It’s been a rather long time since we’ve gone on a vacation, and we thought, “Hey, why not throw in a flight for our first vacation with two small children? I love chaos!” (said no parent ever). Don’t get me wrong – I feel extremely grateful and fortunate for the opportunity to go to Maui, one of my favorite places on the planet. But the idea of 1) flying and 2) flying into another time zone with two children under the age of five is enough cause for a minor panic attack.

I’m happy to report we all survived and enjoyed (well, at least three of the four of us) the trip! KJ, our 11.5 month old, struggled the most with the time change. Hawaii is three hours behind our current time zone, and so he never really adjusted to the change, which also means he had the easiest adjustment back at home.

View from our room at the Fairmont Kea Lani Resort

LODGING: Now when we travel as a family, we usually book an apartment or condo through VRBO or AirBnB.  You can find some really great budget and family friendly places to stay, which most often end up being cheaper than staying in a hotel room. With the two little ones, we enjoy having separate rooms and a kitchen to have the option of eating in for breakfast and/or lunches. A number of complexes, such as Wailea Ekahi Village and Wailea Elua, even have direct beach access!

We decided to book our trip for 6 nights, mainly to give ourselves and the kids enough time to adjust, and so that we wouldn’t feel the need to pack in our schedule.

My husband and I had been to Maui a couple of times BC (before children), but not in the last seven years. We have only ever stayed in Wailea/Kihei area, which is on the southwest side of the island. I’ve heard that Kaanapali and Kapalua on the northwest side are great places to stay (especially if you want to golf), and Lahaina, which is on the west side, is also great if you are looking for more night life.


We booked our first 4 nights through VRBO and found a 2 bedroom condo at the Grand Champions in Wailea. This is a great place to stay for families, and the beach is only a couple of minutes away by car. There is also a swimming pool on site. We would have preferred to stay in Ekahi or Elua for the direct beach access, but we booked our trip last minute and had limited options.

Since we saved money by going through VRBO, we decided to stay our last two nights at the Fairmont Kea Lani Resort. The Fairmont Kea Lani has a number of gorgeous swimming pools (one featuring a giant water slide, and one adults only pool), direct access to a private beach, a number of excellent restaurants, a spa, and is also an all-suite hotel (which is also great for families).

Maui Ocean Center

FLIGHTS: As a first-time mom, when we would fly with Aliya, I would always select a time that coincided with her nap schedule. We soon found out that she was incredibly over-stimulated since everything on the plane was new, and she would not sleep.  This time around, I decided any flight that was 1) not a red-eye (since I was certain my kids would not sleep) and 2) non-stop would be fine.

Ready to go at LAX

CARRY-ON ITEMS: In addition to my regular diaper bag, I brought a small duffel bag as my carry-on item, fully-stocked with diapers/wipes/changing pad, an extra outfit for each child, my baby carrier (Ergo), snacks, toys, loveys, and an iPad (loaded with new Daniel Tiger and My Little Pony episodes).

CAR SEATS:  This was the first time we rented car seats with the car rental company (we went through Budget/Avis). I know parents can be 50/50 on car seat rentals, but I would 100% do this again for the convenience. Renting car seats saved us both time and energy and the airport, and with the extra bodies and luggage we had to haul around, we could use all of the extra time and energy we could get!

ACTIVITIES:  For the actual trip, we decided to keep our plans as loose and open as possible. Our main hopes for the trip were to just spend time altogether as a family, make some memories, eat good food, and enjoy Hawaii’s beautiful landscape.

Ready to hit the beach – 4th of July style

We tried to incorporate time for naps, but the sound of the ocean’s waves were a perfect lullaby for this guy:


And while the beach was great for play and sleep, it wasn’t so much for swimming. At least, not for the kids. They were terrified of the waves, and screamed every time I tried to take them into the water. And so, we improvised and headed to the pool instead:


We also took one day to visit the Maui Ocean Center, which is a great aquarium for little ones. I think this was one of Aliya’s favorite outings. They have an online booking special where you can get a free upgrade to a one-week pass for the price of a regular ticket. Children under three receive free admission.


I have also heard that the Old Lahaina Luau is a wonderful luau for visitors, but there were no openings during our entire stay.  If you want to go to a luau, book your reservation early!

FOOD:  Here is a list of some of our favorite eateries in Maui:

  • Paia Fish Market – For amazing fresh fish tacos
  • Kihei Caffe – Great for breakfast – they have a delicious pork fried rice and offer specialty items like banana macadamia nut pancakes
  • Eskimo Candy – For fresh poke bowls (we had this twice on our trip)
  • Mama’s Fish House – For amazing beach view; this is a bit more up-scale and good for a romantic night out. We weren’t able to make it to Mama’s this trip with our two screamers.
  • Star Noodle – Delicious garlic noodles; Asian fusion food
  • Ululani’s Shave Ice – For dessert – make sure to get the condensed milk “snow cap” for added flavor!
  • Leoda’s Kitchen & Pie Shop – For amazing pies and sandwiches

This was before the noodle throwing and shrieking inside the restaurant.

Upon arrival, we stopped by the Walmart next to the airport to grab some essentials, such as eggs, cereal, milk, toast, and yogurt, and were able to eat a few breakfasts in the condo. There is also a Costco and a Target next to the airport for other necessities.

We made sure to eat our meals early, since for the majority of our trip the kids were still on California time.

At our last dinner in Maui

All in all, we had a wonderful time there, but I think the kids were just as happy to be back home after a week away. Having survived this experience, I’m more confident and am even looking forward to future trips together (especially those within driving distance).

My number one travel tip for traveling with small children is to be flexible!