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10 Family Adventure Highlights from Maui


Maui Sunset

If nature adventuring as a family is your jam and Maui is your family travel destination, then skip the hours of research I already did and copy our vacation highlights (sharing is caring, right?)!

Let’s start with some logistics. We spent 11 days on the Hawaiian island of Maui, which felt like just the right amount of time to experience all we dreamed of at the slow pace that leaves the space to absorb and enjoy it. As homeschoolers especially, we need the freedom to explore and question and process. This is a lifestyle for us, so we are intentional about holding a healthy, slow pace. We got back from our trip feeling rested and renewed, not exhausted and worn down. Whether you plan to spend 3 days or 30 on this trip, don’t overpack (in every literal and metaphorical sense of the word).

The best time to travel to Maui is in September (in my thoroughly researched opinion). The tourists are gone (thanks traditional public school!), the summer prices are down, and the weather is perfect. We always travel in these shoulder seasons, as they’re known in the travel industry, which give you the best bang for your buck.

Google flights will show you the cheapest flights given your originating destination and travel dates. For us, the airline with the best deal was Hawaiian Air and I have to say, it was the best flight I’ve ever had. The safety presentations were given via videos filmed around the island of Maui, they offered good movies and even video games, and served a tasty rum punch. And speaking of transportation, after checking rates with every rental company on the island, the best price was Alamo car rental booked through Costco.

We booked an AirBnB in the city of Kihei. There are loads of hotel resorts in the bustling tourist town of Lahaina but that’s not really our vibe. We wanted a simple condo (which would give us a kitchen and beds for all our sleepers) with a pool on the beach in a more residential town. Kihei is coastal and quiet while still offering all the stores, restaurants, and shave ice nearby that a family could want. The kids were in the pool every day and we walked across the lawn to the watch the kite surfers and sunsets on the beach every evening.

Now on to the fun stuff! Below are the 10 highlights from our trip.

Jungle Zip Line

1. Jungle Zip Line

There are several zip line companies around the island but this is the only company that has a young minimum age requirement and runs through the actual jungle. We had so much fun zipping through the tree tops over the 8 lines that run through the lush northern side of the island. This was the favorite experience of the 2 youngest Rainbolts.

Though West was racing through the jungle from perch to perch and jockeying to take off first every time, I noticed a persistent fear in his eyes and steeliness in his grip that prompted me to ask him how he was feeling as he was eating clipped into yet another line that would carry him soaring over the jungle.

“This feels intimidating.”

“Yes, intimidating, and you’re so brave to move through this experience with that feeling. How do you feel when you lad safely on the other side?”

“Exhilarated and proud.”

“Me too. Let’s always remember that we can do intimidating things.”

Yes, these experiences are fun, but they also leave deeper character marks that my children will carry with them.

Since this activity would bring us over to the north side of the island, after our zip lining we checked out Ho’okipa Beach, where you can watch surfers and look for turtles, and then enjoyed a delicious meal at Flatbread Company in the adorable and quaint town of Pa’ia.

Snorkel Sail

2. Snorkel Sail to Honolua Bay

My favorite experience of the trip was our snorkel sail to Honolua Bay. We boarded a beautiful catamaran sailboat in Lahaina and headed north around the island.

We sailed parallel to a pod of dolphins a hundred strong who couldn’t resist our wake and swarmed the boat: little babies clumsily keeping up with their mamas, graceful acrobats leaping from the water, brave wake surfers racing inches below our feet. It was an incredible encounter—so beautiful that it brought tears to my eyes—and upon reflection I couldn’t help but think back on a lifetime of encounters feeding, petting, and ogling captive dolphins. The contrast was stark and tragic . . . and such a parallel to my experience with children in schools compared to children living and learning naturally in the real world. Honoring the wildness of all living things unleashes their natural potential and beauty.

Then we anchored in the bay and snorkeled off the sailboat. We got to explore coral, identify fish, and discover eels, but the most incredible part was swimming with sea turtles! They fed us well and we began the journey home feeling full and happy. Resting in the net on the bow of the ship with my littles was the most peaceful moment of the entire trip.

Iao Valley

3. Iao Valley State Park

This destination takes you into the lush valley of west Maui. You’ll hike up the path to the see the Iao Needle, a peak created from erosion, that in traditional Hawaiian culture was the phallic stone of the ocean god (yes, you read that right). The place averages an inch of rain per day and there are some good signs along the path that tell the history of this place. After hiking to the needle, we hiked back down and scrambled around the rocks along the stream for some really fun swimming among the locals, who were all so warm and friendly.

