Road Trip: Maui

We take our time rolling up Haleakala Highway, the two-lane highway that scales Maui’s preeminent volcano of the same name. The reason for the deliberate pace is threefold—the unforgiving switchbacks enclosed scantily by the occasional guardrail, the dramatic rise in elevation (from sea level to 10,000 feet in a mere 37 miles) and the arresting views from the road. On our road trip through Maui, we coast along the highway to Haleakala Crater, there are two National Park Service visitor centers and a number of scenic lookout points, and I daresay we stopped at all of them. Facing makai (toward the ocean), the misty mountainside gives way to grassy farmland then relents to cities and sandy beaches and the endless expanse of the Pacific Ocean. Facing mauka (toward the mountain), the landscape becomes lunar-like just as it vanishes behind a halo of clouds. At the second visitor center, we shuck our breezy beachwear and change into warm pants, knit caps, jackets and gloves. 

Maui Road trip
Watching the sunset on Haleakala. Photo courtesy of Adobe Stock.

At a 10,023-foot elevation, Haleakala Crater sits above the cloud layer. The craggy peak jutting out of white cotton clouds invokes images of the mythological Mount Olympus, the home of the gods. In Hawaiian mo‘olelo (stories), Haleakala is where the folk hero Maui snared the Sun and made him promise to travel the sky slower, lengthening the day. Haleakala means “house of the sun.” People in parkas flock to the summit like pilgrims at the end of every day and this trip is no exception. We do our best to get comfortable on the nature-provided seating of rough volcanic boulders and wait. Rustling accompanies the chattering teeth and excited conversations as people produce snacks from pockets and backpacks. We brought fresh banana bread from Kula but a nearby group of geniuses had thought to drive up a few pizzas and we made a silent vow to copy them next time. 

When the sun starts to set, there are no “oohs” or “awws.” All of the noise fades at once and everyone turns their faces west. The sun touches the clouds and they erupt in gold and turquoise, and the ground around the summit turns scarlet. The colors deepen in hue and contrast as the sun sinks behind the lip of the crater, forming a golden halo as it falls beyond the clouds, then is finally swallowed by the ocean. No one stirs until the last ray of light dies. Beyond the singularity of watching the sunset from atop a volcano on a speck of land in the middle of the ocean, the reverence of the assembly makes it something more akin to a spiritual experience. 

Where to Play

To say Maui packs a lot into a little more than 727 square miles is an understatement of irresponsible proportions. Because of its unique geography and infamous trade winds, Maui has multiple distinct microclimates to play in, which help define Maui’s diverse regions. The North Shore and West and Central Maui get a lot of love from tourists, but South Maui and the Upcountry stole our hearts. 

As stunning as the Haleakala sunset is, sunrise on the volcano is the more sought-after ticket. So much so that visitors have to battle it out online for the few available permits. The area is also unparalleled for stargazing. Outside of the popular solar and stellar spectator events, Haleakala National Park has two areas for visitors to explore. The Summit District has over 30 miles of hiking trails that range in difficulty from 10-minute walks to multi-day overnight trips. One of the most popular is the 11-mile alpine desert hike, Keonehe‘ehe‘e (Sliding Sands) Trail. The trail takes hikers across the crater and through an area unofficially called “Pele’s Paint Pot” for its colorful cinder. 

Maui Road trip
Trail to Waimoku Falls. Photo courtesy of Adobe Stock.

On the eastern side of Haleakala is the coastal Kipahulu District. Unlike the blustery weather of the summit, Kipahulu District is hot, humid and wet. One of the main draws is the Pipiwai Trail, a 4-mile hike that starts at the visitor center parking lot. Early in the hike, you’ll have to contort your way through a massive Banyan tree. It’s rumored to be the second largest Banyan on Maui (the largest is in Lahaina). The trail also winds through a thick bamboo forest, culminating in a view of its crown jewel, the 400-foot Waimoku Falls.

If seeing Haleakala National Park from the ground is beneath you (literally), zip lines dot the island for your consideration. Skyline Hawaii offers guided zipline tours of Haleakala and Eco-Adventures of surrounding Upcountry Maui. 

The Upcountry was born out of the local ranches and farms and entrenched in Hawaii’s paniolo (cowboy) culture. It might as well be a completely different world from the tourist-heavy coastal towns. Explore the local farmers’ markets like Kula Country Farms or take a tour of Maui Tea Farm.

Maui Road trip
Makene Beach State Park. Photo courtesy of Hawaii Tourism Authority Maui.

