10 Days in Maui With Kids: Our Complete Family Itinerary

We recently returned from what might be our most epic family vacation ever – 10 days on Maui, Hawaii.

This trip has been a long time coming as I started booking the hotels 13 months out. All of the hotels and flights were paid for with points.

I'm not going to go to any detail about earning points in this blog post, but you can read my guide to getting started traveling on points with your family, and I wrote a more detailed guide to each of the hotels we stayed at and they include specific details on how we paid for them with points.

This was the first really big vacation we have taken with our kids who were 5 ½ and 7 ½ years old at the time of the trip. We planned it for the middle of June while they were on summer break from school.

We planned the trip to stay in three different hotels so we could check out different parts of the island and have a balanced use of hotel points for booking our staff.

A rental car was essential for us being able to get around the island at our own leisure.

The goal of this trip was to have a nice mix of resort time as well as adventures without over-exhausting anyone.

If I did the same trip with just my husband, we would've done it very differently, but we had to keep it realistic to avoid meltdowns and I think it turned out really great.

I'm going to share our day by day itinerary with you and then I'm gonna share what I would have changed if I would do this trip again!

Our Maui Trip At a Glance

We traveled to Maui, Hawaii and spent 10 nights on the island (plus 1 night on the plane on the way home). We travelled in early to mid June, while the kids were on summer break from school.

We flew to Maui on Delta and home on Alaska Air. There is truly no easy way to get to Maui from a small east coast mainland airport. Our travel days were long and rough, which is one reason we wanted to have a nice long stay on the island!

10 Days in Maui With Kids

Here is a look at our day by day itenerary!

Day 1: Arrival in Maui

Our flight arrived in Maui just after 7pm Hawaii time (1am East Coast time). We had checked (a lot of) luggage, and had to wait almost 30 minutes for it to come out.

One thing that made this process go a bit quicker was the boys waited for the luggage while Rory and I went ahead and hopped on the shuttle to the rental car. It took less than 5 minutes to get to it and about 10 minutes to complete the required paperwork for the jeep. Side note- definitely get a jeep in Hawaii!

Then, we drove back to the airport in time to pick up the boys. It was a little frenzied splitting up at this point, but definitely sped up the process and cut down on waiting time for the kids.

We then drove about 40 minutes from the airport to the hotel. We were surprised it was pitch black outside - the sun sets later at home this time of year.

We arrived at the Grand Wailea and drove in through a tunnel of gorgeous trees dripping with white twinkle lights. It's a stunning entry at night!

We checked our car with the valet (no self park available, $75 a day at the time of our stay) and they took all of our bags for us (guests are not allowed to roll a luggage cart themselves).

There was luckily no wait at the check in at this time. We had a kind of complicated reservation because our 4 nights were 4 separate reservations. This is because we used free night credits, each of which have to be stand alone reservations.

Luckily, we had emailed all of the confirmation numbers to the concierge in advance. They cannot merge the reservations, but since we made sure they were all the same room type, they were "linked" so we did not have to check in and out daily.

However, because of this complicated set up, the digital key in my Hilton app did not work correctly. We just used a normal key and it was fine!

Because of our Hilton Gold status (not a super high status with hilton, free with our AmEx card), we were upgraded to an ocean view room. Sean was also very friendly and nice to the check in staff and that might be why we got a corner room with a bit of extended extra space.

We were thankful and thanked him the next day and by name on a feedback form after our trip!

This was a super long travel day, especially with the time change, and we wiped out and slept hard!

Our first full day in Maui we woke up very early – about 5 AM – despite being exhausted. The time change just really goes to your head!

We hung out in the room a little bit until the restaurants downstairs opened up. The Grand Wailea has a buffet breakfast, but it is pricey and my kids are not great at a buffet so we decided to go to the grab and go restaurant instead.

They have bagels and breakfast sandwiches as well as prepackaged food items and smoothies. We somehow spent over $100 on breakfast even though it was just simple grab and go items.

Because of this, Sean decided to go to the grocery store that night. So after the kids went to bed, he went to a nearby grocery store and got breakfast and snack items that we enjoyed the rest of our stay. Highly recommend this or you'll go broke.

After eating, we headed back to the room to put on bathing suits and sunscreen and headed to the pool.

The pools at Grand Wailea are phenomenal. It's worth noting, however, that the waterslides do not open until 10 AM. When you are still on East Coast time in your brain, you have lived a whole day by 10 AM.

