How to take two infants on a Maui vacation and not hate it

I think a lot of parents of twins do not attempt to travel for fear of the effort involved. However, before the twins are 2 years old is the best time to travel because they are free and don’t have school. I’m writing this to help parents of twins learn from our successes and also our mistakes.  For regular reader’s of this blog, this post is off topic. If you’re not interested, feel free to skip reading this one.

We are wrapping up our two week trip to Maui, Hawai’i. We travelled with four adults and two infants, which created some unique challenges. Traveling with young kids is hard because they have a strict eating/sleeping schedule and require a bunch of extra gear. Because of the difficulties of traveling with young kids, we almost decided not to go, and it took months to prepare for the trip. I try to capture what worked well, what didn’t work, and what to remember for next time.

Gearing Up

We (my wife) spent a lot of time researching and experimenting to find great gear for infant travel convenience. The most critical pieces of gear are the stroller, car seats, and high chairs because we use these items multiple times every day, and cannot do without them.

Car Seats

2X Diono Radian R120 All-In-One Convertible Car Seat

We really like these car seats for a few reasons. They are a little heavier than other car seats, but they are have a unique feature. They fold flat. This makes a big difference when you need to carry two! These seats are aircraft compliant. They work backwards-facing and as a front-facing booster, so the kids can grow into them.


UPPAbaby Vista double stroller.

We did a ton of online research and tried a few strollers before settling on this one. It is super modular, so the kids can be switched around. It’s sturdy and lightweight, easy to fold.

We have the 2016 model which has bulkier rear wheels. I kinda wish I could upgrade to 2017 just for slimmer wheels.  I have accidentally run over a dog’s tail with the fat tires on our stroller. (not fun)

To match our stroller set up you need these items:

High Chairs

2X Summer Infant Pop N’ Sit Portable Booster Seat

These are great for travel because they fold up like camping chairs. They come with straps for attaching them to regular chairs, turning them into portable high chairs with tray tables. Super convenient for meal time!

Getting There

Buying Flight Tickets

This time we chose to go with Hawaiian Airlines. There are other options besides Hawaiian air for getting to the islands, but to me it’s totally worth the extra dollars to fly Hawaiian. Hawaiian music, Maui onion chips, free rum punch, all help set the mood. The staff was unfriendly at times and we are considering trying Virgin America next time. As such, this post focuses on our Hawaiian Airlines ins and outs.

One of the reasons it’s great to travel with infants is they are free! You can have kids under 2 years old sit on your lap, and you don’t need to buy them their own seats (unless you want to). When choosing where to sit, be sure to get aisle seats. The kids can get antsy, and it’s very helpful to carry them up and down the aisle.

In addition, the kids aren’t in school yet. This means you can plan your trip in off-peak-season to save money and avoid some crowds. While booking our flights months in advance we found a dip in price in early September. We believe this is caused by a drop in demand since it is just after school starts in the fall and just before the winter season. During winter, ‘winter birds’ travel to tropical destinations to escape cold, east-coast weather.

If you forget to add the infants to your flight reservation, call Hawaiian Airlines customer service to do it. It will save you time when you get to the airport, since you will be able to quickly print boarding passes for everyone including the infants. Some airlines ask for documents to verify infant identity and age, such as immunization card or birth certificate. For Hawaiian Airlines, having the documents is optional.

In preparation for braving the 5 hour flight from California to Hawaii, we took the twins on a 1 hour test flight to visit grandparents. This helped us learn some lessons the hard way. We learned to sit on the aisle seats, and to be ready with something for them to chew on to pop their ears. The five hour flight to Maui was not their first time in the air!

Getting to the airport

Things did not go according to plan. We left 3 hours before take-off. To get to the airport, we hailed a Lyft Plus (6 seats), hoping for a minivan.

From our experiences, we prefer Lyft over Uber. Overall, Lyft drivers seem happier and more helpful, and the rates for rides are slightly less. Lyft is not available as widely internationally, but it is available in most of the US.

Our summoned Toyota Highlander showed up, and it seemed impossible to fit all 6 of us, our luggage, and the driver. We sent two adults and most of the luggage, and hailed another Lyft to pick up kids and stroller and two of us remaining. Lucky for us, a minivan showed up. It took a few minutes to hook up the car seats, load up the kids and be on our way. About an hour after we set out, our group and luggage all made it to the airport terminal.

Checking in and Checking Bags

The car seats were folded up and packed into cardboard boxes. Hawaiian Airlines does not charge for checking in car seats. Each checked bag does cost a fee. Hawaiian Airlines credit card holders can check 1 bag for free (up to 50 lbs.).

Checked Bags up to 50 lbs and 62 linear inches

  • 1st checked bag $25
  • 2nd checked bag $35
  • 3 or more checked bags (per piece) $100

Tip: coming back, our checked bag was way overweight. They asked us to trim it down to 52 lbs. So, Hawaiian Airlines employees will accept up to 52 lbs. on the scale, while the official rule says 50 lbs.

