I wrestle with my iPhone, trying to connect it to CarPlay as we race out of the Enterprise parking garage. Speed bumps ignored, the Jeep lurches and bounces like a bronco at a Texas rodeo. Was a 4×4 really necessary? The answer will be clear soon enough, but suffice it to say—hell, yeah!
Finally, I pair successfully and set up the Shaka Guide—an app designed to expertly navigate the Road to Hana—a drive on eastern Maui known for its crazy switchbacks, towering waterfalls, and dramatic landscapes.
‘It’s about the journey, not the destination,’ I tell my husband and daughter for the umpteenth time. They scowl. This is new territory for Daniel, who thinks the destination is the destination. I close my eyes and practice square breathing.
Shep Who?
When we exited Kahului Airport after twelve hours on two planes, an overnight in Waikiki, and an ungodly early morning hop to Maui, we were understandably tired (aka grumpy, under-caffeinated, and hangry). But we were on Maui. Who can complain?
I thought of my dad. As he’s mentioned more than once, one of his fraternity brothers lives on Maui. “Would you be able to meet up with Shep? You know, my fraternity brother, Shep? You’d love Shep. He’s a great guy.”
My dad has a weekly Zoom with his college buddies. And although I don’t think anyone aside from my dad gets a chance to speak, Shep is a name I hear often. My dad has great friends, all of whom are impressive and unique. My dad is a great friend. He’s also impressive and unique. Unfortunately, we don’t have time to see Shep on this trip, I tell my dad. We are driving the Road to Hana. Plus, I’m sure Shep has things to do.
So when we stumble wearily from the plane, our carry-ons and neck pillows trailing behind us, I jump when Ella shouts, “Oh my god, Mom, look!” I follow her gaze. The wall ahead has a banner that reads ‘Maui Nui Hall of Fame’ above a grid of portraits. Sandwiched between Woody Harrelson and Paul Simon is Shep. Shep Gordon. Hollywood talent manager, film agent, and producer.
Oh, and loyal fraternity brother to one Barry Lyman.
But First, (Kona) Coffee
Our hotel in Hana can take up to eight hours to reach, depending on how many fun stops one makes along the way. That’s the point of the Shaka App, I tell Daniel, ‘fun stops.’ Places to watch waterfalls, swim, hike, walk a black sand beach, climb through lava caves, and explore. It’s the journey, the journey, the journey…
This is how I knew we wouldn’t be able to meet Shep. I’d be happy if Daniel stopped for breakfast.
A perky male voice pipes up in surround sound, “Aloha! Welcome to the Shaka Guide’s Road to Hana driving tour!” Whoa, it’s too early in the morning for that kind of tone. I lower the volume. “It’s going to be a great day on our drive and tour together!” the voice continues. Ella and Daniel look nervous. I’m as thrilled as Victoria Ratliff clutching her first G+T of the day. This is going to be fantastic.
“Our trusty, albeit overeager, guide needs a name,” I say. “We’ll be listening to him for hours. Any ideas?”
“Shep!” Ella and Daniel shout in unison.
So begins our adventure along the Road to Hana.
Maui’s Most Famous Road
In the 1500s, Maui’s King Piʻilani initiated the construction of what was essentially a long, dirt footpath across Eastern Maui. The path was about 5 feet wide and stretched over 138 miles, enabling travel and trade across the island. By the 1870s, the road was improved, yet still unpaved.
It would remain that way until 1926, the official opening of ‘The Road to Hana,’ when groundwork and bridge construction were implemented for a more passable route. (I guess crossing rivers and streams by rope swing got old quickly.) Fast forward to the 1960s—a fully paved, albeit harrowing, road was complete.
By the numbers, the Road to Hana is impressive. This 64.4-mile scenic tropical drive that connects Kahului to Hana town has 620 curves (some with switchbacks that double back on themselves), 59 bridges (46 of which are single lane), over 18 waterfalls, countless beaches (some with black sand), bamboo forests, marbled eucalyptus trees, and ocean views.
Divorce Highway
Hana Highway’s switchbacks, sweetly rebranded as curves, had been on my mind since I booked the trip. Daniel and I have braved many death-defying, hair-raising, and winding roads: Corsica, Mexico, and Mallorca are a few standouts. We survived them, but not without a few heated discussions. I think he drives too fast; he thinks I worry too much about his driving too fast. We’re both right. But being right hardly matters when I’m convinced we’re about to launch off a cliff every 45 seconds.
