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alyssa roloff.

Hawaii Family Vacation with a Toddler: Where We Stayed, Ate & Played

Travel

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Aloha! We traveled to Hawaii with our 2.5 year old recently and I’m here to share my tips & tricks for how to survive a long flight with a toddler & what we did on the island of Oahu, Hawaii. My mom grew up in Hawaii, so we have been fortunate to visit quite often! For this trip, our family was celebrating my dad’s 60th birthday! My family, my parents, my brother and his wife all went. It was great to have extra hands!

Travel

Tip #1: Go with family

Tip #2: Split up the flight if you can, or have somewhere to stay that would make it shorter.

The logistics of our trip:

We flew from Dallas, TX to Phoenix, AZ where my parent’s live to break up the flight. That flight was a few hours long, then we stayed the night at my parent’s house and flew out to Hawaii the next day. I do think the shorter flights helped, and it definitely helped having more people than just my husband and I to help and keep him occupied.

If you have a way to break up the flight, I would recommend it. The way back we took a flight that routed us through San Diego but we didn’t get off the plane – we sat on the tarmac for about 45 min then took off again to Dallas. In total we were on that flight for 9 hours and it was a bit rough for all of us.

We flew on Southwest Airlines.

Car Seat & Stroller

We brought our travel car seat – we only use this when we travel because it was cheap and we don’t care about it getting banged up. Our Nunas stay at home in the car. The travel car seat is extremely light weight and easy to get in/out of cars and carry through the airport. It also keeps him contained on the plane when he would otherwise want to run around and not stay in his seat. Then we used it in our rental car. We also brought our travel stroller to use through the airport.

On the flight

I was the most worried about the long flight with our 2.5 year old. And it went surprisingly well! Maybe the key is to have very low expectations haha!

Snacks

Bring a TON of snacks. I packed a full lunch in his lunchbox on the way there – a peanut butter sandwich, string cheese, fresh fruit, crackers etc. I also packed a bag with bars, pouches, fruit snacks, and fun snacks he hadn’t seen before. I rationed out snacks for the flights in these clear bags and packed extra bars & pouches in my suitcase so he didn’t see them/want to eat them all at once.

Activities

I loaded up on new activities for the plane ride. Toddlers have very low attention spans so having a ton of things to do was crucial and definitely helped keep him entertained on the flight! We also let him watch some kid shows on the in-flight TV which he preferred to the movies we had downloaded on Disney+. I think having something new he’s never seen before helps for flights.

If you get lucky & your child naps on the flight – amazing! We thought he would, and encouraged it throughout the flight, but he fell asleep right when we were landing.

Here are some of the activities I bought – some from Amazon and others from the $1 section at Target.

Play-doh, window stickers, window clings, reusable stickers, math activity with dry erase pen, water coloring, books, and iPad with kid movies downloaded.

Shop all my Kids Travel here

Hawaii – Activities

Once we were there we hung out at the resort pool and beach, played in the sand, drove to the North Shore, looked at sea turtles, got shave ice at Matsumoto’s, toured my mom’s old high school, went shopping, toured Pearl Harbor, explored different beaches, and went to a luau at the Disney Aulani Resort on our last night!

🌺 Beach
🌺 Pool
🌺 North Shore
🌺 Matsumoto’s Shave Ice
🌺 Shopping
🌺 Pearl Harbor
🌺 Luau at Disney Aulani Resort

Nap time / sleeping

My son has never really slept well when we travel, so he sleeps in bed with us. It’s just easier than fighting and getting up multiple times, and it’s understandable that he could be scared in an unfamiliar environment.

For naps, he will usually sleep when we travel but now that he’s outgrown a pack n’ play it’s a little trickier. We brought this travel inflatable bed and he did sleep in it for a nap & most of the first night. After that, he only slept when we drove to the North Shore or other beaches (about a 45 mim drive from our hotel). If you have a toddler who is refusing naps, try to plan your drive for their nap time and see if they’ll sleep in the car while you drive around and look at the pretty scenery.