If it’s the beach you’re after, head to South Maui. Kamaole Beach I (“Kam I,” 75 Alanui Ke’ali’i, Kihei), Kam II and Kam III in Kihei are lowkey and great for swimming as well as for attempting kayaking or paddleboarding. There are plenty of places to snag reasonable equipment rentals within walking distance to the beach, like Auntie Snorkel. If you’re feeling a little more adventurous, take a snorkeling tour of Molokini Crater, a crescent-shaped, partially submerged volcanic crater off the coast of South Maui. Boats head out there daily, like the Pride of Maui. If you’re feeling even more adventurous, head to South Maui’s Makena Beach State Park (4670 Makena Alanui, Kihei), commonly called “Big Beach.” The water here is crystal clear and great for a little light snorkeling. On the north end of Big Beach, there is a hidden trail to a sandy little cove called Little Beach. Little Beach is definitely not a very chill nude beach and you certainly did not hear it from us. 

Where to Eat

Banana Bread along Hana Highway. Photo courtesy of Hawaii Tourism Authority Maui.

After a day on the water, Kihei offers many dining options within walking distance from the beach. The food truck game in Kihei is particularly strong, with two locations where they tend to congregate: Kihei Food Truck Park (1 Piikea Ave., Kihei) or Alahele Place near Kihei Marketplace on South Kihei Road. For an extra kick in the morning, check out Kraken Coffee’s truck or grab a bag of Maui coffee to take home from Lava Java Coffee Roasters of Maui. For lunch or dinner in Kihei, get in line at the open-air Paia Fish Market South Side. It’s the second location of the legendary original in Paia. The Blackened Sashimi is particularly good, but you really can’t go wrong. Ululani Shave Ice is the real deal for your Hawaii shave ice fix. 

If your journey is taking you to Upcountry, Grandma’s Coffee House has been roasting and blending Maui coffee since 1918. Ulupalakua Ranch Store & Grill serves up meat from their own ranch, which you can survey while you eat your meal picnic-style near the open-air grill. For farm-to-table, there’s Hali’imaile General Store and Restaurant Marlow, a pizza place where Chef Jeff Scheer sources ingredients from local farmers and ranchers and his own garden. No trip to Upcountry is complete without a stop at Maui Cookie Lady. Founder Mitzi Toro is known nationally for the creations from her island boutique bakery.

Where to Drink

Maui Road trip
Maui wine flight. Photo by Christie Porter.

You can’t beat the views or cocktails at Hawaii Sea Spirits Organic Farm and Distillery’s on-site Ocean Organic Vodka Cafe. The distillery offers regular tours that introduce visitors to the process of making vodka from ocean water, the growing and harvesting of sugarcane varieties, as well as how to use their spirits. Our tour guide Joe could have written a book on how to mix cocktails from Hawaii Sea Spirits. The lawn outside the cafe gets crowded in the late afternoon to watch the sunset with a tasty drink in hand. Maui Wine offers tastings daily. The owner of the ranch started the vineyard and winery back in the 70s with just one kind of grape. Nowadays, they cultivate six grape varietals and make to-die-for pineapple wines made from  Maui Gold pineapple, of course. 

Back in South Maui, there’s no shortage of bars to get your drink on, but the Happy Hour menu at Maui Brewing Company is hard to beat. Between handcrafted beer, seltzers, sodas and cocktails, order a flight and a few shared plates, while dining al fresco. For the classic tiki bar experience, check out South Shore Tiki Lounge. The patio is perfect at night, and regular live music makes for impassioned sing-along opportunities.  

Where to Stay

Depending on your taste, you can spring for ocean views at a luxurious resort or rent a beachside condo in Kihei. Use your best judgment while perusing sites like and, as tourism officials warn that scams are not unheard of. For a relaxing stay in Upcountry, there’s Lumeria Maui Retreat, where you can enjoy yoga and meditation classes. It’s also worth looking into The Malama Hawaii Program. Malama translates to “care for.” In exchange for participating in volunteer opportunities, you could qualify for a discount or free night at a participating hotel. Hana-Maui Resort will give you your fourth night free if you volunteer with Pacific Whale Foundation. Condominium resort Castle Kamaole Sands, beachside in Kihei, offers a fifth night free for picking up beach litter. 

Maui Road trip
Road to Hana. Photo courtesy of Hawaii Tourism Authority Maui

Find more adventures in our 2022 Travel Series here!

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