can be your staging area – keep in stocked with coats, bathing suits/towels, snacks, busy activities, the stroller, etc.  Also having a rental car allows you to conveniently keep the car seats installed. 

If you have to rely on taxis all the time, you’ll be super rushed trying to install car seats.  And you know what you get when that happens?  This:


This was in Amsterdam.  We had to take a taxi to the airport at 5 am and we were so rushed that my poor husband didn’t install the car seat correctly… halfway through the trip poor Ry was on his back.  Whoops.

Do yourself a favor and stay near public transportation OR invest in a rental car – it will make your life so much easier.

Related Post |  Baby Sleeping Essentials
Related Post |  Answering the Tough Questions About Car Seats on Airplanes



Provide a Place for them to Recharge

Even on a family vacation – kids need to have a home base. 

Of course this can be your hotel room, but if possible I like to stay at an Airbnb to give everyone a little more space.

To make it feel a little more familiar, be sure to bring personal items from your child’s bedroom.  I bring their pillows, blankets, stuffed animals, and toys. 


The very first thing we do when we get into our room is create their sleeping space.  I let them choose where they want their cots set up, which side they want their pillow on, etc.

Instantly kids feel more comfortable being provided with something familiar.  They often like to sit there for a while reading or playing before they venture out and explore the rest of the house. 

toddler busy activities travel road trip


Plan Flexible Activities

Don’t plan too many family activities in a day… but don’t have a completely empty schedule either.

A good rule of thumb is to plan one “definite” activity for the day – like an aquarium, pool visit, or show – and have a few possible activities for other times.

For example, you may be definitely planning on going to a rodeo show when you’re in Denver.  If the kids are feeling up to it, you might also take a train ride.  If their mood is iffy and you don’t want to be stuck on a train with your kids, the backup plan could be a quick hike in the park.  

When scheduling outings, make sure you’re planning a mixture of activities for every family member.  It’s your vacation too!  It’s not just about the kids.

When we were in Dublin, we hit up the Guinness Factory for a tour and quick taste.  The kids had a blast checking out the museum!  Don’t be discouraged from doing things you want to do – even if they’re not directly targeted for kids.


I also highly recommend locating the nearest playground.  That’s a great impromptu activity and way to let the kids burn up some extra energy. 


On a similar note, plan a variety of restaurant options – both for dine-in and carry-out.  There are times you’ll need to sit down and relax but also times you’ll just want to grab food and get home. 

Travel vacation kids fun


Remember to Breathe and Smile

Most importantly, remember to breeeathe.

Try to relax and let things go on vacation.  Being stressed isn’t going to make you have more fun.  If they have ice cream for dinner, it’s not the end of the world. 

Make sure you are present.  Resist the temptation to check your text messages and work e-mail every 5 minutes.  Pay attention to your partner, your kids, and yourself. 

Be appreciative of the chance to connect with your family and the opportunity to discover a new place.  And remember to smile. 

Finally, take lots of pictures – of both the good and the bad times. 

I took this picture around 2:30 am after I was awake all night with my toddler who had thrown up all over her crib.  It was terrible – but looking back on it now I think it’s such a sweet picture.

Pictures help us to remember our travels and they are mementos the whole family will cherish forever. 

And that’s a wrap!  I’ve walked you through all the steps to ensure you have a fantastic vacation with your kids from start to finish.  From the early planning stages to the packing and through the traveling itself

Now go out there and explore!  Make memories!  And be sure to remember to pack plenty of busy toys!

About Author


Hi, I’m Jo!

I have two small children, Ry and Lily, only 19 months apart. It’s usually crazy around my house, but thankfully my wonderful husband is around a ton and helps keep the peace.

I also own my own business and work full-time. I’d love to list all these amazing hobbies I have, but honestly I can barely handle keeping the kids entertained, the house clean, and food on the table. Although on days I’m too tired to do housework, I love to pour a glass of wine and watch Supernatural or Murdoch Mysteries on Netflix.

My husband and I like to stay very busy and drag our kids everywhere with us. Weekends often include relaxing at wineries, festivals, exploring Washington D.C. and other short getaway trips.

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