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Reinventing the Classic Hawai‘i Family Vacation for a New Generation

By Michelle Baran

Mar 30, 2022

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A lei making lesson at Four Seasons Resort Maui at Wailea

Photo by Michelle Baran

A lei making lesson at Four Seasons Resort Maui at Wailea

As Hawai‘i drops all of its pandemic-era travel restrictions, this is a chance for families to return to the islands with a stronger appreciation of nature and of Native Hawaiian culture.

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My first time traveling to Hawai‘i was as a young girl in the 1980s. Back then, my travel-loving parents compiled what would have been considered the ultimate Hawai‘i family vacation. We spent time in Honolulu on Oʻahu, where my brother took longboarding lessons on the famous Waikīkī beach. We attended a luau, where my family got a kick out of forcing me onto the stage for a group hula lesson. And we hopped over to Kaua‘i, where we stayed at the legendary Coco Palms Resort (sadly still shuttered since hurricane destruction in the 1990s), a property that was built on ancient Hawaiian royal land.

By many measures, it was an awesome getaway. Looking back, however, I realize that it was maybe missing something.

The writer's brother on Waikīkī circa 1984 (left); taking part in a hula lesson at a luau in Oʻahu (right).

In the years since, I have been back several times. During these journeys to the Hawaiian Islands, what’s been lacking was an effort to dig deeper into the destination for a fuller understanding of the history, the culture, the environmental issues, and the challenges Hawai‘i and Hawaiians face, and the ways we as visitors impact the economy, the identity and the sustainability of the islands.

Not long before traveling to Hawai‘i for my most recent trek this past February with my husband and our two kids (ages three and five), it dawned on me that this was my opportunity to create the ultimate Hawai‘i family itinerary anew, a generation after my parents first brought me there. 

As we begin reintroducing our kids to the world beyond our immediate environs, it feels like this is a chance to do things with greater purpose than we maybe would have prepandemic when we took so many of our travel opportunities, and the destinations and people they encompass, for granted. Despite how young our kids are, we wanted them to engage in the destination in more meaningful ways that go beyond the beautiful beaches and the waterslides at the hotel pool.

To be clear, we are not model parents in any way. As a family, we let a lot of things slip during the pandemic. Screen time went through the roof, we have succumbed to shamelessly bribing our kids with treats in just about any stalemate situation, and our toddler’s eating habits are atrocious. We’ve honestly stopped even really trying to turn some things around as we continue on our "survival mode" path of parenting.

But this realization about how we as a family approach the destinations we visit is about so much more than just us.

On March 26, Hawai‘i dropped all of its domestic COVID travel restrictions for the first time since the start of the pandemic, effectively opening the floodgates for travelers to return, en masse, to these beautiful islands. As families head back to paradise, are there actions they can take to improve the experience for both visitors and their island hosts and that can help better preserve the destination for generations to come?

What we found is that by making some efforts to incorporate additional educational and cultural elements into our trip with our kids, to connect them more with nature and with Native Hawaiian traditions, the entire journey was so much richer, more fulfilling, and honestly more fun and memorable, than it would have been had we just sat by the pool or laid on the beach. (Don’t worry, there was plenty of pool and beach time, too.) 

Creating a pretrip Hawai‘i reading list

Before heading out, I ordered some books for both the adults and kids so that we could better educate ourselves on Hawai‘i’s history and culture.

For the adults, we bought Shoal of Time: A History of the Hawaiian Islands by Gavan Daws. It doesn’t get more comprehensive than this if you really want to go back to the roots of how and when Hawai‘i was discovered and the interactions that ensued between the islands’ original inhabitants and foreign settlers.

We also made sure to read some important recent articles about Hawai‘i, including AFAR’s “Hawai‘i Is Not Our Playground” by Chris Colin, which was, quite frankly, the impetus for my new way of thinking about how we visit. I consider it required reading for anyone heading to the islands as well as anyone who wants a deeper understanding of the tensions between visitors and locals. I also delved into Bloomberg’s coverage of the greater role Native Hawaiians are playing in shaping the path forward for Hawai‘i’s tourism industry and the cultural renaissance that is underway in Hawai‘i.