We actually rented a cabana for our first day there because I knew we were going to want to just lay around. If you want to rent a cabana at the Grand Wailea, you need to do it way in advance.

You certainly could not rent one the day of because they were all booked up, but also the prices surge charge, so if you book it way an advance, you pay less than you pay day of (if there is availability).

Somebody told us that one of the days we were there the cabanas were going for $1,500. I paid $500 for our cabana for a day which I still feel like was a rip off but I really enjoyed it for this day.

The cabana includes a really nice, fully closed in structure with a fan and lounge bed. There is also a mini fridge and a cabinet to secure your items. You also get two lounge chairs outside of the cabana that are reserved for you if you want to sit in the sun.

Included in the cabana we got a beautiful fruit plate in the morning and then in the afternoon they brought us like a goodie bag of Hawaiian treats like chips and cookies.

We had an ocean view from our cabana and we're pretty close to the little kids pool. That said, my big problem is I like to really watch our kids in the water and I could not see them great from the cabana. So we couldn't actually sit in the cabana while they played, so we took turns as adults.

So that's just something to keep in mind if your kids need really good supervision.

I do not think that the cabana was worth the price but we sure did enjoy it. If you were on a budget, this is not where I would splurge but I figured that we were getting the room for free so it was worth not having to worry about getting a chair or a shade our first day.

I can't talk enough about how fun the pools are at this hotel. It is like a massive lazy river, but instead of a normal lazy river it is a lot of small pools connected by short slides. Plus, there were so sections that had you feeling like you're going through rapids in the jungle. It was so unique and fun.

All of the landscaping is so epically lush and gorgeous. You just really feel like you are in the rainforest. There were also two big slides– one is a tube slide and one is open – that my son really enjoyed.

I go into a lot of details about the pools in my Grand Wailea review so you can read that there, but just know that these were the nicest resort pools we have ever stayed at in our life.

Read my full Grand Wailea review

The Grand Wailea also has a really nice beach. It is directly across the sidewalk from the kids pool and it has nice sand and gentle waves.

I don't think I really understood how nice this beach was until we went to some other places on Maui, but this is a really good beach, especially for it being so convenient to the hotel.

We were able to walk over to the beach and spend just a couple of minutes swimming in the ocean and then come right back to the pools if that's what the kids wanted to do. I loved having the beach right there.

That night I had made an advanced reservation for 5pm at Monkeypod Kitchen, just a 5 minute drive from our hotel in Wailea.

This restaurant was in a strip mall with no view but had great vibes and sort of casual upscale food, with a focus on sustainability and Hawaiian native ingredients.

The problem was that Luke literally fell asleep at the table. He was so tired from the big day in the sun and the time change, he just knocked out. Rory was very sleepy and a bit weepy and it all went sideways.

If I could do it again, I would have planned to do something like send Sean out for a pizza to eat on our balcony night one!

As I mentioned, after the kids went to bed (in their clothes! because we carried them up from the car asleep!) Sean went to a Safeway nearby and grabbed some food items. This was crucial for the rest of our stay at the Grand Wailea.

Day 3: Resort + Luau

Our next morning, we had a few different ideas of things to do around Maui in the Wailea area, but our kids really wanted to go back to the pools.

So we spent the entire day until about 2 o'clock at the pool. The kids had a blast going around and around the slides.

After that, we went up to the room and showered, and the kids watched a little bit of TV while we got ready and did a little bit of work on our laptops.

That night we had tickets to a luau that I researched and found was a great luau to take kids to because it had chicken tenders and mac & cheese. Most luaus have more traditional food (which is great) but we knew our kids wouldn't eat it.

It was a great show, but I did not realize that it was super far from this hotel and actually right next-door to the hotel where we were staying later in this trip. So we drove an hour each direction to the luau. That was obviously a fail and a mistake on my part so do not make the same mistake!

If you are booking excursions and staying at different hotels on Maui, pay very close attention to where they are located because it is not a tiny island and it takes a while to drive from spot to spot.

The luau was called Myths of Maui and it was great. There was beautiful dancing, a buffet dinner, unlimited drinks, and it ended with fire dancers.

We had a fantastic time, but the kids were very tired by the end. I just really wish I had booked this closer to the end of our trip when we were staying at the convenient hotel and were more adjusted to the time change so we could be more alert in the evening.

I will say that we booked VIP tickets to the luau. That got us early entry which meant we got to go to the buffet and drink lines before the massive crowds came in. We also were seated in the front area of the audience and got a slightly nicer lei. I think it was worth the upgrade, if it's in your budget.

