How to Have 5 Easy Days In Maui With Young Kids

How to Have 5 Easy Days In Maui With Young Kids

Traveling with a 5-year-old and a 3-year-old can be challenging. But traveling is a bucket-filler for my husband and me. So, we figure out how to make it work with the kids. Last month we were able to get away for a quick 5-day trip to Maui with our two boys–and it was awesome.

We chose Maui for a few reasons

  1. In December, the weather is typically warmer than anywhere else in the US
  2. We can take a direct flight from our town to Hawaii, so air travel is easy
  3. We love the relaxed vibes we get when visiting Hawaii

Here is a little rundown of our trip and how we made the most of 5 days in Maui. Are you looking to book a trip to Maui with your kiddos? Check out these ideas where to stay, things to do, and what to eat. 

One quick note: we traveled without car seats this trip, which was terrific. We hired a driver to pick us up from the airport and take us to our resort, which was in a very walkable area. So, we didn’t need to rent a car, which saved us money. If you’re looking for a trip to drive around and explore, I recommend renting a car and bringing your car seats and boosters.

Where to Stay

In the past, we’ve stayed at three different resorts in Hawaii: The Sheraton Kaanapali, The Fairmont Kea Lani, and most recently, for this trip, The Westin Maui Resort + Spa Kaanapali. The Westin was by far my favorite place to stay with the kids. Here are the pros and cons of each resort:

westin maui report & spa pictures from overhead from the west
Source: https://www.marriott.com/en-us/hotels/hnmwi-the-westin-maui-resort-and-spa-kaanapali/photos/
Westin Kaanapali

Pros: great kids pool area with a kid-size water slide, close to Whalers village, game room, onsite Luau, fish + bird feeding opportunities onsite, kid-friendly dining options

Cons: hot tubs are for adults only (our kiddos were super bummed about this), and getting chairs by the kids’ pool area was sometimes tough

sheraton maui from overhead drone aspect with ocean included
Source: https://www.marriott.com/en-us/hotels/hnmsi-sheraton-maui-resort-and-spa/photos/
Sheraton Kaanapali

Note, we stayed here years ago before kids, so I can’t speak to the experience of having kiddos. Still, there are things I remember that may be helpful.

Pros: beautiful location, close to Black Rock which is fun for swimming, close to Whalers village, has a mini water slide for kiddos

Cons: no specific kiddie area or a kiddie pool, sprawling grounds

fairmont kea Lani grounds including view of pools and ocean
Source: https://www.fairmont.com/kea-lani-maui/
Fairmont Kea Lani

Pros: large rooms, we had a suite that had a bedroom attached which was lovely, beautiful grounds, kids pool, water slide, our patio had table and chairs which were nice to sit and eat at as a family

Cons: The kids’ pool was shallow, maybe 2 feet, perfect for Bambino but too shallow for Chulengo. It was easier to get reservations at restaurants if we planned ahead. Which we didn’t always do, and scrambled at mealtime. The overall vibe felt more adult-friendly


What to Do

My favorite part about staying in Kaanapali is the walkability. Walking the beach path and along the golf course or exploring local shopping and dining areas was easy.

three photos: first photo kid playing next to turtle toy, a climbing structure in the second photo. and the third photo a picture of Whalers village shops
Whalers Village

We were near Whalers Village, a gold mine for keeping our kiddos entertained when they needed breaks from the pool. A climbing area with a splash pad kept our kiddos entertained for a good hour. We could sit back in some comfy chairs and let them play. We also explored the Discovery Center, which was perfect for a rainy day. They had a kids’ station with ocean-themed toys and crafts. 

The ABC store at Whalers Village was the perfect spot to stop and grab snacks, souvenirs, and toys needed throughout our stay. The boys loved roaming the aisles, looking at all the different items. We picked up some Hawaiian snacks and grabbed our Christmas ornament to put on the tree this year. 

Whalers Village also has a regular movie night and classes, like lei making and coconut weaving. We look forward to enjoying these fun activities the next time we come to Maui.

two people jumping off black rock in maui
Black Rock

Black Rock is located at the Sheraton Kaanapali, and it’s a great little spot to set up and enjoy a beach day. There’s a shaded tree area in the back, which we wanted for a bit of relief from the sun. The boys enjoyed building sand castles near the water too. Something about the Maui sand is so soft and soothing, making playing in the sand so fun.

There’s also a little shaved ice shop nearby at the Sheraton to get a cool treat mid-day. My husband and I took turns snorkeling in the water, which was relaxing. We saw a ton of fish and a few sea turtles. Some folks jump off Black Rock. While it’s not something I would have the guts to do, it’s entertaining to watch.

fire dance on a stage with red lights and palm trees in background
Wailele Luau

We bought tickets to this Luau before we chose to stay at the Westin, so we were lucky that it happened to be on site. While that was a great perk, this Luau would be worth the drive from another location. I was a bit nervous about taking a 3-year-old and a 5-year-old to the Luau, but we all enjoyed it very much.

