Our 6-Day Itinerary to Maui with 3 Kids and 4 Grandparents
Table of Contents
- Introduction
- Quick Itinerary Overview
- Accommodations
- Places We Ate
- Travel-friendly Activities for Kids
- Other Special Items Worth Packing
- Day 1: Arrival Day
- Day 2: Relaxation and Local Exploration
- Day 3: Haleakala Sunrise
- Day 4: Whale Watching and Luau
- Day 5: Road to Hana Adventure
- Day 6: Beach Day and Family Photoshoot
- Day 7: Departure Day
- Conclusion
Introduction
My husband Avik and I first visited Maui 10 years ago when he was attending a medical conference there and I was his plus one. At the time, we split our stay between a couple of days in Honolulu and a couple of days in Maui. While we did experience some major attractions like the Haleakala sunrise and part of the Road to Hana, we didn't cover a whole lot of ground.
This time, we spent six whole days in Maui. We repeated some activities from our previous trip, but also did a ton of other things. Even though it had been ten years, it was refreshing to see familiar locations through the eyes of not just our kids but our parents, too—this was everyone else's first time visiting.
During our first trip, Avik and I barely made it halfway through the Road to Hana. We turned around probably a third of the way because it started raining heavily, and the narrow roads felt unsafe. We never actually completed the journey to Hana. This time, however, we went all the way to Black Sand Beach, which is essentially one stop before the town of Hana itself.
We visited Maui during the second week of April. The weather was typically in the eighties during the day with lows around the sixties. It only got chilly early in the morning or at night. Overall, the weather was beautiful throughout our trip.
Quick Itinerary Overview
- Day 1 (Thursday): Landed in Maui (1 PM), check-in to condo (4 PM), grocery shopping, dinner at condo
- Day 2 (Friday): Relaxation day at the hotel pool and beach, Kapalua Coastal Trail, beach Holi celebration
- Day 3 (Saturday): Haleakala sunrise tour (3 AM departure), Iao Valley State Monument, Ululani's shaved ice, Mexican dinner
- Day 4 (Sunday): Whale watching, food truck dinner, South Maui Gardens luau
- Day 5 (Monday): Road to Hana, sea turtle beach Hoʻokipa Beach, Garden of Eden, famous banana bread, Black Sand Beach
- Day 6 (Tuesday): Relaxation day, family photoshoot with Flytographer, sunset at Maluaka Beach
- Day 7 (Wednesday): Final morning in Maui, lunch at The Gazebo, Costco for souvenirs, late afternoon flight home
Accommodations
The only reason we didn't book a hotel was because we wanted to stay together as a family rather than having everyone in separate hotel rooms. Even with connecting rooms, it wouldn't have provided the same experience. I also knew my kids are picky eaters, so I wanted the flexibility to make our food, at least breakfast in the morning. Since there aren't any all-inclusive resorts in Maui, a condo felt like the best option.
We stayed in a 3-bedroom, 3-bathroom condo at the Luana Garden Villas, which we booked directly through Maui Resort Rentals (as opposed to Airbnb, which came out to be slightly cheaper). It came with a living room featuring a pullout bed, and they provided a playpen for my son, who still sleeps in a crib at home. The unit included a full kitchen with all appliances and a patio. We specifically chose a ground-level unit because of my mom's arthritis—I wanted to avoid stairs. This choice turned out to be extremely convenient as the pool was nearly right outside our door.
I loved the spaciousness of the condo. For the first time, it felt like our family wasn't climbing on top of each other. We had more than enough space for all our bags, shoes, and everything else. The place had a dining room that seated at least 6 people, plus an island with 4 seats. There were TVs in all the rooms, and everything was really clean when we arrived.
While you are responsible for your daily cleaning (there's no room service), anytime we had an issue like something not working, we would email the management company and receive an almost immediate response. It was nicer than a typical Airbnb because the condo was professionally managed, and I would highly recommend it to anyone.
**Location Tip**: We stayed in West Maui, but if I were to go back, I would stay in Wailea (where the Four Seasons and Fairmont hotels are located). That's also where we had our photoshoot. In retrospect, I didn't know they had similar condo units there, too, which were very comparable price-wise. The reason I say this is because many of our activities required us to drive close to Wailea anyway—it would have cut down our commute time if we had stayed in that part of the island instead of in West Maui.