Day 4: Molokini Snorkeling

The next morning, we woke up early because we were going snorkeling on the Pride of Maui. I was excited because I love a snorkeling excursion. This one had two stops: one at the Molokini crater and the second at what they called "turtle town."

The boat was great and while there were a lot of people on it, it did not feel overly crowded.

They started us off with breakfast of muffins and fruit, and rode out to the crater. It was so fun to be out on the water and the views were gorgeous.

I did not like that they did a lot of upsells on the boat, such as trying to get you to purchase a scuba class or a wetsuit. That being said, I did get the wetsuit for me and the kids because the water was cold, but I just didn't like the vibes of how they were doing these upsells and you had to Venmo them.

Molokini Crater was really cool to check out, but there were not many fish or very colorful coral. The water was super clear, but otherwise the snorkeling was pretty meh. It was cool though to be able to say you swam in a volcanic crater.

After this stop, we were served a lunch of hamburgers, hot dogs, and chips. They were great and you added your own toppings which was perfect for the picky eaters in our group. Nothing hits quite like a burger at sea!

We then went to Turtle Town - which was just off the coast of our hotel! We laughed to be back at our beach where we had just been swimming the previous day.

The water here was a little more rough and less clear. We technically saw 2 turtles, but they were way at the bottom and not moving, so they mostly looked like rocks.

Overall, being on the boat and in the water was awesome, but don't expect to see a lot while snorkeling. We have done some great snorkeling in the caribbean and the Keys and so this was a bit whomp whomp for that, but the vibes were excellent. They claim it's usually better, but you can't control what Mother Nature gives you.

We then boated back to the dock and soaked in all of the beautiful sites of Maui from the water.

We had noticed a small lighthouse just down from the marina, so we drove over there to take a peek after returning to shore. It.s a super small lighthouse - but great sweeping views of the island!

That day we spent a little time at the pool after snorkeling, but everyone was pretty tired.

We did not have dinner reservations booked and decided to just grab pizza from the hotel grab and go restaurant and eat it in the room. It was just what the kids needed and we went to bed early knowing that the next day we were headed to Hana!

Day 5: Road to Hana

Today was arguably the best day of our trip as we drove the famous Road to Hana. We've heard it's pretty essential to get up and get going pretty early, but unlike most people, we were actually planning to stay in Hana, so it wasn't as big of a deal.

Most people tend to just go out and back in a day, making for a lot of windy driving, especially with young kids. So we wanted to plan to stay in Hana and experience that part of the island. Spoiler- we were very glad we did.

We checked out of the Grand Wailea in the morning and started the drive. We used an app called Shaka Guide that talked through the entire drive and told us history as well as good places to stop.

It started by having us stop in the small town of Pa'ia, which is the last town before you really kick off the Road to Hana. There's a parking area and lots of little shops. There's a great place get sandwiches to go called the Hana Picnic Lunch Company.

They made us great smoothies and sandwiches and offered some good tips for the drive. We ended up stopping here on the way back two days later AND when we went out to go ziplining a week later.

Here's some of our favorite stops on the Road to Hana for our 5 and 7 year olds:

• Twin Falls- you do have to pay for parking here and there are limited spots, but it's a good first adventure for kids.
• Ke'anae Peninsula- specifically stop here for Aunty Sandy's Banana Bread. It's incredible and warm. Get two, then drive down to the end of the road and eat it on the rocks on the ocean.
• Pua’a Ka’a State Wayside and Falls- this is an amazing swimming hole with two different waterfalls. Plus there's bathrooms.
• Coconut Glen's- when you see this small ice cream trailer, stop and get the ube flavored ice cream, trust me.

Our kids handled it great, but we did give them kid's Dramamine just in case. We didn't want to have any problems with that. We also did have all those snacks, which is good because there aren't a ton of places to get food on the Road to Hana.

At the end of the drive, we arrived in Hana and checked into the Hana-Maui Resort. This might be the most deceptively cool hotel we've ever stayed at. It looks like nothing from the front, but that's just the main, one-story building.

After check in, we loaded our bags onto a golf cart and they took us to our room, which turned out to be an actual bungalow house. And not only that, but because of our Hyatt Globalist status, they upgraded us to include both sides of the bungalow.

There were a ton of these houses around in a giant grassy field and we were right next to the pool, which was amazing for the kids. We were also able to walk around the the fitness trail, breakfast and anything else we needed.

This property deserves to be stayed at because it is so calm and relaxing and everything around is beautiful. The staff were all amazing and they served an incredible breakfast too.