The boys tried (and enjoyed) some traditional Hawaiian food, which is a big deal for two picky eaters. Local vendors were set up ahead of time to explore different Hawaiian art and gifts. The entertainment was great – it kept our kids entertained for two hours. There was an open bar with a server for those who wanted to partake. The whole experience was fantastic and memorable.

green trolley in front of a hotel-like entrance drop off
Trolley

There’s a trolley that drives around Kaanapali–FOR FREE! If you have young kiddos, you know this is a special treat for all. I remember when we visited Yosemite; Chulengo loved riding the shuttle bus from the lodge. So, it was no surprise this was a big hit also. We took the trolley to different resorts and shopping areas when it was raining, making a rainy day more enjoyable for the whole family. But this would have been something we would have done on a sunny day, too; the boys love it that much.

shallow beach with reef in background
Baby Beach

While we didn’t make it to Baby Beach due to our last day being rainy– it came highly recommended by some friends we made at the hotel. I look forward to checking this out on our next trip. It’s the perfect beach to take young kiddos as an exposed stretch of reef protects the water, allowing everyone to explore the ocean more safely. The water is more shallow, and there aren’t any waves coming onto the beach because of the reef—a couple of downsides: no public bathroom and no shade. So we would be prepared for this to be a half-day morning trip if someone needed to use the bathroom or it got too hot.

two small kids feeding koi fish and flamingos
Kid-Friendly Activities at the Westin

While the kids’ pool area was the main attraction, we made several stops around the resort to entertain the kiddos.

The Game Room
We spent a few hours in the game room on a rainy day. They had a variety of activities that appealed to Bambino and Chulengo: a basketball net, board games, foosball, arcade games, a play bowling set, a Wii, card games, and shuffleboard. While it got a little busy during the rainy day, it was enough activity to keep the boys engaged and happy.

Feeding the Fish + Flamingos
There’s a beautiful elevated walkway past the lobby, where you will find flamingos and koi fish. Each morning, the boys were able to feed them, which was a unique experience for them.

Tropical Birds
Three tropical birds live along the route to the kid’s pool. The bird-keeper would take the birds out for photo opportunities in the afternoon. We popped over each day to visit with the birds.


three pictures: 1st ahi tuna nachos, 2nd steak and lobster, and third mahi mahi with crab on top

Where to Eat

Hula Grill

Hula Grill was by far my favorite restaurant. The menu was great, the kids’ meal options were delicious, and the service was top-notch. One night I had the crab-topped macadamia nut curated Mahi Mahi. Another night my husband and I shared an Ohana plate with steak and lobster. Both meals were spectacular. The POG slushy was a hit with the kids, and we all enjoyed the original hula pie.

Leilani’s On The Beach

Leilani’s was another spot we hit up in Whalers Village. Outside seating is first come, first serve, which was good and bad. Good because we could grab a table if we saw someone getting up, but bad if we had to linger around awkwardly waiting for folks to get up. I had the poke bowl that night. And my husband had fish and chips. The kids had their go-to pasta and chicken and enjoyed it too. The best part about this restaurant is the view–a fantastic opportunity to catch the sunset.

Joey’s Kitchen

We checked out Joey’s Kitchen for breakfast one morning. It was a great little eatery in the food court in Whalers Village, where we ordered french toast for the kids. Still, we had to call it “Hawaiian pancakes” because life with picky eaters can be challenging, and that seemed to make it more appealing to them. My husband and I shared the Loco Moco, which filled us up.

Westin Restaurants

For simplicity, we enjoyed the restaurants at the Westin too. The Mahele Market & Eatery is a great “to-go” spot. My favorites were the acai bowl, the breakfast eggs + sausage bowl, and the breakfast pizza. There were also drinks and snacks available for purchase that we picked up a few times during the day.

The pool had excellent lunch service too. We ordered lunch for the kids there a few times so they could keep playing at the pool. The nachos my husband and I had were good.

Waicoco was another restaurant we visited. Once for takeout at breakfast and another time for dinner. I ordered the pineapple + bacon fried rice for breakfast, and the boys loved the french toast. For dinner, I had fresh fish, which was Ahi, and it was so delicious. The boys each had a burger that they inhaled–always a win!


Overall our trip to Maui was spectacular. The boys typically travel well, but there are always bumps along the way. Trying to time when they are hungry or tired can be tricky, especially with a time change. The most important thing for us while traveling with young kids on this trip was not to overschedule, be spontaneous, and let the boys lead at times.

If we spent more time building sand castles than we did at the pool one day, that would be great. Sure, if they wanted to order food and eat in the hotel room. Suppose they wanted to spend extra time painting at the Discovery Center, sure thing. We knew that the more fun they had, the more fun we had.

I hope your next trip to Maui is as exciting, fun, and enjoyable as our last trip.



14 thoughts on “How to Have 5 Easy Days In Maui With Young Kids”

  • Too bad your last day was rainy and you could not go to the beach but what a satisfying trip you had overall. I will try and let the kids lead our next trips too.

  • Sounds like an amazing place to visit and stay whether as a family with young children or as a couple, it is lovely seeing how you can visit places with younger children and they are catered for

    • Agree, Samantha. Having been there before kids, it was just as great with kids this time. So thankful for this little getaway.

  • I have never been to Hawaii before. It looks so beautiful and is definitely somewhere I would love to take the kids to. Maui looks like it has so much going for it.

  • The The Westin Maui Resort + Spa Kaanapali really looks fab. Even without specific kid things, there is tons for kids to do around the area. That free trolly looks like a life saver!!

    • Yes! We were shocked by how easy it was to keep the kiddos entertained. The free trolley was the cherry on top for sure.

  • Wow! My daughter (10 years old) really wants to visit Hawaii. It looks so beautiful and that baby beach is such a fab tip to keep hold of. I’m keeping my fingers crossed that we will eventually get to go, as it looks too stunning to miss.

  • oh wow! I would love to stay there for a few weeks, I’ve never been to Maui, the food, scenery, activities…Just amazing.

    • I could stay there forever… everything is just the perfect little escape from the real world.

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