Vacationing With Kids

How many people have been told that traveling with kids is a nightmare and that you won’t be able to do it once you have a baby?

As someone who did a lot of traveling in my pre-baby days, I was told this on countless occasions. Then, I had a baby and got to experience this first hand and let me tell you, it really isn’t that bad… depending on how many kids you have I suppose. A better way to put this is “it could be worse”.

It definitely isn’t as easy as traveling childfree with your partner but you really just need to weigh your options here and decide if you are willing to try it because you want to sit on a beach somewhere tropical or if you are going to avoid it because you don’t want to deal with a child in a steel tube with nowhere to go for multiple hours at a time.  A good ol’ vacation cost benefit analysis, if you will. I have gone through some tips and tricks we have learnt along the way (much more of a knowledgable post than my previous more aggressive ones). This may be helpful for some of you who haven’t done much traveling with young kids but also may not provide any help to others who travel lots.

Challenge 1: Navigating the airport with a child

I feel like this is where I should add that packing light makes a HUGE difference but also know that I don’t even take my own advice when I say that (see top photo). I guess I like making things more challenging for myself…

Anyway, after checking in for your flight and weighing/dropping your 17 bags off (the start of a very sweaty day), you get a bit more excited before remembering that you still have to go through security and customs (if traveling outside of Canada) with your children and the 6 carry-ons you’ve brought along.

PRO TIP: You are allowed an extra carry on for your child (such as a diaper bag) but I would try your hardest to not have a ton of carry-ons as you will be juggling your child and potentially a stroller/car seat already. You are also allowed to check two baby items for free but definitely look into that depending on what airline you fly with as I have found that they suddenly change the rules. Last time we flew to Palm Springs, everything was fine on the flight out and we checked in two baby items per kid for free but coming back from the States, the people at the airport said that the free items can only be car seats and not pack n plays. Needless to say, they “let us go ahead” free of charge but I’m still confused how it can be different depending on what airport you’re at.

Next, as you arrive to security and see the giant line ahead, just remember that having kids means you get to cut the line. So, when you get there, just confidently cruise on through toward Nexus and they will pop you into a fast lane to speed things up because no one in there wants to hear or deal with your loud kids.

If you have a stroller, be prepared to evacuate the sleeping baby and everything else that’s in the stroller or car seat as they need to scan this all separately. This is extra annoying if you have a sleeping infant and you will later find out that it gets more annoying as you carry on to customs. Don’t bother strapping your child back into the stroller after security because that baby has to come out again in about 10 minutes.

If you’re traveling with an infant or younger child who still eats purees, squeezy packs, formula or breast milk, this is where you are hopefully very organized and can take all these things out of the same bag and pop them into a bin for security agents to test. In case you didn’t know, having little ones also means that you can bring all sorts of usually “not allowed” items through. All items I listed above are AOK (at least from Canada to US and back). They just need to test them quickly after sending them through the scanner.

Wanting to bring breastmilk through the airport? Not a problem. Just takes some extra planning…

I learnt this from a friend when I had my first child and was traveling for work at 4 months postpartum and it really helped me. If you have breastmilk baggies or bottles that need to stay frozen, you bring a small cooler bag, fill it with ice (and your breastmilk baggies) and then dump it before security. Then, once you get through security, you go to the first coffee shop or restaurant you can find and ask for more ice for your cooler bag and voila! You should be good to go for the next several hours, unless you’re traveling overseas, then maybe rethink that plan.

I like to pack pre-made bottles of formula or breastmilk, a bottle of water in case I need to make more and squeeze packs for a quick snack if needed. Again, it’s kind of weird that you can’t bring water through when traveling as adults but you can with kids. I guess they don’t want to deal with thirsty screaming children!

Next up, you head to customs! Almost there!

This is where you realize just how annoying it can be if traveling with a sleeping infant.

You know how those little machines have to take your photo and check your passport? Well, they also have to take your baby’s photo, meaning that you have to hold/dangle your baby or babies in front of the bright ass lights (i.e waking her/him up) and take their photo. For some, this will be extra annoying if your baby just fell back asleep after security.

If you have toddlers, this is where shit can go sideways. You need to focus on getting your passports scanned and answering all the skill testing questions on the machine so that you aren’t flagged while your toddler may suddenly realize how big the room is and may want to do some kick ass dance moves or just some hard sprints in every direction. Here’s hoping you have someone else with you to wrangle him/her in. Or maybe a leash? Are those frowned upon yet?

Once you get through security, it becomes a free-for-all and you have to somewhat realize that you are now in full on survival mode. Just keep everyone happy before boarding. I usually find a spot to park everyone down, get some food (most likely nothing nutritious for the toddler), maybe a couple glasses of wine for mom and dad and just let the kid run around while I brainstorm how to board the plane with all the bags, stroller, kids, etc.

Challenge 2: Boarding the plane and flying with a child

Be prepared to be sweaty no matter how many kids you have. Pre-boarding is a real win here as it gives you extra time with your stroller, 800 bags and the kids. Our tactic usually involves Sylvain taking a couple kids (or my parents if we have them with us) and then I take the other one while staying back to pack up the stroller and car seats into one of those big red bags. Here comes phase two of the sweat. Once I get the stroller in the bag, I board the plane (woo!) and again, things may take a turn depending on how long it takes to get everyone on board.