Having Shep alert us of upcoming sharp turns and single-lane bridges eases my mind. He even describes how to share the road with the locals, who careen around curves like Formula One hopefuls.
I’ll let Shep tell Daniel to slow down, tell us where the nearest bathrooms are, and where we should stop for a snack. And he does. Hence, the Road to Hana, sometimes dubbed ‘Divorce Highway,’ is a pretty pleasant ride. Shep, if I didn’t thank you earlier, hear me now. You saved my marriage.
Navigating the Road to Hana With The Shaka Guide
Over the next three days, the Shaka Guide becomes our lifeline—highlighting 33 tour stops and 125 Tour Audio Points over 10-12 hours. I know what you’re thinking. Did Shep talk for 10-12 hours? In the downtime between talking points, the Shaka Guide played traditional Hawaiian music. The ukulele and drums set the tone—soft, rhythmic, and pure aloha vibes.
Since the Shaka app is connected to Google Maps, Shep always knew exactly where we were. Even if we didn’t. Even when it bordered on creepy. “Ignore the row of illegally parked cars ahead on the right,” Shep instructed. Then, reading my mind. “Don’t worry; better examples of marbled eucalyptus are ahead.” Sure enough, a few cars were stopped on the right, just like Shep said.
I have to give the Shaka Guide props; this kind of attention to detail is hard to pull off in real-time. To say we got more out of the drive than if we’d been reading a traditional guidebook is an understatement.
We would have missed critical turn-offs on a road where backtracking isn’t an option. We’d have missed magical views while arguing who has the right of way on 46 single-lane bridges. And we would have missed some stops altogether, clueless about what lay beyond the next bend.
It’s not called Divorce Highway for nothing.
The Road to Hana: Starting Out
The Road to Hana officially starts at mile marker 0. Shep tells us not to worry if the marker is missing, as travelers sometimes take it as a souvenir. We stop in Paʻia Town to grab a coffee and provision up. This is the first and only town we will see before we reach Hana Town in 6-7-8 hours. And although there are promises of huli-huli chicken and banana bread stands along the route, there’s no way I’m letting hanger ruin our journey.
Thanks to advanced planning, we had reserved The Hana-Maui Resort for three nights. Hana-Maui is the only traditional resort in Hana Town. With only 66 rooms and suites, it’s 620 hell-ish curves back to Paʻia Town if you don’t book one.
Check Hana-Maui Resort Availability here
Approaching Mile Marker 0
Our first stop is Hoʻokipa Beach, just off the highway past Paʻia Town. Roosters roam the gravelly parking lot, pecking with intention, while the Pacific Ocean surges below. Although called the ‘windsurfing capital of the world,’ we only see surfers sitting in the lineup and a few napping monk seals.
We return to the Jeep and drive towards the turn-off to the legendary surf break, Jaws. During the winter, we learn the waves here can reach as high as 70ft. Shep tells us to “Be aware; it’s a long and bumpy dirt road that leads to the beach.” We’re warned that the single-lane dirt track to see the break is sometimes impassable, with deep ruts and deep puddles. 4WD is a must. We skip it and vow to see it on our way back to the airport (cue foreshadowing).
Shep says we are approaching mile marker 0. If Daniel’s concerned that we’ve already stopped twice and haven’t officially started the road to Hana, it doesn’t show.
The Road to Hana: Bamboo Forests, Lava Caves, and Waterfalls
Our three days of driving are as exciting, adventurous, and scenic as I’d hoped. We see majestic waterfalls, including Twin Falls (mile marker 2) and 400-foot Waimoku Falls (mile marker 42). We trek the Pipiwai Trail, past ancient banyan trees and through tall bamboo groves, whose clacking sounds like a line of tumbling dominoes.
The sandwiches stave off hunger, as planned, but a stop at Aunty Sandy’s (mile marker 16) for a warm loaf of banana bread is the crowning culinary moment of the morning. The raging Pacific crashes against lava rocks. Palms cling to the beach and lean permanently sideways from the wind. Everything along the road feels green, mystical, and alive.