Places We Ate
Travel-Friendly Activities for Kids
I bought a bunch of new stuff, but my kids only played with a handful of them, listed below:
Other Special Items Worth Packing
- Travel Tray Cover Table - this is especially helpful if you're bringing crayons/markers/ etc that can easily roll off the tray on the plane
- Airplane Foot Rest - my knees get really stiff on flights, so this foot rest was a lifesaver for me, and it will be coming with me on all flights going forward.
- Hand Warmers - buy now, thank me later.
Day 1: Arrival Day
We left on Thursday morning from Newark (EWR) Airport and took a flight to Chicago. From there, we had a really short layover—made it seamlessly—and flew straight to Maui.
This was the first time we were flying with our kids (ages 3, 5, and 8) on such a long-haul flight. We normally take flights about 4 hours max, from New Jersey to Cancun, Mexico. So this was our first experience on a flight that was essentially 10 hours, with travel time extending over 12 hours.
Taking such an early morning flight is nerve-wracking even when I'm traveling alone. So with 3 young kids? My husband and I were so nervous, but the kids surprised us in the best way possible. The entire trip surprised me. I pushed them out of their comfort zone, and every time I thought they would give me a hard time or push back or drag their feet, they didn't. They just kept rolling with the punches.
This opened my eyes to the fact that it's important to test your limits with kids, in a good way—to see what their comfort zone is. Sometimes we're the ones who limit them, rather than them limiting us as parents.
We left on Thursday at 6 AM and landed in Maui around 1 PM on Thursday. We took a short tram ride to the car rental facility. We used Hertz and rented two vehicles—one SUV and one sedan—along with car seats from the rental company. Since we were traveling with my 3 kids, my husband, and both sets of grandparents (9 people total), the SUV could fit 8 people, so we were just over by 1, but having 2 cars worked out well.
From there, it was about an hour's drive to our accommodation. We arrived at our condo around 4 PM, got ourselves situated inside, and then my husband and I drove to a nearby Safeway (about 10 minutes away) to pick up some essentials—milk, eggs, bread, butter, fruits, etc. We picked up Chinese food on the way back and had dinner at the condo. Everyone was so tired that we all went to bed early, which led to us waking up around 4-5 AM the next morning.
Day 2: Relaxation and Local Exploration
For our second day, I wanted everyone to relax after the previous day's travel. We spent the morning at our hotel's pool and on the beach. While at the beach, my younger daughter and I played Holi with colored powder that I had packed. It was so much fun, just the two of us playing, and it was beautiful seeing all the colored powder mixing with the sand. Since we were at the beach, we could easily wash off and shower afterward.
Later, we grabbed lunch and drove 10 minutes to the Kapalua Coastal Trail. The trail is beautiful and I highly recommend it for a photo shoot. It's an easy trail, which was important since we had both young children and grandparents in their 70s, including my mom, who has bad arthritis in her knees. It was just a clear-cut path that led to a beautiful manicured lawn with amazing views. Being close to our hotel was a nice plus.
Day 3: Haleakala Sunrise
In retrospect, I wish we had done Haleakala on Day 2 since we were still jet-lagged and all woke up around 4 AM naturally. For the Haleakala sunrise tour, we needed to leave our hotel by 3 AM. The summit is about a 2-hour drive from where we were staying, and since the sun rises at 6:09 AM, I wanted to give us some buffer time to arrive and layer up (it's very cold at the summit).
**Important note**: You must make reservations for the Haleakala sunrise tour, and spots get booked quickly. Put a reminder on your calendar to make reservations at least two months in advance through the official government website. I did our booking on February 15th for April 12th, FYI.
I packed snacks for everyone to eat in the car since it was too early for even McDonald's to be open for breakfast. The drive to the park entrance was uneventful, but once you reach the base of Haleakala, it's another 30-minute drive up to the summit.
Driving up the mountain at 4 AM means navigating in pitch darkness. I was fortunate that it was a full moon that night, providing some additional light, but it was extremely cloudy and foggy with low visibility. I drove slowly and carefully. Having my husband driving either ahead of or behind me in the second car provided nice moral support, ha.
