Hawaii With Kids

Flashback, it’s 2021 and we have been living in this bizarre Covid world for a year. The travel bug in me is screaming to go on an adventure, my kids are going stir crazy, and we are in desperate need of a break from this new reality we are living in. So this mom got a wild idea. Why not trek halfway across the pacific to the newly reopened Hawaiian Islands with 2 little kids?

Ya’ll, traveling with kids is no joke. To do it even semi successfully takes a lot of planning. To do it during a pandemic is a herculean effort and feat. Don’t think that it stopped me though. Where there’s a will, there is a way. It was a really amazing, quiet time. The people we spoke to were so thrilled to have visitors back to the islands (I know not everyone shared that sentiment). The trip ended up being a big success and helped us make it the rest of the way through the pandemic. Thank goodness we are on the other side of it. Since the world has found balance again, we have been blessed to return to the beautiful Hawaiian Islands. This time with four kids in tow.

Here are some tips and tricks I learned when planning both vacations to the islands with my kids.

When booking accommodations, I look for at least partial kitchens, washer and dryer in the room, basically a home away from home while still having many of the hotel type amenities. Always remember to call ahead to ensure they have a crib if you need it. There are also people who rent all types of child gear and will deliver it directly to your accommodations. Just be sure to plan all of this before you get there. I made the mistake on a different trip (not to hawaii) to call ahead for a pack n play. They didn’t have any left! I’ve never made that mistake again.

For me, the most daunting part of the trip was the long plane ride with squirmy kids. I never want to be “that parent” on planes. So I prepare myself as best as I can for that stretch of time. It all begins the week before, when I start my packing process. I make a list for each person’s checked bag and carry on. I pick one person each day and pack them completely. My husband has offered to help with this but I find that I enjoy it and I like knowing where everything is if I need it in a pinch. 

Here is a summary of my packing lists for my kids based on their age.

0 to 12 months
Checked BagCarry On
BottlesFormula (extra)
DiapersBottle Cleaner
Swimsuits- at least 2Socks/ shoes
SunscreenSpinny Adhesive Toys
Pajamas Crinkly Books
Summer OutfitsSnacks (for older babies)
Sound MachineBlanket
NightlightChange of Clothes
Swaddles/ Sleep SacksBaby Carrier- Bjorn
1 to 3 years
Checked BagCarry On
Swimsuits (at least 2)Tablet
Summer OutfitsHeadphones
Diapers or UnderwearSnacks
WipesFavorite Stuffed Animal
SocksFavorite Blanket
Flip FlopsFavorite Toys
Sound MachineCrayons/ Paper
4 to 7 years
Checked BagCarry On
Swimsuits (at least 2)Tablet
Summer OutfitsHeadphones
UnderwearPre Packed Snacks
SocksFavorite Stuffed Animal
Flip FlopsFavorite Blanket
GogglesFavorite Toys
PajamasCard Games
 Homework/ Activities
Bubble Bums

My usual packing lists will break down the specific number of each item based on the number of days we go. For younger children, I usually pack one extra outfit per day. Older kids I pack 2 extra outfits for the week.I always use packing cubes to help sort the clothes and make it easier to find things. 

For their carry ons, I make sure they are either in rolling bags they can pull themselves or in bags I easily stack on my roll on carryon. With really littles, we bring a stroller and manage to stack below and all around the stroller as well. 2 adults, 4 littles, we look chaotic, we are chaotic, but we get it done! 

The Airplane Ride

We arrive at the airport with plenty of time to spare. As soon as I can, I put a motion sickness patch on my kids and myself. The last thing I want to deal with is barfing on a plane. We arrive early because you never know what obstacles await and it’s better to have sufficient time than to be stressed trying to run to your gate with little ones in tow. One time, our recently purchased (used) stroller didn’t pass the swipe test and I almost missed the plane. Lesson learned! With the “extra” time, we make sure our kids get their energy out, go to the bathroom, and understand what is about to happen. We make it sound super fun, like a roller coaster.  

