Tips for Going on Vacation with a Toddler!


toddler sitting on an airplane watching an ipad and holding a toy airplane - tips for going on vacation with a toddlerMy husband and I love to travel and before our son was born, we’d take a few trips a year and try to pack as much into our trips as possible. When our son was born, we dreamed of the trips we’d take and having our son experience travel with us. Here’s how we decided on our destination and what we did to make our vacation enjoyable for us all.

Deciding on a Destination

Our goal was to rest and relax. Knowing this was our son’s first trip, we wanted a quick and direct flight. Knowing these priorities helped narrow down our destination – and we got direct flights from Boston to Fort Myers. We were fortunate to stay at a family friend’s home for the trip, so having the comfort of a full house versus a hotel room was a great bonus for our trip.

Plane Ride Prep

The three of us sat in one row with our son in the middle. We kept him in the stroller through the airport and then gate-checked it before boarding. This was great to help keep him contained as we navigated the parking garage and airport. I packed a backpack full of snacks, activities and books for my son. We also got him some headphones and had a tablet stocked with his favorite movies and shows as a backup plan if he got antsy. This left the adult carry-ons for diapers, changes of clothes, and our personal items. I also packed some lollipops for take-off and landing to help his ears and that worked the best.

Car Seat

We knew we needed a rental car when we landed in Florida and after much debate, we decided to gate check our car seat instead of renting one. Checking the car seat with your luggage can damage the car seat in transport. My husband had to carry it through security, and it was very cumbersome. I’m happy we brought our own car seat because we were familiar with installing it, and using it while on our trip. This was the safest option for our trip. We did buy a car seat carrier bag on Amazon so my husband could carry it as a backpack and that was a lifesaver.

Packing List

I brought his sound machine, favorite books and blankie to keep his night routine familiar in a new place. I also packed his diapers/wipes in our checked bag and used a disposable diaper pail (Munchkin brand) to help keep the trash from stinking at our home for the week. We didn’t pack any toys outside of what was in his plane backpack and that was enough for the week. If you’re traveling with younger children and need high chairs, pack ‘n plays, etc… you can search rental companies near your destination for those items to be delivered to your hotel. Some hotels will have pack ‘n plays on hand as well.

Deciding on Your Itinerary

We had one activity planned per day and mapped out our vacation around that. Again, we wanted to relax, so having one firm daily activity gave us some structure, but still allowed for flexibility if we wanted to hang out at the pool or check out a different restaurant. We took into consideration our son’s schedule and nap time, but didn’t plan around it. If he fell asleep while we were out, great. He skipped most naps this week, but overall was fine and helped let us experience more on our vacation.

Due to the pandemic, we waited much longer than expected for our first family vacation. In some ways, I’m glad we waited until he was a little older before jet-setting. It definitely saved on the hassle of having more stuff to worry about for him (bottles, where he could sleep, high chairs, etc…).

This was a special trip for our family because after we booked our flights, I found out I was pregnant! I know we won’t be traveling again for a while, but I am looking forward to our first trip as a family of 4!


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