For our group of nine, we split up with me driving the SUV with all three kids in the back and my dad in the passenger seat, while my husband drove the sedan with his parents and my mom. The drive up to the summit was challenging due to the foggy conditions and low visibility, but taking it slowly made it manageable.
Once we finally arrived at the summit, my kids were not happy about having to get out of the car into the cold, foggy, and dark weather. I made them put on their winter coats on top of the two layers they were already wearing, plus gloves and hat.
**Pro tip**: Bring hand warmer packs! They were much appreciated by everyone—we put one pack in each hand inside our gloves, which helped both the grandparents and kids stay comfortable. We all wore two layers of pants and about two layers of tops, including a sweater or sweatshirt and a winter coat, plus hats and gloves.
Unfortunately, it was a cloudy day, so we didn't get to see the sunrise in all its glory. We didn't have any alternative dates available since I had planned our itinerary carefully with reservations for other activities throughout our trip.
While at Haleakala, my 3-year-old was struggling with the cold and started whining. Though the sunrise was only about 10 minutes away, I felt like everyone was staring at us (he was probably the youngest person there), and I didn't want to make him endure something he couldn't yet appreciate. My husband took all three kids back to the car, where they could stay warm and rest while the grandparents and I stayed to watch what little we could see of the sunrise and enjoy a few more minutes on the summit.
This was one of those moments where, if I weren't traveling with a big group, I would have easily stayed back longer and soaked in every moment. Once the crowds leave post-sunrise, the entire summit is deserted, and it feels so serene that it makes you want to sit and meditate. (I know, I'm really showing my age here).
Hanuman in Maui
What made this experience special despite the weather conditions was that our visit fell on Hanuman Jayanti (Hanuman's birthday). I brought our Baby Hanuman plush toy to celebrate. Call me cheesy, but I thought it was meaningful being high up on the mountain—you feel closer to God in a way. My dad is a devoted follower of Hanuman, so sharing that moment with him is something I'll always cherish.
Side note: given the auspicious occasion, I was curious to see if there were any Hindu temples in Maui, since I know there is a popular one on a different island called Kauai's Hindu Monastery. In fact, our toys are carried there in their gift shop :) As it turns out, there is a small Hanuman temple in Maui, but we couldn't manage to fit it into our itinerary.
Iao Valley and Shaved Ice
After Haleakala, we headed back to our hotel to rest, eat, and freshen up. Once everyone was ready, we visited the Iao Valley State Monument. This place was breathtakingly beautiful—I can't recommend it enough! You need to make reservations ahead of time, especially since the WiFi there is weak. Walking there feels like you're entering the mountains you see throughout Maui from the moment you land. It was the closest we could realistically get to that landscape, given the grandparents' abilities.
The experience felt a bit like being transported into Jurassic Park. The trails are beautiful and easy enough for people of all ages. It is a little chilly there, so I recommend bringing a light jacket.
From Iao Valley, we went to Ululani's, one of the most popular chains for shaved ice in Maui (or possibly all of Hawaii?). There was a line, as expected, but it was worth the wait. We got a couple of different flavors that the kids loved, and it was refreshing on a warm day.
For dinner, we went to a Mexican restaurant, Roasted Chiles, which had really good food and great service. It's hard to find good Mexican food in Hawaii, in my experience, but this place was excellent.
Day 4: Whale Watching and Luau Experience
Whale Watching with Trilogy
On Sunday, we went whale watching with Trilogy. I chose this company because they're highly rated and only a quick 5-minute drive from our hotel. Even though they were priced a little higher than other companies I researched, the convenience won out in the end.
The tour was a 2-hour boat ride from 10:30 AM to 12:30 PM. We took a morning tour only because the sunset one was already sold out. One thing I wish they had mentioned (or perhaps I missed it in the fine print) is that you should wear waterproof shoes. You have to take your shoes off to walk through the water to get on the boat from the shore. If you're wearing shorts or a skirt, you don't have to worry about rolling up your pants, which makes for a drier, more convenient boarding experience.
Trilogy provided a wrap, fruits, and drinks on the boat, which was nice. We unfortunately only saw one whale, and it remained mostly underwater. We did see dolphins swimming close to our boat, which was fun for everyone. The coolest part, though, was when the whale was directly underneath our boat. We heard it making sounds, and I don't think I've ever heard a whale that close up before. That was an unexpected experience.
