You all know the drill. It’s time for your family vacation and it entails months of planning – weeks of packing (and re-packing) – days of worrying if you forgot to pack something – hours of organizing the car to fit everything in – and just 2 minutes for your kids to complain about something as soon as you’re on your way. This can easily make you question if traveling is worth it at all.
But…here’s the good part. Here’s the secret. Vacations don’t have to be so hard.
For starters, I want you to take that 10-page packing list and excel organizing chart and toss it. Yes, just throw it away (ok, I try to be green, so recycle it, please). If planning a “relaxing” time away for your family begins with weeks of stressed out parents and frustrated kids, it kinda takes away the benefit of vacation, doesn’t it?
I must admit, I tend to be what you would call a “stressful packer”. But my Type A personality stress tends to be focused on the fact that I’ve packed too much. “Why do I have so much in this bag?” “I know I won’t need all this!” “I need to go through it and take more out.” I can usually be found yelling these statements, and more, in frustration to my husband the night before we leave, around midnight, when I should be sleeping. So, I have learned to keep my packing stress to the day or two before our vacation. If I packed for a week, I’d stress for a week.
If imagining packing 24 hours before the flight is causing you to panic, feel free to pack a few days before you leave. I won’t judge.
Also, the more you travel, the quicker you can pack. You know what you need and what you don’t and you may be surprised at how little your kids really need. We forgot all our books on an international vacation a couple years ago. We “read” the same two coloring books to the kids before bedtime, making up new stories to go along with the pictures, and they never even noticed.
As two avid travellers, my husband and I want to keep seeing the world with our kids as they grow. You can check out my blog post 7 Reasons to Travel With Your Kids for more on this. It’s an important part of our life and my goal is to make it as simplified as possible so we can enjoy the planning, packing (ok, maybe not), and the trip itself. After many trips with one baby, then one toddler, then a baby and a toddler, and now two toddlers – I have learned a few things to keep me from pulling my hair out. So, here I am to pass these tips along and make it easier for all of you to travel with your family – and enjoy it!
Before the Trip:
Choose the right vacation destination for your family.
Know yourselves and your kids before you choose a location. Are they active? Do they like to play in the sand for hours? Do they love to ski? Are they history buffs? Do they enjoy exploring new cities or hiking in the mountains? Although my husband and I would love to tour an old European city, we know that this would be exhausting, and possibly boring, for our kids right now. So, although we bring them to Quebec City for the weekend and to Boston for the day, when it comes to any trip over 5 days, we skip the cities and hit the beach for now. We know this gives us the best chance of relaxing and playing together as a family.

Accommodations are key.
This does not mean you need a 5 star hotel. What it does mean is that a two-room hotel with a balcony/patio or a rental house/condo may be well worth the extra cost since we travel with toddlers. There are so many great sites now for renting vacation houses that it can actually be more affordable in the long run. Sites like VRBO, HomeAway, and Airbnb provide you with a place to put the littles to bed and still enjoy the night yourselves. If you’ve ever done the “put the kids down and whisper the rest of the evening in the dark so they don’t wake up” routine, you know how challenging that is. In my mind, that is NOT vacation.
House or condo rentals have kitchens, too which add a huge benefit over a standard hotel room. For starters, you can save money by buying groceries instead of eating out each meal. You can all eat breakfast on your own schedule as you wake up. You can have snacks (and let’s be honest, alcoholic drinks) available when you need them. And you can spend less time sitting at restaurants hoping your kids behave. You’ll also have a kitchen sink (or maybe even washing machine) to wash what you need to!
Learn about where you are going beforehand (with your kids)!
Do some fun research before you go. Our favorite for finding local stores, restaurants, and activities is TripAdvisor, but there are plenty of sites to look through. Have your kids look with you and maybe even pick out a place to have dinner when you arrive. Then dig deeper and learn some of the customs or language if you’re going to a new country. How do they say “hello”? What is the traditional food of the area? Trust me, your kids will feel super cool just knowing how to say “hola”.
Create an interest in planes, trains, and travel.
Little Passports is an amazing way to develop an interest in travel and could make a great Christmas gift for your kids.. I’ve also just introduced my kids to Justin Time on Netflix, a 15-minute cartoon for pre-schoolers about a boy traveling to different countries and back in time, and they love it! When we were in Mexico our son also spent much of the time looking for Dora – never to be found of course – and we had to let him know that she was probably on her own adventure!
The more you teach your kids on a daily basis about these things, the more they’ll look forward to it each time. My son recently woke up at 9 p.m. because he was sure we might miss our train to Boston. He’s been taking it for years and was still too excited to sleep the night before!

