Do horses zipline? How we discovered the answer on Maui

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By Christopher Elliott

Horses aren’t the first thing that comes to mind when you think of Hawaii. Palm trees. Pineapple plantations. Luau. Hula, maybe.

But horses? No. And definitely not cowboys. But in Maui’s upcountry, far from the beach resorts and the gentle surf and the postcard-perfect waterfalls, there I was, confronted with a funny question.

“Dad, which horse goes down the zipline?”

My six-year-old son, Iden, who’s a pro at coming up with riddles like that–unanswerable ones, usually–was totally serious. He’d seen the zipline course at Piiholo Ranch, on a hillside that leads up to one of Maui’s dormant volcanoes, and then horses, and he’d connected the dots.

“Horses don’t zipline,” I said.

But then I pictured it: Cavalier, the mild-mannered horse he was learning to ride that day, somehow harnessed to a steel cable. What kind of noise would it make as it plummeted down the hill? Would a zipline even support the weight of a horse?

“Do you think I could ride Cavalier down the zipline?” asked Iden, still unconvinced.

“I don’t think so,” I laughed.

“Are you sure?”

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“Pretty sure.”

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Cavalier’s trainer, Amy, was eager to show Iden the ropes. She helped him get on the horse, taught him how to hold the reins, and how to ride him correctly. (But alas, no ziplining.) Iden smiled ear-to-ear from the moment he laid eyes on Cavalier until he got into the rental car to drive back to the Grand Wailea, on the other side of Maui.

Unfortunately, Maui’s upcountry is frequently skipped by visitors. If you do, you’ll miss the horses and the cowboys, called Paniolos, and some of the most gorgeous views of what many say is Hawaii’s most beautiful island.

If you make it up there, be sure to check out Bev Gannon’s restaurant, the Hali’imaile General Store. Her fusion cuisine is not only some of the most celebrated on the island, but the restaurant is child-friendly with kids’ fare more than the standard chicken tenders and burgers. Gannon puts just as much effort into pleasing her youngest customers.

Not everything on Maui is for kids, at least not kindergartners. We went surfing over at Goofy Foot Surf School on the west side of Maui, and Iden just didn’t see the point of getting on the board.

The challenges of hiking with a six-year-old

He did, however, love the attention from the girls at the shop and eagerly showed them how to draw giant waves. I got in the water with owner Tim Sherer but proved to be anything but the ideal student. When you’re trying to watch your child on the beach with one eye and catch a wave with another, can you say “wipeout”?

Why was Iden drawing giant waves, you ask? Because we were awakened by tsunami warning sirens on our first morning on Maui and were evacuated to the fourth-floor lobby of our resort. The giant wave ended up being only three feet tall, but it left a lasting impression on my son. In his imagination, it was considerably bigger.

There are a few things you don’t want to have to tell your kids when you’re traveling. One definitely is: Wake up, there’s a tsunami coming our way. The other: There’s been a fire on our aircraft. We’re making an emergency landing in Honolulu. (Yes, it happened. We had a tsunami warning and an emergency landing. Thankfully, we survived both.)

Hiking the waterfalls is another Maui experience best skipped if you have a six-year-old who would really rather dive into the hotel pool.

Although we had a first-rate guide from Hike Maui, and even though the three-hour hike through the hills was beautiful, Iden continuously asked, “Are we there yet?”

From lazy rivers to oceanic wonders

“Are you kidding?” I said. “Look at the gorgeous waterfall! What are those, coffee plants? Is that an avocado tree?”

He was unimpressed. Kids will be completely honest with you at this age. All he wanted was a trip down the lazy river at the Westin Maui on Ka’anapali Beach and a shave-ice. Not necessarily in that order.

The Maui Ocean Center (also conveniently located next to a business that sells shave-ice) is another place worth visiting if you’re traveling with a kindergartner. Although it isn’t as sprawling and comprehensive as some of the mainland aquariums I’ve seen, it makes up for its small size by specializing in many of Hawaii’s unique marine life, including whales and dolphin. The Ocean Center’s exhibits were truly immersive, lowering you from one ocean level to the next and showing you what lives there.

If you find yourself on the west side of Maui, be sure to check out the Sugar Cane Train, a vintage train that once hauled sugar cane crops around Maui. It’s a slow journey from historic Lahaina to the Kaanapali Beach, through residential neighborhoods, golf courses, and over an old wooden trestle. There may be no better way to see Maui’s impossibly gorgeous beaches than from the seat of an antique train.

Authentic Hawaiian culture

Like the horse ride at Piiholo Ranch, the train trip made me curious about having a more authentic Hawaii experience. While resorts like the Grand Wailea and the Westin are ideal places for families, offering almost every conceivable creature comfort and amenity, we found that another nearby property, the Kaanapali Beach Hotel, went in a different direction. The staff members here have built a dugout canoe and are constantly celebrating Hawaiian culture as they practice the art of hospitality. Let me put it this way: I’ve never seen hotel staff sing more than I did when I visited this resort. Iden might have been a little young to understand the connection between hospitality and Hawaiian culture. I’m sure he will in a few years.

Ask me about Maui, and I’ll tell you about its stunning beauty–how the whole island looks as if someone turned the color saturation up by just too much. The blue sky is a little bluer; the green hills an emerald green and the ocean is a brilliant turquoise. And I’ll tell you about how friendly the people were. (Here’s how to survive a long flight in economy class and avoid jet lag.)

Ask Iden about his island adventure, and he’ll talk at length about the various flavors of shave-ice he tried and resorts with extravagant swimming pools.

And he’ll tell you that one day when he comes back to Maui, he’ll take Cavalier ziplining.

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Christopher Elliott

Christopher Elliott is the founder of Elliott Advocacy, a 501(c)(3) nonprofit organization that empowers consumers to solve their problems and helps those who can't. He's the author of numerous books on consumer advocacy and writes three nationally syndicated columns. He also publishes the Elliott Report, a news site for consumers, and Elliott Confidential, a critically acclaimed newsletter about customer service. If you have a consumer problem you can't solve, contact him directly through his advocacy website. You can also follow him on X, Facebook, and LinkedIn, or sign up for his daily newsletter.

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