We always take advantage of pre-boarding. While I hate the idea of being on the plane any longer than necessary, I hate even more, the idea of rushing to get everyone settled while everyone waits on me to hurry up and be done. This way, I can make sure each kid has their carry on at their feet, their stuffed animal, blanky, and tablets set up. Then I get myself settled in. By this time, we are almost ready to taxi. We usually sit straight across in a row so I can see everyone and they can see me. We have done it the row behind and that was fine too but not my preference. 

My kids eat way too many snacks and have way too much screen time, but it keeps them occupied and happy. I encourage everyone to take a nap at some point on the plane ride. I tell them, we’ll get there sooner if you fall asleep! Whether traveling with 2 or 4, I never read a book or even watch a show. I spend the entire ride catering to someone’s needs. Whether that’s a sleeping baby on my chest, or grabbing the next activity for a little one. I’m sure once they’re older, it won’t be as demanding. As soon as we arrive at our destination though, I am wiped! 

The Arrival

If we rent a car, we take advantage of using their car seats. If we don’t, we bring our Bubble Bums inflatable booster seats! They are compact and fit in their carry ons. For smaller ones, we use their stroller that connects to their car seat so we have it straight from the gate. With little ones, there are a lot of bags and gear to lug around. It is doable if you pack smart and think ahead.

If we rent a car, we make a quick stop at the grocery store to grab snacks and pre-made food to sustain us for the meals we don’t want to eat out. If we take a ride share, one of us will go later and grab the essentials. 

When we arrive at our hotel, the first thing we do is get our swimsuits on. After a long flight, these kids have energy built up inside! We settle in a little and then head to the water. We keep it very easy that first day and either order food or eat on site. 

The Vacation

Our kids are perfectly content to spend the entire vacation in the swimming pool. We always make a point to get to the sand and play in the waves, beach warnings permitting. People often leave tubes and sand toys around when they leave, so we take advantage of their kindness. When we leave for home, we set them out for the next family to claim. It’s important to remember to sunscreen regularly. My children don’t really burn but I apply sunscreen every hour anyways. Gotta protect their skin!

We love to find little hikes, blowholes, or other easy to access viewpoints for our kids to get the full experience. Luau’s are actually really fun with kids. They are entranced and I just love watching their faces as the dancers perform. So much joy! We always make sure to get Hawaiian Shave Ice and to check out the local sea life, from a respectful distance of course. Every single night, we make our way to the sand and watch the sun set. I wish I did this at home more often, but here, it is a must.

On our trip to Hawaii with our first 2, we used The Nanny Connection agency to hire a babysitter so we could get some alone time. We stayed on property in case of emergency but it was so nice to be able to just be together. I know a lot of people are nervous about the idea of doing something like that, but I used to be the nanny that came to hotels to watch people’s kids. So I knew what went into vetting the people who do it. I also used my gut feeling when meeting the sitter. I have a scary on point sense of people when I meet them. Thankfully it all worked out, we had awesome sitters that my kids really enjoyed. The second time around, with all 4, we brought our babysitter from home. I wanted someone I knew could handle all 4 and whom everyone was comfortable with. We also had both sets of grandparents on this trip so there was no shortage of sitters! 

Preparing to Leave

This is the worst part of every trip! I swear a little bit of my soul stays behind when I leave. I usually try to find a place that has a washer and dryer in the unit. On the last day, I do laundry at my leisure so that when I get home, we just unpack our things directly into our drawers. It makes coming home a little less painful. I repack everyone’s carry on to make sure everything is easily accessible. 

Each island of Hawaii has something special to offer. The islands are my happy place and I am so blessed to have been able to share them with my children. The warm, humid air, the quiet pace of life, the aloha spirit are just a few of the many wonderful things about Hawaii. I don’t know that our vacations would be as fun or restorative if I didn’t take the time to plan it out. I am able to get us there and back without much stress on my end.

What is the most daring place you ventured with your young ones? I’d love to hear from you.

Join me over on Instagram for future updates and other content.