72 Hours in Hawaii-Squeezing Every Bit of Family Fun out of Maui and Oahu

Hawaii with kids

Planning a trip to Hawaii with kids can be an overwhelming task. There are plenty of “must-see” attractions, and many people feel like they “must do” them all because Hawaii seems like a once-in-a-lifetime trip.

So, unless you have an extended stay, how do you get the most bang for your buck? Read on to find out how we squeezed a ton of fun into just 72 hours, and how we plan to leverage our points to get back there someday soon.

Waikiki Surfboards

Waikiki Surfboards

Now, let me begin by saying that doing Hawaii in less than a week is not ideal, and given the choice, we would have spent a longer time. However, school schedules dictate our travel, like I’m sure they do for many of you. If you are short on time, you can still have a great time in Hawaii and see a ton of cool things. When we were planning our trip, it sounded like it would just be frantic and exhausting, but it really didn’t feel that way while we were there.

A quick note: this post covers Maui and Oahu, but we also visited two National Parks on this trip which took us to the Big Island as well. We wrote about that epic adventure in another post here.

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A Quick Visit to Maui – Things to do in Maui with Kids

Because of the five hour time difference, we were able to arrive in Maui in the early afternoon. We took a beautiful scenic drive to our hotel (seriously, could this place be any more picturesque?), and then it was time to locate some food.

The amazing view from our balcony at the Hyatt Regency Maui Resort and Spa

The amazing view from our balcony at the Hyatt Regency Maui Resort and Spa

Lahaina Maui had a relaxed, low-key vibe, and once we got off the highway, we easily found a little fish market, called what else but The Fish Market, that served up some tasty delights.

My main agenda was finding some coconut shrimp, and this place had the best I’ve ever tasted. (They also had some non-fish items for the pickier members of the family…may we recommend the pork tacos?) If you have an extended stay in this part of Maui, you might consider splurging on dinner at Roy’s. That will be on our to-do list the next time we visit.

Exploring the Local Shops

After our late lunch, we had time to explore some of the shopping districts. We visited Outlets of Maui which is where you’ll find the Hard Rock Cafe overlooking the ocean. They have several other interesting local shops, as well as some department store chains. Be sure to stop by Hilo Hattie’s for some Dole Whip and Hawaii souvenirs.

Hard Rock Cafe Maui - Visiting Maui with kids

Hard Rock Cafe Maui

Enjoying the Legendary Maui Sunsets

We spent the rest of our one evening in Maui at our resort, playing on the beach and in the gorgeous pools.

Best things to do in Maui with kids - swimming!

Hyatt Regency Maui Pool Complex

We definitely want to return to this Hyatt for a more extended stay. With several pools, kids’ areas, a water slide, beach access, outdoor dining, and access to the Vacation Club’s pools, there is plenty to keep the entire family happy for several days. But, for us, we had an early start to the next day, and some National Parks to see, so we had to call it a night.

Definitely take in the susnset on Maui with kids

Sunset at the Hyatt Regency Maui

Read about our trip up to Haleakalā National Park here.

The Hyatt Regency Maui is incredible. Check here for the latest prices.

Oahu – More Than Just Beaches and Surfers

Our final two nights in Hawaii were spent on Oahu, and even though there is so much more to this island than beaches and surfers, we really enjoyed those aspects of it as well. After our epic day of National Parks and island hopping, we felt that it would be wise to schedule a day of down time and much needed relaxation.

Duke Kahanamoku welcomes you to Waikiki Beach

Duke Kahanamoku welcomes you to Waikiki Beach

Waikiki Beach

Oahu is home to the famous Waikiki Beach, and it is easy to see why vacationers flock to this spot. With its soft sand and beautiful warm water, you can be happy just sitting and building sand castles, or you can take a surf lesson if you want. There are limitless activities on Waikiki Beach including paddleboarding, surfing, and snorkeling. We even saw a party cruise on a pirate ship sail past.

Surfboard rentals at Waikiki Beach Oahu

Surfboard rentals at Waikiki Beach Oahu

We chose to be lazy and enjoy the sun and the waves. The hotel provided us with beach towels and chairs, which we thought was a nice touch.

I had heard that Waikiki beach was simply too crowded to be relaxing, but in October, the crowds weren’t too bad at all. We spent our afternoon exploring the town and found that Waikiki Beach is home to some upscale shopping and dining, but there are plenty of souvenir shops where you can buy “Aloha” shirts for the whole family, even the dog. Waikiki Beach should definitely be on your list of things to do in Oahu with kids.

We stayed right across the street from Waikiki Beach at the Hyatt Regency Waikiki, and it was so great! Check here for the latest prices.

Outrigger Canoe at Waikiki Beach

Outrigger Canoe at Waikiki Beach

Out and About in Honolulu

My favorite place to explore was about a block away from the beach though. A quick Google search told us where to find Marukame Udon, a Japanese noodle restaurant for lunch (pro tip – Asian food in Hawaii is the real deal, and this place was amazing!). On our way to the restaurant, we wandered through a marketplace full of souvenirs. It was the kind of cram-packed market where bargaining with the vendors is encouraged, so that was a fun experience for the kids.