For the kids, we got A is for Aloha: A Hawai'i Alphabet, a great A-through-Z children’s book that serves as a solid primer on Hawaiian culture and history. We also got them a trio of folktales: Māui Hooks the Islands, Pele Finds a Home and Hina, to introduce them to the islands’ rich tradition of storytelling.

Developing a fun, kid-friendly Hawai‘i trip that gives back

Before we decided exactly where we wanted to go, we first had to zero in on what exactly we wanted to do while in Hawai‘i.

The Hawaii Tourism Board has developed a “Mālama Hawai‘i” or “give back” to Hawai‘i initiative, aimed at providing travelers with ways in which they can volunteer and engage in activities that benefit the islands. This is a wonderful place to start and a great resource for families researching activities they can embrace that aid in sustainability efforts, while also strengthening visitors’ understanding and appreciation for Hawaiian culture.

Here are some of the pillars of the itinerary we developed based on the Mālama Hawai‘i premise as well as some additional recommended activities. 

Ethical animal encounters

The writer's husband and son watch a humpback whale from a kayak.

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One easy and effective way straight to young children’s hearts is through the wonder and beauty of animals—what kid doesn’t love animals?

We were lucky enough to be traveling to Hawai‘i during the winter whale migration season. Thus, we did a kayaking whale watching experience with Maui Undersea Adventures at Four Seasons Resort Maui at Wailea that blew our son’s mind when he got within feet of a humpback whale. There are also numerous ways to safely spot sea turtles throughout Hawai‘i and explore tide pools where the whole family can search for sea critters.

The Waikīkī Aquarium and Maui Ocean Center (we visited the latter) are great examples of venues where you can get the kids to engage with marine life and learn more about their ocean environments, what threats they face, and how visitors can help.  

For older children, learning how to safely and respectfully snorkel and scuba dive is another option for getting up close with nature. And there are also numerous birding trails throughout the islands that novice bird lovers can embrace.

Helping the environment

The writer and her kids plant a milo tree at Gunstock Ranch in Oʻahu.

Animals really help to get the message across to kids about how important it is that we safeguard their habitats. We used our kids’ love of animals to help us motivate them to do a bit of “work” while in Hawai‘i, whether that meant a beach cleanup project (such as a self-guided cleanup we did at Four Seasons Maui in Wailea, a program that was created in partnership with the Pacific Whale Foundation) or planting a tree as part of larger reforestation efforts across the state (we did this at Gunstock Ranch on Oʻahu’s North Shore and it could not have been a more special and rewarding experience for us as a family to do together). Little actions can have a big impact.

We devoted some time to walking along the beach in Wailea grabbing any trash or debris we could find. (Honestly it wasn’t more than 15 or 20 minutes since kids this age don’t have much patience—but we still picked up a fair amount.) I then asked my son Niko if he knew why we were doing this. “To protect the ocean and keep the animals safe,” he responded. Clearly, the point was getting across.

We wanted them to understand the critical role they can play in not just keeping the environment clean, but also in helping gorgeous destinations like Hawai‘i to be able to survive and thrive.

Authentic cultural moments

Four Seasons Resort Maui at Wailea is hoping to educate guests about the importance of hula beyond just the entertainment value.

One thing that has weighed on me during my travels is how to decipher whether the cultural experiences being showcased for visitors are actually authentic. I have always wondered: Is this just a show for the tourists? Or is this a performance or experience that is being proudly shared as a way to help preserve the culture? 

“Luau shows are specifically for the purpose of entertainment. It is for enjoyment. What cultural value do you get out of that? It’s beautiful. But there’s so many people there, the culture gets lost,” says Wendy Tuivaioge, director of Hawaiian Programs and cultural ambassador at Four Seasons Resort Maui at Wailea.