Look at the maps before you go and once you get home.
You can even create a “pin” wall map at home. Our son LOVES to put the new pin in when we get home from a trip and asks where we’ll be going next! We had our world map put on foam board and framed at a craft store. Now it’s wall art and a discussion piece for our home.
Give your kids responsibility.
As your kids get old enough, have them choose a backpack and pack their own toys, activity books, snacks, water, etc. Give them guidelines if they are going overboard. For example, let them know they can choose two books, a zip lock bag of toys, one art project, one stuffed animal and three snacks. Have them carry their own bag as long as they can during travel and teach them to be responsible for getting it through security.

PACK LIGHT!
The best thing to remember is that you can usually buy what you forgot or need once you’re at your destination. Unless you’re heading to a third world country, you’ll be able to find a store with diapers, bottles, wipes, sunscreen, clothes, books, toys, snacks, milk (although the milk may come in a small warm box on the shelf…yes, this is normal) and more. Trying to cart multiple suitcases, strollers, backpacks, and kids through the airport is miserable. The less you have to haul around, the better for everyone. Plus, let’s be honest, you know you’ll end up bringing stuff home – so leave room! I’ve even contemplated not packing any toiletries at all and just buying sample ones when I get there (if anyone has done this, let me know if its worth it).

Travel Day
Have “day of” gear ready.
To reduce stress the morning of your vacation, I always place the travel clothes and shoes out for each family member and have my kids each pack their “travel bag” the day before, too. These should be ready to grab and go as you walk out the door.

Charge the electronics!
Yes, you may need the Kindle, iPad, iPhone, or whatever distraction you have for a long flight or car ride. Maybe add a new game or two so they are intrigued for longer than usual as well.
Meet the Pilot or Flight Attendants.
This is a sure way to have your kids enjoy the plane ride. Even just shaking the pilot’s hand or saying “hi” is huge for a young child. Introduce them to the flight attendants too, since they’ll be interacting with your kids during the flight.
Wear the baby as long as you can.
For me, the little one would go in the Ergobaby as soon as we were about to board. I’d take them off to nurse during take off. Then one of us would put them back on and walk up and down the aisle of the plane until they fell asleep. This can buy you an hour or so – heaven when you’re on a plane!
Expect the worst.
Prep yourself for airline delays, crying kids, tired parents, and poopy mid-flight diapers. They will happen. Take a breath and just know that someday your kids will be easier travelers (and you’ll long for the days you could fly with them on your lap).
Bring a stroller and gate check it.
A long layover with a tired kid can ruin a trip if you’re trying to carry them and your bags. We always put our stroller in one of these stroller bags just in case it loses a wheel or part in baggage. When flying alone with the kids, check your bags and just bring one backpack on the plane. You’ll need both your hands and as much seat space as you can get.
Candy, snacks, juice, and did I mention…candy? Need I say more?
Stay Relaxed.
This is a hard one, and one I’m still working on to be honest. But at least my husband and I stress about different things – so there’s some balance right? I stress when I’m jamming too many clothes in the suitcase while he tells me it’s no big deal (thankfully). He stresses when we’re not sitting at the airport gate an hour before the flight while I remind him we have plenty of time. But the key is once we are off the ground, we all relax, sit back, and enjoy the ride.
Overall, planning and traveling can be easy, and even fun, once you get a simplified routine in place. So, when your next family vacation comes up notice what things are causing you stress, vow to stop doing them, and enjoy.
I’d love to hear what your tips are for stress-free planning, packing, and vacationing with your family! Feel free to share!