The toddler is big into television these days so that’s usually an easy fix but now we have two infants and to be honest, the most recent vacation we had, we also had my parents there for extra hands, making this much easier so I will generalize a bit here and say that there is one key item I suggest bringing when flying with infants under the age of 9 months or so. A breast-feeding pillow like the one shown below. It’s small, comfy and doesn’t bother anyone sitting next to you. This saved me when traveling with our first-born multiple times when she was little and has come back as a real winner with the twins. The reason being that it allows you to be hands free to enjoy a cocktail, play on your phone or just not have a numb arm from holding a baby non-stop. It also plays a solid role once arriving to your destination as you can use it as a cushion for them, breastfeeding, or a jumbo neck pillow for you if you really want.vacay2


Other items that are helpful for toddlers and infants on the airplane:

  • Ipad stocked with lots of Netflix shows already downloaded
  • Lots of snacks for the toddler (and babies)
  • Toys: old and new (a friend of mine taught me to wrap several new small toys up and as soon as the toddler gets a bit fussy, you bust one of them out like its Christmas and BAM, toddler is happy again…or at least for another 10 minutes
  • Change of clothes for all kids involved. Blowouts on the airplane are not a happy scene. Picture me trying to use the airplane sink in the washroom to clean a large blowout when it turns on for like 2 seconds and then switches off. Not ideal
  • Dry bag or any sort of plastic bag in case of said blow out or dirty clothes
  • Swaddle blankets (they are small and work for everything)
  • Bottle of formula or breastmilk for infants to drink while taking off/landing (or the boob and/or soother works too)

I’m not going to lie, we haven’t always had the smoothest flights since having kids but you tend to forget about just how bad it was and it usually feels worse for you than for other passengers… I think. Yes, there will be occasional tantrums, tears, definite screaming, non-sleeping kids when they should be sleeping, whines (both types – toddler whining with a side of pinot), and a very messy floor underneath you but if you go into it knowing it’s going to suck, it seems to make it a bit better… at least for us! We even have a toddler who could literally watch TV all day long at home and then she gets on the plane and decides “nope, today doesn’t seem like a great day for tv, I think I want to go for a jog instead” … that was super cool.

Again, I am talking mainly about shorter flights as opposed to long-haul flights as I can only imagine that would be a disaster with three young kids (we did Europe with Sawyer when she was two months and it was totally fine but it was only one child and she was basically a blob). It all depends on the timing of your flight, the ages of the kids and whether or not you REALLY want to deal with the extra work to get somewhere awesome or not. You don’t really know until you try it! And if you try it and it was horrible, you can decide to wait several years before going again! 😉

TWIN PARENT TIP: If you fly with your partner and the twins and haven’t bought an extra seat for the babies, you and your partner will have to sit across the aisle from each other and both hold one baby (definitely book seats ahead). This is because in a regular row of three seats on the plane, there are only four oxygen masks so if you and your partner were to sit in a row of three with one extra kid or random stranger in the third seat and the twins on your laps, you wouldn’t have enough oxygen masks for everyone.

Challenge 3: We made it and now the vacation can start…sort of

This is where a big part of the vacation analysis happens for me and again, totally depends on how many kids you have and their ages.

Naps play a huge roll here. They can really bind you to your house, condo, hotel, etc. For example, we now have three kids. Two of those children are on 2-3 naps a day that usually happen around 9am, 12pm, and 3pm (these are rough times as we are not super scheduled). The babies may nap for a minimum of 45 minutes and up to two hours. We also have a toddler who takes one nap a day around 1:30pm for one to three hours.

This means that we tend to always have at least one child sleeping between the hours of 9am and 4pm and either me or my husband has to be in the rental property during those times.


Again, we enjoy vacationing so it’s still worth it for us depending on what sort of accommodation we rent. If it’s a house with a pool, we are good to go because at least we can swim or sit in the sun while the kids sleep. If it’s a condo with a shady deck, this isn’t as fun for us due to nap jail but it works depending on proximity to the pool or beach. If it’s a ground floor condo with a sunny grass patch outside, this is still somewhat ok as we can sit outside in the sun but would then get rather sweaty and not be able to get to a water source because… nap jail. I hear cold showers are cool on vacation though.

Obviously, we have also napped our infants in the car seat, on lawn chairs by the pool or on a towel at the beach but as most parents know, this only works up until a certain age and I feel like 5 months was the cap for us being able to do the lawn chair naps. We could also try and just wing it and skip naps here and there but I can assure you that our toddler would be a gong show after a few days and I think it would steer us away from vacationing with her ever again.

I just realized that this section of the post may as well have been titled “Nap hell on vacation” as that is really the main part of our analysis these days, but I think if you have multiple children who nap, you are probably in the same boat. Or maybe not because yours are all on the same program.

This brings us to the next part of the analysis: Accommodation and Accessibility.  A big one for us these days is realizing that we need at least two bedrooms (or a giant one bedroom with a big enough closet for the toddler) and somewhere close to a water source (pool or ocean). I should have mentioned that we typically stick with sunny vacations so that’s what I’m going with here.

We like to be somewhere that enables us to walk to the pool or ocean easily or at least pack up the car. However, packing up 3 kids every day with a full cooler and all the gear on vacation sounds somewhat painful.


Is it worth the airport madness with all 3 kids, the long travel day (even if the flight is short), the airplane ride where we may have 3 kids freaking out simultaneously, the excessive sweat dripping down my body from this long travel day?

Is it worth the large amount of money to stay in a larger unit, hopefully on the water, with all three children and deal with the possibility of being stuck hanging around the condo all day?

I have drawn a very detailed image for my analysis that I think you will all find rather insightful, while extremely helpful with your future vacation hesitations . I know, you don’t have to tell me that I should’ve been an artist back when I chose my profession. It’s so obvious how gifted I truly am.


This very detailed drawing has helped us decide what is worthwhile for our future vacations. We are currently looking to book a vacation in the Spring so I would say it’s a yes for us and will update you all on how that went once we return. We’ll either come back saying it wasn’t too bad and it all worked out or else we may decide to ship the kids back home. Stay tuned!