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In July of 2022, we took our 18 month old with us to the Big Island, Hawaii! Keep reading below to learn about traveling to Hawaii with a toddler!
So, this trip has been planned for over a year… and the destination changed many times before we booked Hawaii. We knew we would be traveling in the summer to celebrate my sister graduating from Law School (Go Cortnee!) So how did we end up on Hawaii?
Initially, we had planned an entire trip to Ireland and had started booking our hotels and Airbnb’s. But, this was when we thought we would be traveling in May. However, my sister had mandatory prep for her state exam so we wouldn’t be able to travel until the end of July. When we learned this, we cancelled our reservations and started rethinking Ireland. Our itinerary had A LOT of driving and relocating and we knew it would be a lot of work with Kennadi.
So, we then decided to go to Paris! A dream city that most of us in the group had not traveled to before. We started considering Paris and Cannes/Monaco. Again, we had this fully planned and started booking hotels again. The only thing we were unsure of was if the flight prices would decrease. None of us were willing to spend $1500+ on flights when you used to be able to travel to Europe for half that price.

Well, plot twist number three…. We BOTH found out at the beginning of the year that we were pregnant (if you missed it, read the full blog post here.) Once we knew this, both of our husbands were not comfortable with us leaving the country when we would be 7 months pregnant. So, back to square one.
My sister initially chose Boston and Pittsburgh when we decided we would be staying within the US. But again, the flight and accommodation prices were insanely high and didn’t seem like they would be dropping much. I had previously been to Boston in 2020 and knew just how much walking (and humidity) that trip would entail. Didn’t sound too fun while 7 months pregnant. So, at some point Hawaii was suggested.
She had already been to Oahu and Maui so we looked at the other islands. The Big Island stood out because it offered so many different things to do. My sister didn’t want to just lay on the beach every day but rather, explore and see different things. The more we researched it and watched pricing, we knew that is where we would be going!
Keep reading for our experience flying with an 18 month old, accommodations, and things to do on the Big Island, HI!

Big Island, Hawaii with a Toddler: Packing and Luggage
Packing for a trip with an 18 month old is not easy. We had SO much to bring and I truly felt we had cut our list down significantly. We knew we would be buying most essentials once we arrived instead of packing them (diapers, wipes, snacks, food/milk, etc.)
Since we purchased Kennadi her own seat, we had a bigger allowance on carry-on items. We also knew we could check a third suitcase even though we planned on just checking two suitcases. However, our dilemma was (1) how in the world are my husband and I going to carry all of this through the airport and (2) how will this all fit in the mid-sized rental car once we arrive (my Mom and her boyfriend would be in the rental car with us too so we had to think about their luggage as well.
This was our list of everything:
- 2 checked suitcases (to fit everything for us 3)
- 1 carry on suitcase (with valuable essentials: Slumber pod, baby monitor, travel booster seat, life jacket, etc.)
- 1 under the seat rolling carry on (for Kennadi’s toys, snacks, tablet, diapers/wipes, blanket, sound machine, and change of clothes)
- My diaper bag (my personal stuff/all electronics chargers/cords)
- Husband’s personal backpack (his stuff and first aid kit)
- Yeti cooler (Kennadi’s milk and food)
- Car Seat (and strap to attach to carry on suitcase for rolling through the airport)
- Stroller
- Backpack carrier (for hikes)
So, as you can see, a lot of freaking stuff for two people to carry. Even with dropping two suitcases at the counter, we were going to have a lot to take through security and get to the gate. We knew our family would be able to help but it was just overwhelming the amount of stuff we had.

Even with buying stuff there, we really struggled to make everything fit (and stay under 50 lbs.) If you don’t have a luggage scale at home, buy one! This is the one we have and it is SO worth it. Thank goodness we weighed stuff at home because both of our checked suitcases were 10 lbs. over weight. We had to do a lot of rearranging between the checked suitcases and the carry on. We showed up at the airport with our suitcases at 53 lbs. and luckily, they took them without hesitation.
We flew out of LAX and chose to stay down there the night before so we wouldn’t have to wake Kennadi up early the morning of the flight and have her sit in a car seat in two hours of traffic before sitting an additional five hours on a flight. When we got to our hotel room, my husband and I were both so overwhelmed with all our stuff. We were trying to figure out how to cut down and my Mom suggested we leave some baby gear behind and rent it once we arrive.
Kennadi is not a big fan of her stroller (again, just does not like being constrained) however, she loves the backpack carrier. We were going to have to carry the carrier through the airport anyways to gate check so we decided my husband would wear her in that through the airport and we would leave the stroller. We chose to rent a stroller for the week through Aloha Kona Kids. It was one less thing to bring to the airport and fit in the rental car.
We only used the stroller twice on the trip so we could have gone without it but if you are taking kids to the Big Island, definitely check out all of the items you can rent from Aloha Kona Kids!


