Traveling With Little Ones Part II

Traveling with little ones is no easy feat, so taking all three of them on a plane to Jamaica for five days was going to be the biggest challenge yet.  Granted, we did bring another person with us to help with the kids, but it still took a lot of planning and coordination to pack, prepare and execute. For anyone who might be traveling via plane to a vacation destination with toddlers or babies, I figured I would share some tips and products that made the trip a bit easier.

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Some ask if we enjoyed the vacation and in the simplest terms, yes. Our definition of an “enjoyable vacation” is different now that we have kids.  It’s less about napping under the palm trees, sipping rum punch and dancing the night away at a beach party. There was none of that. Most of the joy comes from how our children experienced the trip. When they’re happy, we’re happy right? It’s seeing them try new things, explore a new place and have as minimal meltdowns as possible. A big part of this is recreating some of their routines and creature comforts away from home.


I am proud to say I was able to pack all five of our clothes and necessities into 2 suitcases, a duffel and two carry-ons. And you have babies or toddlers, you know how much stuff they require to function, including wipes and diapers. I packed all the diapers and pull-ups that we would need for the entire trip because in Jamaica, I wasn’t sure what would diapers were available, how accessible they were off-resort, and that they would be incredibly expensive.

Packing cubes/compression bags

If you know me well, you know that I’m a lover of compression bags for packing and storing clothes…no vacuum needed! Just stuff it, roll and pack! It really came in handy for the kids clothes and diapers.

Here are the ones I love using:

Clear cosmetic bags

I use these not just for cosmetics, but for everything! There are so many little items to pack with kids, so these bags make it easy to organize everything and see exactly which bag it is in. Especially for carryons, when you need to pull out things on the fly while in transit, or just to make going through security with formula and snacks a breeze, these are clutch. I found mine at Marshalls, but these on amazon seem just as good!

Reusable silicone storage bags

I use these silicone bags at home for everyday snacks since it reduces our single-use plastic and is a healthier choice for food storage. I brought them along the trip to serve the same snack-carrying purpose. Whenever we’d go to the buffet hall, I’d stuff some cereal or other snacks to take along with us throughout the day, and it was easy to wash out and dry as well.


It was going to be the first flight for Chase and Camden, and Chase was having a LOT of anxiety about flying. We did a lot of prep ahead of time for him, talking about flying, showing him videos/books and also taking him on a dry-run to the airport so he could see that planes. After an initial mini-meltdown as we were getting on the plane (he wanted to go back and stay in the airport), he was fine once we settled into our row. Some things that made it easier to adjust: we got him a tiny new toy car that he would be able to open once he was on the plane and in his seat. There were three other items that made the flight a little smoother:

Kid- friendly ipad case

Families who have tablets probably already have invested in a kid-proof case. This one did the job well and was able to stand up on the lap tray. It also passed the test of being dropped a few times as well. Comes in a few different colors

Kid-friendly, wireless, bluetooth headphones

We are not HUGE on screen use at home, and don’t even use it in the car. However, flying and traveling during our vacation was going to be an exception. When I found these headphones on amazon, I thought I hit the jackpot. Also, since Chase has some auditory sensitivities, these served as a coping strategy as well. Not only did they have the criteria listed above, but they came in a pair that could connect to each other! They come in hard travel cases to protect them while not in use, and come one  cord to charge, and one to connect to each other so that each kid can hear the same audio. A bonus: there is an a adjustable sound limit of 96decibels max, so that it will never blow their eardrums accidentally. They also come in a variety of colors!

Inflatable footrests/pillow

Ok, I know this sounds ridiculous, but hear me out. When kids sit on a plane seat, their legs hang off of the seat. This makes them more likely to A) kick the seat in front of them, and/or B) want to jump down and leave the seat. I looked into these inflatable footrests and found a good deal on two of them. The older boys really liked them and even Camden was able lay down to rest comfortably. We used them for the van that we took from the airport in Montego Bay to our resort in Ocho Rios, which was about 1.5 hours away. These puppies inflate within 30 seconds, deflate just as quickly, and can be stored in a small bag. Major win for traveling.


Car seats

We would have to travel by van while on the island to a few destinations: MoBay to/from Ocho Rios, and a day trip to Kingston. The idea of taking three carseats/boosters overseas was a headache in itself. I didn’t want to resign to the local method “hold em in your lap” either. We decided to take the infant carrier for Camden, the backless booster for Carter and a foldable travel “booster” for Chase. I found the Mifold booster on Amazon, which may look sketchy at first, but has some good rationale to how it works. It brings the seatbelt down to their shoulder height instead of boosting them up to meet the belt. It has the convenience of fitting into a small bag once folded. Chase is very tall for his age, so I figured we could probably get by with it for the few rides we would make while in JA. I felt secure with it once installed and ended up working out really well!



I say this with some reservation, but at one time I owned 7 strollers. I know that seems excessive, but as we kept adding kids, our needs for traveling with them changed. Our go-to stroller for Camden right now is the Mountain Buggy Nano. This bad boy can fold down to the most compact size that is almost as small as my diaper bag. It unfolds with literally one hand! On top of that, it is versatile to accommodate all infant carriers, with no extra adapters needed! Camden usually travels in the stroller without the carrier, but going to/from the airport, this made for the perfect combo. The price point is also perfect. I’m in love with this thing.

Car seat protector bags

A good thing to have when flying with carseats or strollers is a protective, TSA-approved travel bag. A few years back when I traveled with Chase, I had a larger one for the carseat but somehow misplaced it just in time for the trip. Luckily, I also had an umbrella stroller bag, which miraculously fit both of the booster seats AND the infant carrier in so that it would stay clean and somewhat protected as checked luggage


So there you have it! Just remember, most of these are not necessities. You can totally travel with little ones without all of these extra items. However, for us, it made the trip with three much smoother and less hassle than had we gone without. What are some of your favorite tips, hacks and products for traveling? I’d love to know!