Shep tells us that if we haven’t bought tickets in advance for Waʻanapanapa State Park (mile marker 32), one of Maui’s most famous black sand beaches, we’re out of luck, as same-day passes can’t be purchased. “Ummmm, no, I hadn’t secured advance tickets,” I tell Daniel and Ella. They don’t seem to mind. Daniel probably views this as a win—an extra hour at our resort in Hana Town.
Ever the optimist, Shep reminds us there’s much more to see and do ahead. After a short ukulele melody, he has us pull off the road.
“Maybe Shep’s wrong?” Ella says as we look around. “Where’s the cave?”
But just then, we spot an opening, about three feet tall, on the edge of the highway. We peer in; it’s pitch black. ‘Trust Shep,’ I think as I scramble in. We crawl through the short, drippy, black lava cave and pop out into the forest (mile marker 23). Exhilarating and surprising, this is what the Road to Hana is about.
Hana Town: Hidden Beaches, Food Trucks, and the Hana-Maui Resort
We arrive at the Hana-Maui Resort around 4pm. It’s been a day. Miles of hairpin turns, stone bridges, gushing waterfalls, hiking, and eating. Our weathered green cottage is an oasis.—modest and clean, with 360-degree uninterrupted ocean views and an oversized veranda. We embrace stillness for the first time in days.
The only traditional restaurant in the area is at Hana-Maui, where we have two of our three dinners. But lunch steals the show in Hana Town, where groupings of food trucks keep locals and tourists well-fed. Choices abound, including homemade tacos filled with chicken, shrimp, or beef, poke bowls, huli-huli chicken, Thai food, acai bowls, and smoothies. Lunch is so good; I crave lunch for dinner. But unfortunately, the food trucks close at 630pm.
After visiting the coffee truck one morning, I sit on our deck with my book. On my left, just outside the property’s perimeter, I notice people heading down the steep hill towards the bay. ‘Where are they going?’ I wonder. Curiosity gets the best of me. Ella and Daniel are poolside, honing their Hawaiian tropic tans. I text them my general whereabouts and set off.
A ten-minute cliff-hugging hike takes me to a crescent cove with enormous red lava cinder cliffs and a red sand beach. A wall of black lava rocks absorbs the Pacific break, revealing a tranquil pool. There’s no feeling quite like discovering a hidden beach. Although not exactly hidden. As the Shaka Guide later revealed, this is Red Sand Beach (mile marker 35).
I bask in the sun and enjoy the solitude on our last full day in Hana.
Check out the Hana-Maui Resort Reviews Here
On the Road to Hana, Trust Your Guide
Our flight to Kona is at 12:30pm and the last thing I want is to get stuck on the Hana Highway. I package our early morning wake-up with the promise of one last stop at our favorite coffee truck and the chance to see anything we missed on the way up. Daniel has his heart set on Jaws.
The all-knowing Maui gods say the drive from Hana Town to Paʻia Town is roughly 2 ½ hours without stops. Daniel clocks in at 1 hour 48 minutes. He’d make a great local. So when we get to the turn-off for this mythical surf break, I’m unconcerned; we have time to spare.
Our Jeep creeps down the single-track dirt path, which gets steeper, narrower, muddier, and more deeply rutted the further we go. We cross puddles of indeterminate depth. Mud attacks the windows and obscures our view. The silence in the car is deafening. Even Shep is speechless. What have we gotten ourselves into? There’s no going back—turning around is physically impossible.
Finally, we reach Jaws, locally known as Peʻahi—one of the world’s most famous big wave surf spots. It earned its nickname from the sudden, monstrous swells that can appear seemingly out of nowhere.
We hop out of the Jeep and anxiously gaze out over the cliff. Jaws’ waves are tragically underwhelming. But none of us would have appreciated them, even if they had towered at 70ft with Kai Lenny deep in the barrel. We were too worried about the mile-long trek back to the highway. I ask Daniel what he thinks, assuming he will assuage my fears like always. “50/50,” he says with little confidence.
I start square breathing. Ella checks her phone for a signal, and Daniel puts the Jeep into gear. Off we go.
Some journeys lead to great destinations, others to great stories. On the Road to Hana, we got both.
Did You Notice?
You don’t have to be a cartographer to recognize my list of sights is geographically out of order, but they are the moments that made our journey. Use the Shaka Guide to map out your adventure. Click here to get yours!
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What an adventure. Love this one!