4. Hana Lava Tubes

The Hana Lava Tubes were the first stop on our day driving the Road to Hana. Be sure to fill up your gas tank at Costco in Kahului on the way, bring water and food for the day’s journey, and leave early. We also downloaded an app that provided gps mapped directions (no cell signal for most of the day) and a corresponding audio tour, which was a nice addition to the drive (we went with GyPSy and I hear Shaka is also good).

The lava tubes themselves were really neat though pricey (and they only take cash). Be sure to take a minute to turn off your flashlights and really feel the profound darkness. It was cool to remind the kids (I recommend learning about lava tubes in advance) that this was a solid, underground river of lava flowing from the volcano out to the sea. That realization definitely adds a thrill to the already adventurous underground hike.

Waianapanapa State Park

5. Wai’anapanapa State Park

As a child growing up in Honolulu, my husband saw this black sand beach in books and longed to feel the distinct texture of the black sand under his feet, hear the unique sound of the waves tumbling this geological marvel along the shore, smell the sea cave where the flash cooled lava tube meets the ocean spray. Needless to say, this was the favorite experience for my husband. We swam in the strong waves, explored the sea caves, and hiked along the surrounding trails. Most of the beach is more like pebbles than sand, so be sure to wear water shoes for this one.

Ohe'e Gulch

6. Ohe’e Gulch

We continued on past Hana to Ohe’e Gulch, also known as the seven sacred pools, and hiked along to the trails and falls for swimming.

As the sun was setting, we began the journey back home to Kihei and decided to drive around the backside of Haleakala instead of retracing our steps along the Road to Hana. We did not regret that choice. While the drive along the Road to Hana was full of sharp switchbacks, single lane bridges, and loads of traffic, the back way around was gorgeous and empty.

Haleakala National Park

7. Haleakala National Park

Save your parking ticket from Ohe’e Gulch and it’s good for admission into Haleakala National Park within the following 3 days. We enjoyed a beautiful and leisurely drive up through the cloud ceiling toward the peak of the volcano. Once we made it to the top, we felt like we were on Mars! This experience exceeded all our expectations. The view from the edge of the crater was incredible, the sunset through the cloud floor over the ocean was remarkable (bring chairs, warm layers, and a picnic dinner), and the stars . . . I just don’t even have the words. Stay beyond sunset for the sky to really knock your socks off as this peak has been dubbed the best place on the entire planet to view the stars.

Nakalele Blowhole

8. Nakalele Blowhole

Driving past Lahaina, and past Honolua Bay, you’ll come to a parking lot from which you can hike down the rocks to the Nakalele Blow Hole. The untouched wildness and beauty of this area felt straight out of an epic movie setting. When we were ready to move on, we continued on North around the island to eat in Kahului.

And I just have to point out that this (above) is a photo of a human child thriving in his natural habitat. After hiking down a rocky hillside in the sunshine on the wild edge of an island, he grounds himself on the slippery lava rock and bravely opens himself up to the playful spray of a dangerous blowhole. This photo makes my soul flutter. It stirs in me profound gratitude for every choices that has led us to this lifestyle we have designed around our needs – an evolutionary fit for living, learning, and loving.

Kameole Beach 3

9. Kameole Beach 3

Kamaeole III was our boogie boarding spot, which made it the favorite beach according to my crew. It was always pretty crowded on this small stretch of beach and the shore break was often brutal, but that didn’t stop my family enjoying the fun to be had here. This also provided us the opportunity to drive as far south as the coastal road goes, which completed our full trek around the island.

Lahaina Luau

10. Old Lahaina Luau

A luau is a cultural must and the Old Lahaina Luau offers an extravagant version of one that we all really enjoyed with hula dancing, open bar, leis, all-you-can-eat buffet, and live music. Is it fake and touristy? Sure. But I really longed to incorporate the cultural piece and this was the only means I found to formally accomplish that. Plus, I mean, a girl can enjoy gettin’ fancy for one night, right?

This trip was so wonderful. And not just because Hawaii is paradise (having been born and raised in San Diego myself, I’m not really impressed by sunshine and palm trees). But because of the incredible experiences we shared together as a family. And I’m sure you will too.

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I work from an island in the Pacific Northwest, where I live wild and free in connection with my hilarious husband and three growing sailors in our fixer upper on the beach. I authentically live this healing work out loud raising my own neurodivergent family (inner child included) and draw on my decades of education and experience (I've done all the nerdy work so you don't have to) to guide a revolution of overwhelmed parents just like you to feeling at peace within yourself, consciously connected with your children, embraced by a supportive community, and enjoying a values-aligned life you love.

Gentle parenting, natural homeschooling, & simple living mentor

I'm Rachel Rainbolt

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