The weather was perfect for boating, and there was a photographer on board taking pictures that you could purchase afterward, which we did because, why not?
Food Trucks and Luau
After the boat ride, we went back to our condo to quickly change since we had another long drive ahead. For dinner, we went to a place with several food trucks. We were originally planning to try the Nirvana Indian food truck, but unfortunately, they were closed at the time. We ended up getting Thai food instead, which was surprisingly good despite my low expectations from a food truck.
From there, we had reservations for a luau at the South Maui Gardens from 5 to 7 PM. In retrospect, I wish I had known that I could have parked once for both the food trucks and the luau. On the GPS, it showed as a 2-minute drive between locations, but they're actually connected—the food trucks are on one side, and there's a little open gate separating the two areas, so you can just walk through.
I chose this particular luau because it was one of the few in Maui where you don't have to purchase food as part of your ticket. Having been to a luau during my previous trip to Maui, I knew the food wasn't exactly vegetarian-friendly (or to my taste, in general). It naturally caters to Hawaiian culture with lots of pork and meat-heavy items. Since my parents, my kids, and I are all vegetarians, it didn't make sense to pay for food we wouldn't eat. Had we known you could purchase food from the trucks and bring it to the luau, we would have just done that rather than rushing to finish eating before the show.
Another detail I missed in the reservation information was that this luau takes place on a lawn where seating is essentially BYOC "bring your own chair." They have a limited number of picnic tables, but it's first-come, first-served, and we weren't among the first to arrive. Many people had brought their own beach chairs and picnic blankets, so I wish I had known that in advance.
Despite these small hiccups, the luau was great—everything we were expecting with the traditional dances, music, and the exciting fire dance performances, which my 3-year-old described as, "So awesome!"
Day 5: Road to Hana Adventure
Another early morning awaited us on Monday. In retrospect, I wish I had scheduled all of the early morning activities earlier in our trip when we were still jet-lagged and naturally waking up early. I should have done Haleakala on Friday (our first full day) and the Road to Hana on Saturday. But we chose to do this trip on a weekday because locals recommended avoiding weekends.
Based on all the research I had done, it's highly recommended to leave for the Road to Hana by 6 AM. You want to reach the town of Paia by around 8 AM. If you start your day too late, you risk having to drive back on those narrow, curvy roads after sunset, which is not advisable. The goal is to start heading back from the end of Road to Hana by 3 PM at the latest, ensuring you have broad daylight for the return journey.
We left our hotel around 6:30 AM but had to stop at McDonald's to pick up breakfast. (I wish I had bought extra breakfast that the kids could have enjoyed later in the day, because there are limited food options once you're on the Road to Hana). By the time we reached Paia, it was closer to 8 AM, but we were still making good time. We had packed snacks, though probably not enough—or at least, of enough variety, according to my kids, who refused to eat all of them.
Pro Tip: The Shaka Guide App
One essential recommendation: download the Shaka Guide app ($23). It's worth every penny! Since my husband and I were driving in separate cars, we both downloaded it individually. Make sure to download the tour the day before your trip begins.
What's ingenious about this app is that it connects to your GPS and serves as a virtual tour guide in your car. It knows exactly where you are, makes timely recommendations about stops, and even acknowledges when you skip a suggested stop and continue straight. You don't need the GPS for navigation since the Road to Hana is literally single-lane road. But hearing the tour guide perfectly synced with your location was impressive.
Our Selected Stops
I had low expectations about how many pit stops we could realistically make. We're not swimmers, so I skipped past all the waterfall swimming spots. I had only picked three main stops (not including places to eat):
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Hoʻokipa Beach, famous for its sea turtles. There are bathrooms, and if you're lucky, fresh coconuts here as well. No reservations needed for this beach.
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Garden of Eden - We spent a good hour here. Worth noting: it has a $20 per person entry fee, but it has clean bathrooms, which made it money well spent since everyone in our group needed to use them. The views are incredible. This was a special stop for us since my husband and I had visited during our first trip to Maui ten years ago.