Read my full guide on the Hana-Maui Resort with kids!

Day 6: Exploring Hana

The reason we stayed in Hana was so that we could more thoroughly explore some of the biggest attractions in the area at the far end of the road. We started the day going to Black Sand Beach at Waiʻānapanapa State Park. You need a reservation to book a time slot in advance, so make sure you do that.

We got our two hour time slot and showed up right after the allotted time. The hike down to Black Sand Beach is a lot of stairs, so be prepared and have sandals. When you get to the bottom, the black "sand" is very hot.

Our other big adventure for the day was driving to Wailua Falls. Wailua Falls is one of the tallest waterfalls in Hawaii and is definitely worth seeing.

We wanted to do the Seven Sacred Pools and the Pipiwai Trail, both in Haleakala National Park, but our kids were done and just couldn't handle the idea of another two hours outside late in the afternoon.

We headed back to the resort and went to the pool again for a little while and then got some more food truck food to bring back to the room for the evening. We loved the slow pace of this day while getting to really enjoy some of the big parts of Hana.

Day 7: Back to Ka'anapali

We ate the included breakfast at the hotel again, then packed up our stuff and drove over to the Hasegawa General Store to pick up some post cards to mail from Hawaii. It's a family run store that has been around for like 100 years and has literally everything and nothing at the same time.

Then we drove back the Road to Hana in reverse, stopping at a couple of places again that were quick and pretty, but also stopping at the Garden of Eden park that we had skipped on the way in.

The Garden of Eden is a really nice (paid) park to go to with the kids. It has lots of interlapping trails where you can see amazing plants and trees as well as views and wildlife. We had a family of peacocks walk right up to our car when we got out!

We then drove out and stopped again at Pa'ia town on the way out and got some souvenirs and ice cream to take a break from the car. The drive from Hana to the Hyatt Regency is pretty long because the Hyatt is in Lahaina, on the far west side of the island.

Specifically there are several macaws, parrots, and, best of all, penguins. They have a whole group of penguins that they do an informative show with every day. Not something you'd expect to see in Hawaii!

It was late in the day and we were pretty wiped, but we checked out the pools before grabbing dinner and heading to bed.

Read my full guide on the Hyatt Regency Resort with kids!

Day 8: Resort Day

This morning we decided to wake up and spend the full day relaxing at the resort.

I booked a cabana - in advance - to relax in. While the cabana was nice to have, so we had guaranteed shaded seats, it was not as deluxe as what we got at the Grand Wailea. It was basically just a 2 seater chair with a cover.

The cabana was also by the main pool, which was fine, but our kids really wanted to spend a lot of time in the kids pool. Because the pools were far apart and not visible from one another, it meant we really didn't sit in our cabana all that much.

One great thing about this Hyatt resort is that they have a lot of free family-oriented activities - lei making, bracelet making, hula lessons, and more. However, you have to pre-book a slot at them. There were 0 same-day slots available for anything.

So, this day I was able to book a lot of the fun activities that my kids were seeing happening, but we were not able to actually do them. That led to our next day becoming a resort day, too, but I will get to that tomorrow!

Anyways, we spent this day going back and forth between the 3 pools at the Hyatt. The main pool was fine, but a little too deep for Rory.

The kids pool was a huge hit for the kids - but very crowded and nothing for adults to do except perch on a ledge and try not to get splashed by kids.

The pool at the Vacation Club next door was actually my favorite - with a great balance of waterfall features, a manageable depth (about 48" throughout, give or take), and not too crowded.

Unfortunately, we were unable to visit the beach at the Hyatt as it was closed off. The tide was all the way up and there was no sand in front of the hotel. You were able to go 2 hotels down and access the beach there, where it was less eroded, but we found the water a bit rough for the kids.

In talking to others who have been to the resort, I think that the tide was abnormally high during our visit, but that was our experience.

In general, the hotel needs to do something soon or the hotel property is going to get washed away. The beach is totally gone and the waves literally splash over the temporary retaining wall onto the pool deck, making for dangerous and dirty conditions along the stretch between the two pools.

If they aren't careful, the property is going to erode soon, so be sure to keep up with conditions before you go.

That night we drove down to Whaler's Village, which is a shopping center with lots of restaurants and activities as well. Fun fact we didn't realize- you absolutely should not drive to Whaler's Village from the Hyatt Regency.

It's about a 15 minute walk and we spent more time getting our car from the valet, driving, trying to find a spot in the parking deck at the village and walking down than it would have taken to just walk.

