This month Paul and I embarked on a family vacation to Hawaii. The  tripped encompassed a five-hour flight, rental car, and off-site lodging, plus, it was all achieved with a 15-month-old in tow. The trip was one of our best, most enjoyable family vacations we’ve ever had and I would love to share some helpful hints that I learned while traveling with our toddler.

I know traveling with a toddler can be intimidating for any parent, even Paul took some convincing, but it doesn’t have to be a scary experience of “what-ifs.” Your trip can be a fun experience that will provide you with unforgettable memories like ours. Here are some of the things I learned during our Hawaiian adventure.

Booking Your Air Travel, Choosing Your Timing

On our flight to Oahu I tried to book our flight so it would overlap with Sage’s nap time. The travel time worked out, but unfortunately, there was too much excitement for Sage to go down for his nap. However, for our flight home we booked a red-eye flight and this worked out perfectly! Our flight departed at 10 p.m. so we arrived in Los Angeles at 6:30 a.m. The airport was very empty around 8 p.m. for our departure, which made check-in and security a breeze.

Here are the specifics of that return flight:

  • Sage fell asleep in the car ride  to the airport (normal bedtime is 7:30 p.m.) and remained asleep while we returned our rental car and shuttled to the airport.
  • He woke up when we were forced to take him out of his carseat to go through security.
  • While waiting to board the plane we fed Sage dinner and read lots of books.
  • Once on the plane Sage was entertained through take-off and fell asleep almost immediately after they turned the lights out.
  • He slept the remaining plane ride and once we got home he took a five-hour nap!

I will certainly be booking red-eye flights in the future if it makes sense to do so, (such as traveling from the west coast to the east coast).


Traveling With Toddler Gear

If you are a parent, you know its pretty much impossible to travel light with a kid, but here are some ways we lightened our load. If your toddler still fits in his or her infant car seat, bring the infant car seat. Even though we have upgraded to the convertible car seat at home, Sage still technically fits the height/weight restrictions of the infant car seat.


We brought this more lightweight and easy to carry car seat and hooked it right into the stroller, (just like old times!) to make our way through the airport with one less (heavy) item. We also brought the Pack ’n’ Play, which we checked for free at the airline check-in counter. Outside of the baby gear, we were able to fit all of Sage’s clothes, diapers, wipes, bath towel, and key toys in our checked bags. We filled the diaper bag with baby essentials for the plane ride which we used as one of our allotted carry-ons.

Toddler Essentials for the Plane

The two most important items for the plane ride are food and books! We packed a large lunch box full of Sage’s favorite (and not too messy) foods. Food essentials included; bananas, individual packs of Justin’s Almond Butter, Lara bars, medjool dates, clementines, grapes and strawberries.

We also packed several of Sage’s favorite books, which he can read over and over and over again. Bonus: the plane is full of entertaining things for curious toddlers. Sage loved opening and closing the window shade and turning the TV in the headrest on and off. Near the end of the plane ride to Hawaii we did lots of walking up and down the aisle.


Choosing Your Accommodations

I can not recommend AirBnB enough. It worked perfectly for us, and allowed us more space for less money than a hotel. Sage does much better in his own room so I wanted to find a place that was at least a one bedroom. We set-up Sage in the living/kitchen area and once we put him down Paul and I retired to the bedroom (which luckily the bathroom was connected too) for some relaxation.

Our AirBnB also had a little fenced in yard which was very convenient when we were getting things ready in the morning to go out for the day. When Sage started to get antsy, we could open the door and let him play outside while we finished packing.

Kid-Friendly Travel Activities

We chose to travel to Hawaii so we could be outdoors all day, everyday. Sage likes nothing more than being outdoors. Aside from time spent in the car getting to locations, we were outside. With Sage in the Ergo carrier on Daddy’s back we did lots of hiking. We also spent lots of time swimming in the warm ocean.


One day we went to a park so Paul could freerun and it just happened to be across the street from Hawaii Children’s Discovery Center, so while Daddy did his freerunning, I took Sage to the Discovery Center to play for a few hours, he absolutely loved it!

For most of our meals we ate at the Woodstock Fruit Festival; which was the other motivation behind our trip. The festival is a raw vegan week long camp where they provide all of your meals. Its nothing but fresh fruits and vegetables and most meals are eaten outdoors on the grass. It doesn’t get more toddler friendly than that!


Overall, there isn’t much I would change about this trip. I am not trying to undermine the effort it requires to travel with a toddler, but I hope my readers realize it’s not impossible and most likely your toddler will travel better than you expect.

So go ahead and plan that next family vacation, or share your travel tips in the comment section below!