Why we Travel with our Kids
- Ashley @ Kealand Travel
- May 3, 2019
- 4 min read
We have 3 boys, ages 15, 6 & 4.
They can certainly be a handful on a good day, but for the most part we are very lucky and have good boys.
Just before we knew we were having our now 6 year old, we were lucky enough to have been offered a trip to Orlando, Florida with my parents the following March break. a few weeks after we booked our trip we found out that I was pregnant.

We did a lot of soul searching and thought that we didn’t want to not take our then 9 year old on the trip of his life time to go to Walt Disney World. We continued to plan for our trip for the rest of the 9 months I was pregnant. Between school for the boy, rep hockey, work for both of us and our pregnancy everything seemed to be under control. Just before Christmas my doctor took me off work as I had pre-eclampsia. Life all of a sudden seemed to be getting real. After an uneventful Christmas (I mean it was Christmas and we had lots of family visits and tons of presents for our 9 year old), we waited for the arrival of our little one.
Finally he was born (after a 3 day induction), in early January.
That's when the real fun began. For anyone who has had kids far apart in age, you know that the mommy struggles are real. Getting the oldest to and from school, extra curricular activities, packing lunches, play dates (do you still call them that with a 9 year old), not to mention that he is going between two households (as he is my stepson) and everything that goes along with having a new born. Doctor’s visits, feeding schedules, diapers, getting no sleep at all, you know all the regular stuff.
Our family trip was coming up fast, and I can honestly say that I was probably more excited than everyone else in my family to be going back to Orlando Florida.
The resort we stay at is called Vistana Sheraton Resort. It is my home away from home. My parents would bring my sister and I every single March break for the week, while we were growing up (and we still go when we can). I literally grew up there. We have what we call as our “Florida Family” of the same people that each and every year we would meet at the Super Pool during our same week 11 annual trip.
And now as an adult, and parent I was going to get to share this annual vacation with our boys. Our then 9 year old, wasn’t too sure what he was getting when we got on the plane that March to go to Orlando, but seeing his face was worth everything to me, and I am sure my husband too.
Our new born was 6 weeks old when we travelled.
I was very nervous to be traveling with such a little person. Aside from all the great memories we were going to make, traveling with kids comes with a whole lot of stuff you need to bring.
I am sure that everyone panics when they start thinking about everything you need to bring, but as a new mom, and avid traveler I thought I had it mastered!! BOY WAS I WRONG!!
We brought, our bucket seat with us and a stroller called a click it stand (it is a shell of a stroller that the bucket sit would click into place, with a net basket underneath. It was very light weight and was the best $50.00 we spent. I used it for both boys, even around town, instead of my very expensive stroller sometimes). I packed enough diapers to get us through the airport and to the resort, as I knew I would be able to buy diapers when we arrived, as well as wipes. I tried my best to keep our luggage light. I also knew that we had a laundry machine at the resort (BEST THING EVER), so I really didn’t over pack (well, according to me, my husband might have something different to say about that), and since I was breast feeding, I didn’t have to pack anything else. We also requested a crib to be in the room when we arrived. I did learn that the crib we got, was not what we had at home, and believe it or not, different countries have different regulations on what is allowed for cribs. Here in Canada, the cribs that have the slide down front rails are not allowed (we are talking 2013) but yet when we traveled to Orlando that is exactly what we got. Was our baby boy ok with it, he sure was. Did it take a day or 2 for me to calm my anxieties about it, sure did, but over all it was 7 days out of a lifetime and both Babyboy and I survived.
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raveling with a newborn, was probably the easiest traveling I have ever done. I even traveled with him by myself when he was 4 months old to Calgary, Alberta for 4 days when my sister was graduating from Medical School. Again I used the wonderful Click It stroller!!
Back to our first Orlando Trip as a family.
Being in one of my favorite places in the world with my husband, stepson and newborn was the best thing ever!! Did we struggle with some differences, absolutely, but over all it is a trip that none of us will ever forget.
I am so happy that we didn’t change our minds on the vacation, and that we chose to continue with our plans. Did our oldest make it to Disney – no he did not. Mostly because he didn’t want to go. He wanted to spend his days in the pool, getting a suntan and enjoying time with us as a family.
Forever memories that I know help make us all who we are today.
Best part is, that little 9 year old boy caught the travel bug and now wants to travel all over the world and enjoy everything that he can as a family with us.
A true blessing.
Chat Soon XO
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