Getting Through TSA Checkpoint

We made it through TSA fairly quickly. They did poke around our baby food, but nothing was confiscated this time. Before our 1 hour test flight, TSA confiscated the twin’s tube of sunblock lotion since it was over the allowed size. Be prepared to take everything out of the stroller and put it through the x-ray scanner, including the stroller itself, if possible. Our stroller is too wide to go through the scanner, so an agent has to manually inspect it every time.

Family Boarding

For Hawaiian air, families can board after wheelchairs and unaccompanied minors. It takes a bit of extra time to get the kids and carry-on luggage settled. Plus, you will need extra time to take care of the stroller (see below).

Gate checking the stroller

The kids can stay in the stroller up until boarding. At the end of the loading ramp, we met an airline employee who tagged all three pieces our stroller. We took the kids out of the stroller and disassembled it just before entering the plane. It’s a little bit tricky getting to seats afterwards because you have to carry two kids, diaper bag, plus all of your other carry-ons to your seats.

Then began our 5 hour flight to Kahalui. Despite our best efforts, we endured a good amount of crying during the 5 hour flight.

One tip is to have a bottle of water or milk ready to help the little ones pop their ears. The elevation changes can be very uncomfortable for the babies otherwise.

Another tip: our aircraft (Airbus A380) did have changing tables in the aircraft lavatories. Very useful for an emergency diaper change.

Getting Around The Island

We found a great deal for Hertz Rental Car booked through AAA auto club. It came out to around $35/day. This allowed us to rent a mini van to comfortably carry the 6 of us and all our gear around the island. In 90 degree heat, the kids relied on the van’s air conditioning for comfortable naps.

Resupplying on Maui Island


Maui’s Costco warehouse is very close to the airport, making it a great stop right after arrival to the island, and a great stop for gifts and gas before heading back home.

Costco gas is around $.60 less than gas stations. We were paying $2.89/gallon while other gas stations were charging $3.50+/gallon.


Target is a great store  for odds and ends you forgot to bring from home. We went to target to find laundry detergent and baby formula.

Quick tip: check the online price of your items. If it’s less than what is written on the shelf, the cashier will honor the online price.

Safeway Supermarket

This store is convenient if you are staying in Lahaina/Kalapani area. We made a few Safeway trips to buy yogurt for the kids and meat for all of us.

There is no two day free shipping to Maui for Amazon Prime members. Expect packages to take around 1-week to arrive. I recommend you contact your AirBnb host to ask if they can hold packages for you, in case they arrive early. From Amazon, we shipped a box of diapers to the first place we stayed, so we didn’t have to carry a load of diapers on the plane.

Where To Stay

For finding places to stay on Maui, we relied solely on AirBnb, and VRBO/HomeAway searching. We contacted our hosts in advance to make sure it was okay to bring infants. Our generous hosts fielded our barrage of questions and special requests.

For our longest stay, we found an awesome place on VRBO. Then we discovered the rental companies separate website. The rental company charged the same rate on their own website, without service fees. AirBnb, VRBO, and HomeAway charge a fee with each transaction. By doing a little searching we were able to book without the paying the extra fees.

Pros of staying in a non-resort in Maui (i.e. AirBnb)

At home we rely heavily on our blender and electric water boiler for making food and formula for our twins. All the places we stayed in Maui had these appliances, rice cooker, microwave, laundry machines, dish washer, wifi, and more. We were able to very comfortably live and not deviate much from our normal routines.

Icing on the cake is we were also paying much less than a resort would cost. Probably around half the nightly rate.

Cons of staying in Maui AirBnb

If you’re not staying at a Maui resort, be prepared to face all kinds of bugs, geckos, spiders, etc. We did not feel very comfortable letting the kids play on the floor in some places where bugs were a problem. Even in the cleanest place we stayed, we had to be mindful of tiny, invading ants.

We also ran into some equipment issues where our barbecue refused to start, or wifi randomly dying. These were minor problems we quickly worked around.

Getting Home

The day we traveled home was a very long day. Everything went well. We made it home safe without losing any of our belongings along the way. We met a very kind Lyft driver who helped us load all of our stuff into her Plymouth Montana mini van, and this time we managed to fit everything in one vehicle. Overall, I think the trip went well, because we are already planning the next one.

Lessons Learned the Hard Way

  • Airlines do not care about your stuff. It’s worth paying a little bit extra for a bag to protect your stroller, car seats, and other gear.
  • Use a packing list for EVERYTHING and double check it. This should help you not do what we did, leave baby food behind.
  • Spend a little bit extra time to pack more into your checked bags. Use the whole 50 lbs. quota if you can. This will lighten your carry-on load to ease boarding and deplaning.

I sincerely hope all this information helps you. There should be no excuse to not travel with twins. Onward!

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