Rather than attend a luau, we looked for more intimate cultural experiences we could do with the kids where they could hear the stories behind the customs from Native Hawaiians, ranging from a lei making class to star gazing experiences. Even visiting the cultural sites at Waimea Valley on Oʻahu’s North Shore was an opportunity to see how Native Hawaiians lived, practiced medicine, and worshiped hundreds of years ago.

Exploring a traditional Hawaiian living site at Waimea Valley.

The more 1:1 encounters our family was able to have with Hawaiians, the stronger the connection and the deeper the understanding. I loved sitting back and listening to locals tell my kids about their traditions and seeing it slowly sink in for them—because we all know it’s better consumed and grasped coming from anyone other than us parents.

Hotels in Hawai‘i with enhanced cultural and sustainability programs

Once you decide what you want to do, it’s time to decide where to stay. For us, the aim was to stay at hotels or resorts that have put an emphasis on authentic cultural programming and sustainability initiatives. Hotels and properties that do this well serve as an ideal destination for families who want to travel to Hawai‘i with greater intent.

Four Seasons Resort Maui at Wailea

Enhance your stay at Four Season Resort Maui at Wailea with a plethora of educational activities.

Not only does the Four Seasons Resort Maui at Wailea represent the epitome of island luxury, but the cultural programming here also is at the forefront of the Hawaiian renaissance movement, thanks in large part to Tuivaioge, also known as “Aunty Wendy,” who is helping to develop rich cultural and educational experiences for guests of all ages.

During our stay, my son and I did a lei making class with Tuivaioge, who has been making the decorative floral wreaths for most of her life. She explained the origins of the craft and what the different types of leis mean as we wove together our own.

The resort’s complimentary Kids for All Seasons program (for kids ages 5–12) is also infused with educational elements, such as a tide pool exploration that our son participated in, during which he learned about and held a pencil urchin and the hermit crabs that call the tide pools home, and about the fragility of their habitat. The resort also just launched Ocean Aloha, a new activity hosted in partnership with the Maui Ocean Center. Marine naturalists will be coming to the property during spring break and the summer season to teach kids about the ocean ecosystems. And as mentioned above, guests can engage in a beach cleanup intiative, too.

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While we were there, we also got to experience a stargazing lesson with Hawaiian navigator Kala Babayan Tanaka, a mother and wayfarer whose stories of using the stars to help her navigate the oceans are incredible—she is wonderful with kids of all ages, including even squirmy three year olds. Tanaka is hosting a Hawaiian Star Stories series this spring and summer.

For a more in-depth look at the hula tradition, the resort recently launched a Behind the Scenes of Hula experience whereby guests get a sneak peak of the competitive world of hula dancing by observing Tuivaioge’s hula school practice as they prepare to head to the Merrie Monarch Festival, a showcase of Hawaiian culture and a premier hula competition.

“Hula is our life because it tells us where we came from,” Tuivaioge told me during our February visit. “When I do my classes, it’s not only about just doing. It’s about talking about it, explaining it. What is the meaning?”

Turtle Bay Resort on Oʻahu’s North Shore

Embrace Hawai‘i's deep ranching history at the Stables at Turtle Bay Resort.

To further expand on our journey, we headed to the recently overhauled Turtle Bay Resort on Oʻahu’s North Shore, a truly unique destination—Turtle Bay Resort is the sole resort property at the northernmost tip of Oʻahu. The drive here from Honolulu is a gorgeous one-hour trip past soaring green cliffs and along crystal-clear blue water. Once at Turtle Bay, families will feel a world away from the skyscrapers of the Hawaiian capital.

The reborn resort is effortlessly stylish and has a very distinct sense of place, marrying together the North Shore’s epic surfing cred, the natural wonders of the surrounding environment (true to its name the area is home to numerous sea turtles), and the region’s deep ranching roots.