Shave Ice – Don’t Call It a Sno-Cone

One of the most delicious must-have Hawaiian treats has to be shave ice. This wonderful dessert has a long and proud history in Hawaii, and one of the best places to get it on Oahu is Uncle Clay’s House of Pure Aloha. You are in for a treat when you visit Uncle Clay’s, and I’m not just talking about the shave ice. But, I’m pretty sure this stuff is made of sunshine and rainbows, so we’ll start there.

Uncle Clays House of Pure Aloha - Honolulu Hawaii

Aloha in a bowl at Uncle Clays

Hawaii with kids must include Uncle Clays House of Pure Aloha!

One of the fine creations at Uncle Clays

We love us some tasty sno-cones at home, but I’m not sure if I can ever eat one again after experiencing a true Hawaiian shave ice.

At Uncle Clay’s, they use fresh local ingredients to flavor their ice rather than the sickly sweet corn syrup stuff you’re used to. And, for those who want some extra tasty goodness, you can have your shave ice atop a bed of fresh ice cream. They offer flavor combinations that you can choose yourself, but we recommend trying one of their expert creations.

The second treat at Uncle Clay’s came as we were about to leave. We had the pleasure of meeting Uncle Clay himself, and a kinder, more welcoming person you will never meet. It is easy to see why his shave ice is award winning. He pours so much love into his business and his customers. You will leave feeling like family, or Ohana.

As we got back into the car with full bellies and hearts, I was ready to turn around and have another round. Put Uncle Clay’s on your Oahu to-do list, and tell him his Ohana from Oklahoma sent you.

Uncle Clay - Uncle Clays House of Pure Aloha - Honolulu Hawaii

Andrew learning about Aloha and Ohana up close.

Pearl Harbor, Dole Plantation, and More

Pearl Harbor

Our final day on Oahu was another one that I worried would feel frantic, but I was pleasantly surprised that it did not. We started our day early with a trip to Pearl Harbor and the World War II Valor in the Pacific National Monument. They give out a limited number of tickets each day (free of charge), so we got there as early as possible to ensure that we could fit everything into our schedule for the day.

You can expect to spend a minimum of 1 1/2 hours at Pearl Harbor, but there are both free and paid museums, and a paid tour of the USS Bowfin submarine that will add to your experience. We skipped the paid exhibits and still had a full morning.

USS Bowfin at Pearl Harbor Oahu

USS Bowfin at Pearl Harbor Oahu

Our experience at Pearl Harbor was wonderful. As one of my friends put it, the experience is really “indescribable.” It is hard to put into words what this living monument is like and how we felt during our visit. They have done an excellent job of presenting the history on both sides of the war, honoring the Americans who lost their lives in the attack, and honoring those heroes who survived, as well.

Pearl Harbor Museum

Pearl Harbor Museum

We left understanding more about why the attack happened, and how the American people rallied to rebuild the fleet. It was a somber place, yet beautiful at the same time. Andrew said that our visit to Pearl Harbor was his favorite part of our entire trip, and we all learned just a little bit more about our nation’s history.

USS Arizona Memorial - World War II Valor in the Pacific National Monument

USS Arizona Memorial – World War II Valor in the Pacific National Monument

If you want to read more about our adventures this year visiting the U.S. National Parks, check out these other posts:

Dole Plantation

After Pearl Harbor, we headed to the Dole Plantation, which is just a short drive away. Again, what a learning experience! We learned about the history of Dole and the pineapple, as well as some tips for cutting and serving this delicious fruit. The Dole Plantation has a narrated train ride, a garden walk, and a world record pineapple maze. You can do as much or as little as you want, and we did it all.

Disclaimer: We were provided admission by Dole Plantation for 2 of us, and we purchased tickets for the other 2. We loved it, and so did the kids!


First, the train ride takes you through the pineapple fields, and the narrator tells how this crop came to be. It is amazing how quickly the company and the demand for this product grew. You will also learn about other tropical crops grown at the Dole Plantation.

Pineapple fields at the Dole Plantation - Wahiawa, Hawaii

Pineapple fields at the Dole Plantation – Wahiawa, Hawaii

Next, we attempted the Pineapple Maze. On your ticket, you will see that there are 8 checkpoints with symbols that you will collect. We were told that it takes an average of 45 minutes to get through the maze, and I went in thinking “we got this.”

Oh man, was I wrong.

Fun though the maze is, we only found half of the symbols in 35 minutes.

Pineapple Maze - Dole Plantation


Maybe we weren’t trying hard enough, maybe we were overconfident, or maybe we had too many little “leaders,” but whatever the case, we failed miserably. When you go, you should prepare yourself for a real challenge!

Dole Whip (the real reason we visited Hawaii)

After 35 minutes in the maze, the warm sun and the siren call of Dole Whip did me in. Maybe that was our key mistake…we should have taken sustenance into the maze with us. Let me just say to you right now that leaving the Dole Plantation without sampling the Dole Whip is a sin against nature. You can have it in a float with pineapple juice, on a cone, in a cup, sprinkled with fresh pineapple, or in the form of a gigantic sundae. Whichever you choose, you’re in for a treat.