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Banana Bread Stand - The famous banana bread did live up to the hype. It was delicious (or maybe we were just really hungry!).
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Black Sand Beach - I had made reservations about two weeks before our trip for 3-6 PM, but we arrived around 1:30 PM. I was nervous they might turn us away for being early, but they didn't. I'm so glad, because by the time we left, it was around 3:30 PM, which is when we needed to head back to catch the remaining sunlight.
Originally, we had planned to drive to the town of Hana for lunch, but we wouldn't have made it back before sunset. So we decided to end our Road to Hana adventure at Black Sand Beach. On the way back, we had lunch at Flatbread Company in Paia, which I would recommend.
The Drive
About the drive itself—it was scary as hell for me (my husband thought the middle-of-the-night drive up to Haleakala was far more dangerous)! I'm a very cautious driver, and piloting an SUV with my kids in the car had me on high alert. The one-lane bridges were especially nerve-wracking. But I'm so proud of myself for completing the drive both ways. I feel like I've earned the T-shirt (or bumper sticker) that says, "I drove the Road to Hana!"
Day 6: Beach Day and Family Photoshoot
I decided to take it easy for our last full day in Maui. After all the planned excursions on previous days—the sunrise tour at Haleakala, whale watching, and the Road to Hana—I intentionally scheduled nothing except for one special activity: a family photoshoot on the beach.
I booked our photoshoot through Flytographer, and I'm so glad I did. While we took many photos on our phones throughout the trip, it's just not the same (IYKYK!). Having professional photos taken has become something of a tradition for us—I try to have one family photoshoot each year, especially when we're traveling to a beautiful location.
This was the first time we had the opportunity to include both sets of grandparents in our family photos, which made it extra special. Booking through Flytographer was a seamless experience. I provided a shot list to ensure we captured all the different pairings I wanted—me with my parents, my husband with his parents, the grandparents with the kids, and so forth.
We had originally planned to do the photoshoot during golden hour, but I was concerned that my 3-year-old would be too tired since he had been crashing around 6 PM on previous days due to jet lag. I moved the shoot up to 4:45 PM instead of 5:45 PM (with sunset at 6:45 PM). As it turned out, he was perfectly fine, active, and happy throughout the session.
**Parent hack**: Controversial opinion but if you bribe your kids with a toy or something they've been asking for on the day of the photoshoot, and use that as motivation for them to smile/cooperate, it works wonders! I told my kids, "Now that I bought you this [toy/thing], you promise to smile for the photos and give mommy nice smiles, right?" They kept their end of the promise, and I got amazing smiles from all three kids that evening.
After the photoshoot, we hung out at the Maluaka Beach and watched the sunset together. It was the perfect ending to our Maui adventure.
Day 7: Departure Day
Our flight back home wasn't until 5 PM, so we had a good amount of time to spend on our final day, even though we had to check out of our condo by noon.
Last-Day Activities
We had lunch at The Gazebo restaurant, which offers great brunch food right on the beach. It's a small place that doesn't take reservations, but the food is worth the wait. (Worth noting: their "waiting area" is the Napili Bay, so you won't mind at all).
Souvenir Shopping Tip
One final piece of advice: skip the over-priced boutique gift shops for souvenirs and head to Costco instead. It's just 5 minutes from the airport, making it a perfect pit stop on the way to your flight. They have great prices on macadamia nuts (a Hawaiian specialty) and a wide selection of other local products. It's also convenient if you need to fill up your gas before returning your rental at the airport.
Conclusion
This 6-day trip to Maui with our kids and both sets of grandparents was truly special. Traveling with three generations presented some challenges, but the experiences we shared made it all worthwhile.
From watching my kids push beyond their comfort zones on the long flight and early morning adventures, to sharing meaningful moments with my father at Haleakala on Hanuman Jayanti, to finally completing the Road to Hana that my husband and I had attempted 10 years ago—this trip created memories we'll cherish forever.
If you're planning a similar multi-generational trip to Maui, I hope our itinerary gives you some ideas. The island offers something for everyone, from beautiful beaches and easy trails for those with mobility concerns to adventurous drives and cultural experiences. With some careful planning and flexibility, you can create an unforgettable family vacation that accommodates all ages and interests.
Mahalo for reading about our Maui adventure!