The property offers a long list of experiences (for an added cost) that guests can sign up for to dig deeper into the local culture and nature, such as bird-watching tours, cultural bike tours, kayaking in search of sea turtles, stargazing (we opted for this, which involves looking through a massive telescope with a local astronomer—the kids loved being in a field in extreme darkness and finding out more about the night sky), and ukulele lessons.

Turtle Bay Resort also hosts a Kahuku Point restoration workday on the second Saturday of each month during which volunteers work with the North Shore Community Land Trust to remove invasive species and debris and help restore the coastal sand dune ecosystem at Kahuku Point.

Additionally, the Stables at Turtle Bay just launched a new Paniolo Pāʻina (paniolo is Hawaiian for rancher and pāʻina means party) experience that celebrates the region’s rich ranching history (which dates back to the 1800s) with authentic farm-to-table food, plus music and dancing. The Stables is also a great place for horseback riding—the trails have some of the best views I’ve ever seen on horseback with a ocean backdrop—another way to get a taste of the islands’ ranching tradition.

While at Turtle Bay, we also took our kids to nearby Gunstock Ranch for a tree planting experience. The milo tree planting effort here is part of the larger Hawaiian Legacy Reforestation Initiative. Since it was founded in 2014, more than 400,000 trees have been planted in Legacy Forests located throughout the state. (Gunstock Ranch is also a working horse ranch and another good choice for riding.)

Turtle Bay Resort also has a charitable arm, the Turtle Bay Foundation, which provides educational scholarships, job training, and grants for environmental stewardship and historic and cultural preservation to North Shore communities.

‘Alohilani Resort Waikīkī Beach

Families will love the aquarium in the lobby at ‘Alohilani Resort Waikīkī Beach.

‘Alohilani Resort Waikīkī Beach is working toward achieving carbon neutral certification (which it will have verified by global certification organization DEKRA). It plans to be mostly carbon neutral by the end of 2022. One of its carbon offset programs is the Hawaiian Legacy Reforestation Initiative. The chic property’s commitment came full circle for us because it’s funding reforestation efforts that include the tree planting initiative at Gunstock Ranch on the North Shore that we participated in. The resort is powered by 100 percent renewable electricity and has partnered with Beach Candy Waikīkī to offer guests credits (which are included in the resort fee) for beach rentals to help reduce waste. The impressive onsite aquarium in the lobby also helps to connect kids with marine life while staying at the property.

Grand Wailea

Kalei ‘Uwēko‘olani is the cultural programming manager at Grand Wailea Maui, A Waldorf Astoria Resort, where she is working to safeguard Hawaiian culture for both guests and staff alike. That includes having recently launched a new family-friendly outrigger program allowing adults and kids to sail on a traditional outrigger canoe along the coast of Wailea. Families can also take ukulele and kukui nut bracelet weaving lessons, among other cultural experiences.

Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua is an extremely family-friendly luxury resort with ample programming aimed at kids, including Jean-Michel Cousteau’s Ambassadors of the Environment program that teaches kids about the importance of protecting the environtment. Here, Clifford Nae‘ole’ serves as Hawaiian cultural advisor, ensuring that the cultural experiences and representations throughout the property are respectful.

Montage Kapalua Bay

This luxury Maui property has two cultural ambassadors, Silla Kaina and Kahokule‘a “Hoku” Haiku, telling the story of Native Hawaiians to guests. “By sharing and educating others about our culture and history, this creates a deeper respect for our ancestors and the knowledge they possessed,” Kaina tells AFAR. Together they have created a roster of daily cultural classes focused on traditional Hawaiian values, such as hula and Hawaiian language lessons. Montage Kapalua Bay also recently launched a heritage cooking program that invites guests to learn all about traditional Hawaiian dishes, including poi and lomi-lomi.

>> Next: The Best Hawaiian Islands to Visit for Different Kinds of Travelers

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