Dole Whip

Dole Whip Cup

Dole Whip Float - Dole Plantation

Dole Whip Float

Dole Whip Cone - Dole Plantation

Dole Whip Cone






It’s a trifecta of yumminess!

The Disney fanatics know what I’m talking about. And, this may be the sadness of the maze failure talking, so don’t take offense, Disney, but I think the Dole Whip is better in Hawaii. I needed a pick-me-up, and this stuff is totally worth the long flight. If you are an unfortunate person who has never heard of Dole Whip, the quick explanation is that it is pineapple flavored soft serve, but that description does not do it justice.

A wonderful way to enjoy your Dole Whip (and perhaps a more relaxing way than the maze), is to take it with you on a walk through the gorgeous garden.

Dole Plantation Garden Tour

Dole Plantation Garden Tour

Here you will find native plants, and you will learn about the different types of bromeliads that are related to pineapples. With clean paved paths, cool shady benches, and beautiful foliage, the garden is a relaxing way to spend your time at the Dole Plantation.

Fiery Colors in the Dole Plantation Garden

Fiery colors in the Dole Plantation Garden

Enjoying the beautiful views in the Dole Plantation gardens

Enjoying the beautiful views in the Dole Plantation gardens

Hibiscus pitstop at the Dole Plantation Garden

Hibiscus pit-stop at the Dole Plantation Garden

Garden waterfall at the Dole Plantation

Garden waterfall at the Dole Plantation

Before leaving, you should stop by the gift shop. This isn’t your average touristy gift shop. There are pineapple flavored treats, pineapple dyed shirts, and other pineapple themed souvenirs, but I really liked the section of the gift shop that featured various local artisans and vendors. If you’re looking for great Christmas gifts, this is your stop.

As for Cadence, the Dole Plantation was her favorite thing to do in Hawaii. All kidding aside, it was the maze that she loved the most, and the rest of us thought it was pretty cool, too. Even if you just want to stop in for some shopping and Dole Whip, put the Dole Plantation on your list of things to do in Oahu.

Dole Plantation is a great way to visit Hawaii with kids!

Dole Plantation is a winner!

North Shore and the Bonzai Pipeline

After the Dole Plantation, we had plenty of time to continue exploring Oahu before our flight home. We decided to take a drive to the North Shore to check out the famous waves.

North Shore - Oahu Hawaii

North Shore – Oahu Hawaii

Just minutes away from the Dole Plantation on King Kamehameha Highway, the North Shore is a stunning stretch of beaches that feature sand, rocks, tide pools, and enormous waves. We explored some of the tide pools and just marveled at the surfers.

North Shore - Oahu Hawaii

Exploring the tidal pools in North Shore – Oahu Hawaii

Oahu North Shore and the Bonzai Pipeline

Oahu North Shore and the Bonzai Pipeline

Other North Shore Activities

The North Shore is full of things to do. In addition to the water sports, there is the Polynesian Cultural Center, exploring the breathtaking beauty of the Waimea Valley, and turtle watching at Laniakea Beach. We loved the laid back vibe, and with endless food choices, you won’t get bored. We found a little food truck park and enjoyed some fish tacos and shave ice. Don’t forget about Matsumoto’s, maybe the most famous shave ice joint of them all.

All Good Things Must Come to an End…

After dinner, it was time to drive back to the airport. It was an amazing day (and an amazing trip overall), but we were worn out! Although our time in Hawaii was too short, we’ll be back. With so much to do and great weather, how could we not?

Hopefully we’ve given you a taste of what to do when your family is ready to plan your trip to Hawaii. We know you’ll love it!

Pin this post to your favorite Pinterest board!Check out all the family adventures you can have in Maui and Oahu in just 72 hours! We squeezed every bit of fun out of it and so can you. It was awesome!

Putting it Together

Trip Planning

Lonely Planet Discover Honolulu, Waikiki & Oahu – This is the guide we used to research and map out our short list. As with all Lonely Planet guides, this one is excellent.


We used points to fly United from DFW-OGG with connections in San Francisco and Honolulu. We paid cash for the intra-island flights on Hawaiian Airlines. We ended up flying OGG (Maui)-ITO, ITO-HNL, and then HNL-SFO-DFW.

Hawaii can be easy to get to if you use points. To learn how to leverage points and miles for your family travels, head over to our landing page and sign up! We made a free 13-page eBook that will get you started!


We used a combination on points and cash to book rooms at the Hyatt Regency Maui resort and the Hyatt Regency Waikiki Beach on Oahu. Both resorts were fabulous!

Click Here to compare other hotels near Waikiki beach.

Car Rental

For each of our stops, we rented a car (3 total) and this is what you’ll most likely want to do if you want to do any exploring of the National Parks or North Shore in Oahu. It’s the most convenient way to get around.

There are so many things to do in Hawaii with kids! Have you been? What were your favorite things to do there?