Big Island, Hawaii with a Toddler: Flights
I had fully intended on writing an entire blog post on how to keep your 18 month old entertained on flights… well, Kennadi sure did not cooperate and hardly anything worked for us. We flew with her to Costa Rica when she was 7 months old (full blog post here) and she was SO much easier than at 18 months! So, I won’t be writing a whole post but will share here what I had packed and planned.
We chose to purchase a seat for her. Neither my husband or I wanted to have her in our lap the entire flight. And we knew she would not cooperate if we attempted it. On the way there, we brought her car seat on the flight. We were going to need it anyways in Hawaii for the rental car but we also thought that would be our best option for getting her to nap on the plane. Well, as you will read below, it didn’t work.
Kennadi HATES being confined and constrained (sounds perfect for a plane right?) She absolutely despised the car seat on the plane ride. We could not keep her in it without her hysterically screaming. She just climbed all over it the whole flight so on the flight back home, we ditched the car seat and checked it at the counter with our luggage. I will say, she did better on the flight home (only for the first hour) without the car seat and just sitting (and by that, I mean climbing all over) in her window seat.
As you will read anywhere, it’s always recommended to book a flight that coordinates with nap and bed time. We did that, and it didn’t matter. Kennadi refused to sleep on the plane. Milk, blankets, sound machine, Benadryl… we tried it all and no success. She was way too interested in what was going on around her. There were a few times she would start falling asleep, and then once she realized it, would wake up and be back to full freak out mode. So. Much. Fun.

With that, a five hour flight with an overly exhausted toddler was not all that enjoyable. I also think success on a plane depends on your little one’s personality and temperament. Kennadi is a toddler that is extremely hard to keep entertained on a daily basis. She will focus on a toy or screen time for about a max of ten minutes and then is on to the next thing. The plane flights were no different.
I packed a ton of new items for her including different activity books, stickers, post it notes, fidget toys, sensory toys, interactive toys, and an Amazon Fire kids tablet. I also knew to bring a ton of snacks (and dum dum lollipops!) and saw a neat idea to use a one month pill holder to fill with small snacks. I REALLY thought this would help keep her entertained as she loves to open and close things but, she didn’t really care about it. She messed with it for a few minutes, ate some snacks out of it, and then was over it.
Our flights consisted of 5-10 minutes of entertainment at a time mixed with running up and down the aisles and many tantrums while fighting sleep. Thankfully, the flight attendants were amazing and so incredibly helpful! And there were two other little ones struggling just as much as Kennadi was. Hopefully the pictured items will help your little one(s) more than it helped Kennadi!


Big Island, Hawaii with a Toddler: Accommodations
When visiting the Big Island, there are two main parts of the island to choose from: East and West. Most people suggest splitting your time between the two sides to see everything. We only had a week so we chose to stay on the West side where most resorts and towns are.
With choosing the West side, we planned two different days of driving to see the volcano and waterfalls on the East side (we ultimately chose against the waterfalls once we arrived, more on that below.)
There are a ton of options for hotels and resorts in Kona (West side.) My Mom owns a timeshare so we are used to condo type properties when we travel. It is especially nice with a toddler to have a separate bedroom and living area as well as a full kitchen.
For this trip, we didn’t book through my Mom’s timeshare because we ended up finding an extremely affordable package deal through Hawaiian airlines. Our package included round trip flights and 7 nights at the property (and was cheaper than if we booked the property on its own!) We also chose to book rental cars; an absolute necessity for the Big Island!
We stayed at Kona Coast Resort in Kona. I will get to the good first: the property grounds were beautiful, housekeeping was extremely accommodating to all requests, our rooms were huge (1600 sq. ft. for a 2 bedroom,) and it was centrally located to everything on the West side of the island.
The not so great: the pool on site was nothing special, no beach access, and the rooms were extremely outdated. Oh, and the floors in our room were dirty. As in, walking barefoot on the carpet turned your feet black instantly. There was no housekeeping service (you could call to request things but there was no cleaning service) so my husband ended up calling for a vacuum and mop. Even with him cleaning, it didn’t fix how dirty the carpet was. And was just ridiculous to have to clean on vacation.
The property needs an entire facelift and renovations. But, for the price we paid, it was worth it. However, if we come back to the Big Island, we will find a different place to stay.


Big Island, Hawaii with a Toddler: Activities
On to the fun stuff! There is SO much to do on the Big Island! It was hard for our family to really narrow it down and decide what was most important without having an exhausting itinerary. I have outlined some of our favorite beaches we visited and activities/tours below!
- Hapuna State Beach
- This is the largest white sand beach on the Big Island. Because of the volcano, most of the island is extremely rocky, including the beaches. This beach is one of the exceptions! It was an hour drive from our resort so it made the day a little longer but the beach was beautiful! The walk down from the parking lot is not easy! It is quite a trek. And, we read there was food on site. There was not; we had to hike back to the car and visit the Westin nearby to have lunch at their poolside restaurant. Just something to keep in mind if you don’t pack your own food.


