Christie Porter and Jeremy Pugh

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. 

For the best view of the island, consider taking a road trip through Maui. We’ve compiled the best pitstops and excursions so you can sit back and enjoy the ride.

Roadtrip One: Upcountry on Kula Highway

Start—Paia
End—Ulupalakua

On the slopes of Haleakala, tour farms and ranches and peruse local art galleries and markets steeped in the history of Maui’s Paniolo (cowboy) culture. There will be plenty of fresh snacks along the way, finished with a flight of local wine. 

1. Paia Town

This historic town on Maui’s North Shore was once a booming plantation town during the height of Maui’s sugar cane industry. Today, Paia is a town of colorful storefronts, local art galleries and one-of-a-kind boutiques and restaurants. On your way out of town, tour the Haliimaile Pineapple Farm and distillery and grab some Maui Gold pineapple to take home. 

2. Makawao Town

Makawao is a thriving arts community that has kept its plantation roots intact. The combination of its paniolo heritage and its lively art scene makes for great pop-up markets to eclectic art galleries. The Hui Noeau Visual Arts Center hosts free exhibits and T. Komoda Store & Bakery has been serving cream puffs since 1916. 

3. Pukalani

Boasting spectacular views of two Maui coastlines, Pukalani has a laid-back, country feel. It is home to the Upcountry Farmers Market, which has a wide selection of local growers and producers. Visit one of Maui’s last true mom-and-pop establishments, the Pukalani Superette. 

4. Kula

Kula is in the heart of Maui’s Upcountry and in the middle of a culinary resurgence. Harvest your own veggies and have them made into a gourmet meal at Oo Farm, visit the one-man working protea and coffee farm, Shim Coffee Farm, play with the animals at Surfing Goat Dairy or tour the Kula Botanical Gardens.

5. Ulupalakua 

Blink and you’ll miss the small town of Keokea, but the old-time gas station, art gallery and country general store are worth a visit. Then continue down the road to the Ulupalakua Ranch Store & Grill (famous for their elk) and, finally, reward yourself with a flight of your new favorite wine at Maui Wine.

Roadtrip Two: Hana Highway

Start—Haiku
End—Kipahulu

Hike to waterfalls and through rain forests, sun on stunning black or red sand beaches and eat the best banana bread you’ve ever had. Do it on your own or hire a guide (or the middle option of downloading a guided tour app like GPSY). Spread it over two days or start early and try to do it all in one. Even though it’s only 50 miles or so, the one-lane bridges, tight turns and incredible views will slow you down. Be sure to stay on the main drag out of respect for the locals who don’t want to be a tourist attraction.

1. Haiku

You’re going to want coffee for this road trip, so start off with a cup of joe in Haiku at Jaws Country Store. From there, it’s not far to the Garden of Eden Arboretum or the Leilani Farm Sanctuary in Haiku to see the local flora and fauna up close.

2. Keanae Peninsula

While technically a slight detour from the famous Road to Hana, the ocean views from the Keanae Lookout will change your life, as will a loaf (or two) of fresh banana bread from Aunty Sandy’s Famous Banana Bread. In 1946, the entire community was almost wiped out by a hurricane and the only building left standing was the local church, which you can still see today.

3. Nahiku Marketplace

Another great place to stretch your legs (and take a potty break) is the Nahiku Marketplace—where you’ll find some outdoor dining. There’s coffee, smoothies and more tasty banana bread at the Nahiku Cafe and an open-air BBQ. Find locally made gifts at the Nahiku Gallery. Between the marketplace and Hana, you’ll find Coconut Glen’s, which people swear by, if you’re game for vegan coconut ice cream. 

4. Hana

Get a parking reservation in advance to swim and sunbathe on the beautiful black sand beach at Waianapanapa State Park. Or take a (slightly scary) little hike to find the more secluded red sand beach, Kaihalulu Beach. Explore the Hana Lava Tube or Wailua Falls and swimming hole. For souvenirs to commemorate the drive, try the Hasegawa General Store and Hana Ranch Store.

5. Kipahulu District (Haleakala National Park)

A final stretch of stunning rainforest and waterfalls will take you to the Kipahulu District entrance of Haleakala National Park and access the Pipiwai and Kuloa Point trails. The Kuloa Point Trail will take you on a short walk to the Hale Halawai, a reconstruction of a traditional Hawaiian meetinghouse, archeological sites and the Ohe’o Gulch. The Pools of ‘Ohe’o are a stunning series of tiered pools fed by a waterfall, sometimes called the “Seven Sacred Pools.”  

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Go Big on The Big Island

The Big Island truly lives up to its name (which is actually Hawai’i, while the entire state’s name is Hawaii, which feels like a practical joke to confuse Haoles). Anyway, it’s big. So it’s best to divide your time between its two distinct sides: Hilo Side (wet) and Kona Side (dry). 

Hilo Side

Hilo Bay, at the center of Hilo Town, is a good place to start your exploration of the main “city” on the wet side. From the Bay, it’s an easy walk to Liliuokalani Gardens and a stroll through Hilo’s Farmer Market to pick up picnic supplies. Richardson’s Beach Park offers a gentle put-in for snorkeling. From Hilo, drive to Volcanoes National Park for a chance to see the constant volcanic activity bubbling below the surface. 

Kona Side

Visit Pu’uhonua o Honaunau National Historical Park (The Place of Refuge) a fascinating dose of early Hawaiian history established on the site of a sanctuary and sacred place of peace. 

Nearby is the snorkeling hot spot Kealakekua Bay and the Captain Cook Monument. You can access the monument by kayak or book a charter with Captain Zodiac Raft Tours and enjoy snorkeling in the bay near the monument. The eastern side of the island is home to its best sandy beaches. The most popular sandy beach on the east side is Hapuna Beach, be sure to plan for some sand and surf time here. One of the most unique ocean experiences in Hawaii is the opportunity to dive or snorkel with the pod of Manta Rays that live off the coast. Book a charter at the Kona Marina (book early, they are insanely popular). Kona Village is the main city on the Kona side. Explore shops, restaurants and bars on its main street. The Royal Hawaiian Hotel has a beautiful ocean-view bar and an excellent happy hour. 

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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. 

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. 

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.

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

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

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 airbnb.com and vrbo.com, 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. 

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Find more adventures in our 2022 Travel Series here!