Day 9: Resort Day

As I mentioned, we ended up spending this day as a resort day at the Hyatt Regency as well. At this point, we were 9 days into a very big trip, so our kids were pretty tired of being in the car all the time and wanted to do some things at the hotel.

We did the lei making and bracelet making classes and our daughter did the mermaid class at the pool. The mermaid class we so good for her. She got to pick out a mermaid tail and accessories before getting a full photoshoot by the foliage. Then the instructor took her into the water and did a full private lesson making her feel like a real mermaid.

That night after dinner, Sean and Luke walked back to Whaler's Village because Luke had seen that they had an escape room place and has always wanted to try one. The two of them did the escape room and escaped with less than two minutes left! They had a blast even with it being fairly small.

Day 10: Ziplining

On our last full day in Maui, our big activity was going ziplining. Here's another example of not having paid attention to where things were before booking because this zipline place was back past Pa'ia on the Road to Hana. We absolutely should have have driven an hour back for this day.

However, the ziplining itself was awesome. We were nervous because Rory usually gives up on these things before starting because it's new. But today, she surprised us all and did everything!

The zipline park was a series of 7 lines between different platforms criss crossing their property. Some were taller and bigger than others and the kids loved it. There is some waiting around, but once the kids were literally locked in, they were all about it.

It was a long drive, but the activity was absolutely worth it. Then we drove back, stopped in Pa'ia once again (we really liked this little town), and went back to the hotel for a final afternoon of relaxing.

Day 11: Near the Airport + Flying Home

On our final day in Maui, we got a late checkout at the hotel and spent the morning at the pool in order to limit our time we would have to kill later. Our flight was a redeye, not leaving until after 9:00 pm, so we had a long day.

After the pool and showers and packing, we went to the Maui Ocean Center and explored. We have an amazing aquarium in our hometown, so this one was a little underwhelming, but also I was expecting to see more animals that I'd consider to be native to the Hawaiian area. But this was a good (air conditioned) activity to spend the afternoon at.

Then we drove to the other end of the parking lot and went to the Maui Golf and Sports Park, which has putt putt, go karts and some other things. We played a round of putt putt and realized that when you pay, you're getting access for the whole day. However, at that point, they were about to close and we needed to leave anyways.

We didn't feel like doing anything fancy for dinner and didn't want to end up with any time issues, so we went to Chick-fil-A for dinner near the airport. Then we filled up the car and headed inside.

There's nothing to do waiting in the Maui airport, and it doesn't take long to get through security and to your gate, so don't plan to get there too early.

Top Tips for a Successful Trip

Here are some of our best advice for a family trip to Maui:

• Pack floats + a pump for the kids in the pools - most the pools were over Rory's head so a float was clutch and we gave them to other kids when we left.
• If you are planning to rent a Jeep Wrangler (which we did and is very common in Maui), make sure you don't pack too many bags. There's simply not a lot of trunk space.
• Plan to get groceries at some point so you have familiar foods even if just snacks + drinks. It's a great way to save a little money, too!
• In my mind, Hana is a must-do. I would cut a beachside resort before I would cut this portion of the trip. It would also work at the end of the trip, we met a family who was driving back from Hana > catching an evening flight home that same day.
• Make sure the activities you book are near your hotel and plan around those days. Don't criss cross the island over and over again.
• Book more than one hotel and spend time in different areas. There's more than one type of activity on Maui, so try them all.
• Spend at least one day doing nothing. If your trip is longer, make it two. There's a lot to do on Maui, but if you try to have big activities and lots of driving every day, you and your kids will get burned out.
• Have a good list of activities planned for your last day if you have a night flight home. Don't spend the whole last day of your vacation doing nothing and being miserable.

Things We'd Change

We LOVED the trip, but here's what I would change if we did it again:

• I would stay at the Hyatt first and end at the Grand Wailea because I think the Hyatt would have felt nicer if we hadn't just been at the super luxurious Grand Wailea!
• Pay very close attention to where excursions are located and if you are staying at multiple hotels, book when they are nearby.
• Book later evenings like restaurants and luaus later in your trip when you've had time to get used to the time change.
• I personally would have liked to do some off-shore snorkeling, but after seeing how our kids did snorkeling on the excursion (refusing to put their heads under, clinging onto us, etc) we decided not to pursue it. We did however bring our own snorkels and I wish we could have done more.

Related Guides

• Grand Wailea Review
• Hyatt Regency Maui Review
• Hana-Maui Resort Review