- Manini’owali Beach / Kua Bay
- We had originally planned on visiting Hapuna a second time but none of us really wanted to do the 1 hour drive again. We google searched for other white sand beaches and came across this one. We wish we had discovered it sooner! It was only 30 minutes from our hotel and was beautiful! The parking was much easier and the snorkeling was amazing. The only downside was this beach gets crowded so get there early!




- Hawai’i Volcanoes National Park
- In my opinion, you can’t visit the Big Island without seeing the volcano. It was a long two hour drive (trying to keep Kennadi entertained) each way but was worth seeing. There are so many different hikes and things to see within the park. We spent a half day in the park and chose to see the steam vents, different lookouts, and my personal favorite; the Thurston Lava Tube.


- Punalu’u Black Sand Beach
- We visited this beach on our drive back from the national park. It is the only black sand beach and is known for the sea turtles! We learned that it isn’t really a beach for sun bathing and swimming. We had packed swimsuits but opted to stay in our hiking clothes while we spent some time on the sand in our chairs. Kennadi loved the sand (more like pebbles) and we all enjoyed seeing the sea turtles.
- South Point Cliff Jump
- This was on our itinerary as it was also on our way back to the hotel from the national park and black sand beach. But, it would be a one hour detour round trip. Once we left the beach, it was already 3:30 and all of us were exhausted. My husband and brother in law were going to do the cliff jump but it was crazy windy (as seen in the volcano pictures above!) So, we all decided to skip this as we didn’t think it was worth the extra hour detour.
- Waterfalls: Akaka, Rainbow, and Peepee
- The volcano was a full day (and exhausting with Kennadi) of driving and sitting in the car. We had planned on doing another full day of driving to go back to the East side and see the waterfalls. However, after our day of visiting the Volcano, all of us were a little hesitant about another full day of driving. We ultimately decided to skip seeing the waterfalls and had a beach day instead. I am sure seeing the waterfalls is worth it (maybe if it wasn’t so far from our hotel and we didn’t have an 18 month old that hated her car seat.) Since you can’t swim in the falls, we figured it wouldn’t be worth two hour drive each way to just look at a waterfall for a few minutes.


- Night Swim with the Manta Rays
- This was by far my favorite thing we did on our trip! If you google it, you will find a ton of tour options. For us, it was a little more challenging finding a tour that allowed pregnant women and toddlers. We booked ours through Ocean Encounters and it was amazing!! There was no age restriction; we just had to bring a life jacket that fit Kennadi for the boat ride. They told us she would be allowed in the water as well but we opted against it. The tour was during her bed time and she wouldn’t have been able to see the manta rays. She enjoyed staying on the boat while we were in the water. Trust me when I say, you HAVE to do this! It was unreal having massive Manta Rays swimming against you.


- Golfing at Kona Country Club
- The guys booked golfing for one of the days (while us girls shopped.) I don’t have much to say about this but they were all extremely impressed with the course and grounds at Kona Country Club!


- Royal Kona Luau
- You can’t go to Hawaii and not go to a luau. We had researched the top ones and booked Royal Kona Luau. The food was delicious and the entertainment was pretty good. Kennadi loved the food and was entertained the whole time!
- Kona Brewing Co.
- This was a top favorite for food and drinks; we visited on two different nights. They have a large menu, tons of drink options, and the brewery/restaurant is kid friendly!

Big Island, Hawaii with a Toddler: Schedule
One last thing about traveling with a toddler; expect their schedule to go right out the window. When we are at home, Kennadi is on a perfect routine and schedule. My husband and I did not stress about this at all on vacation. She was never in bed “on time”, didn’t take one normal nap, and her eating was all over the place. But we didn’t care; she napped when she napped (mainly in the car on drives) and went to bed once we were back from dinner each night. It was a three hour time change for us so we all struggled the first day but after that, Kennadi seemed to be adjusted to it.
She got WAY less sleep than she does at home but all things considered, she did pretty amazing on the trip. She absolutely had her over tired, tantrums, and meltdowns but nothing that wasn’t to be expected. When we got back home, she slept SO much for the next week. She usually sleeps 12 hours at night and takes one 1.5-2 hour nap. Well, vacation must have worn her out because for over a week, she slept 14 hours at night and took 2-3 hour naps. No complaints over here; it was nice to get caught up on things once we got home!
Well, that about covers our trip! I am sure there are things that I left out so if you have any questions, just comment below or reach out on Instagram! I would love to know if you are planning a trip to the Big Island; especially with little one(s)! The hardest part, by far, was the flights. Aside from that, our week in Hawaii was incredible. We look forward to going back again one day!
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