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Road Trips

The Ultimate Maui Road Trip

You don't fly halfway across the world just to sit on a beach. For her honeymoon, JS editor Lindsey Olander (with husband in tow) embarked on the road trip of a lifetime around the island of Maui in search of the most beautiful beaches, mountain trails, fresh poke, and the true spirit of aloha.

Senior Editor, Jetsetter | @lindseytravels |

See recent posts by Lindsey Olander

All I ever wanted was for my new husband and I to relax on our honeymoon—I swear. Flying across the globe from New York to Hawaii seemed daunting enough. Driving around an entire island was not part of our plan, but somehow, somewhere along the back roads of Haleakalā, we realized we’d gone too far to turn back. I wouldn’t have had it any other way. Here’s what we got up to during our Maui road trip.

Days 1-2: 17.2 miles from Kahului to Wailea

Hotel Wailea and Wailea Beach

Landing at 10 p.m. anywhere—not just on Maui—is otherworldly. You can’t see anything, but you know you’re somewhere very, very far from home. Island tunes, heavy on the ukulele, warble through the radio speakers of our rental car as we drive off into the night on a strange island in the middle of the Pacific. It’s a half-hour drive south from Kahului Airport to Wailea, on the south shore, and there’s not another car in sight. Our first stop: Hotel Wailea, an adults-only, all-suite retreat hidden in the hills. We’re greeted with fresh leis, then whisked by golf cart to our suite—a serene space with travertine stone, white oak floors, a spacious kitchenette featuring Hawaiian Ohia wood cabinets, and private lanai where the following morning reveals a jaw-dropping view we couldn’t see the night before: a Zen-like oasis of flowerbeds, mango trees, and dead-on views of Lanai, Maalaea Bay, and distant West Maui.

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Hotel Wailea’s largest caveat is that it’s not on the beach—in fact, far from it, up on a hill—but there’s a certain kind of luxury to having a private Mercedes escort you personally down to the sand. Any first day in Hawaii should involve soaking in the sun at length. When it’s time for lunch, you’ll not lack for options: Wailea Beach is lined with fabulous resorts (and restaurants) including the Four Seasons and Grand Wailea, where Bistro Molokini serves up tropical cocktails, small plates including juicy fish tacos, and from your table, the perfect vantage point for watching humpback whales breach offshore.

Dinner is best had back at the hotel, timed with the sunset. Ask for a table on the terrace, where you can watch the sun slip slowly beneath the water as you dig into sublime seafood platters like the crudo board and the cioppino (fish stew), paired with a glass of Sancerre. We take our time finishing it as the sky darkens and attendants light torches along the pathways below. There isn’t room for dessert, but I’m not sad: our wake-up call tomorrow is 4 a.m.

Days 3-5: Drove 115 miles from Wailea to Ka’anapali via Haleakalā National Park

Haleakalā National Park

It’s a strange sensation, pining for the coldest place on Maui. Yet that’s exactly why, on just our second day, we get up before dawn: to see the sun rise from the 10,023-foot summit of Haleakalā National Park. It’s an hour-and-a-half drive from Wailea, and our tiny rental car groans with displeasure as we scale the dormant volcano, rounding steep hairpin turn after steep hairpin turn in the pitch dark. The summit itself is packed with photographers and other early-risers bundled and huddled together. (Yes, there are places in Hawaii where you’ll be grateful for gloves and a down jacket.) But as the sun breaks the horizon, the liquid sky transforming from navy to lavender to tangerine to white, our shivers are all but forgotten. The open volcanic landscape unfolds before you, rocky and red and barren. A park ranger chants in native Hawaiian. Various onlookers lower their cameras. The mountain’s sacred energy is tangible as a new day’s light spreads swiftly across the island. Haleakalā means “The House of the Sun.” It’s worth flying halfway across the Pacific to see.

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Visitors are welcome to extend their park stay and hike downward into the aeolian cinder desert, where trails crisscross craters and into the native shrubland. Budding botanists, look out for the rare and fascinating native silversword, found nowhere else on Earth.

Leoda’s Kitchen and Pie Shop

After making the slow descent into warmer weather, turn back towards Kahului at the mountain’s base and take the alternate road, Honoapiilani Highway, that winds up West Maui. To the right looms the West Maui Forest Reserve, with its steeply sloping (and impossibly green) ridge lines; to the left, camper vans line public beaches, where you can spot surfers carving the waves like pros. Eventually, you’ll arrive in Olowalu, a sparsely populated community and home to Hawaii’s most striking coral reef. Not to be missed: Leoda’s Kitchen and Pie Shop, the best brunch spot in town, beloved for its just-baked sweet and savory pies, loaded sandwiches and burgers, steaming biscuits, and fresh-squeezed lemonade and orange juice. It’s the perfect antidote for an early morning spent above the tree line. Thermal tote bags are also available for purchase, in case you want to save a bite or two for the road (trust me: you will).

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Ka’anapali and Sheraton Maui

Twenty minutes north of Olowalu, just past Lahaina, is Ka’anapali, a popular resort town home to Maui’s most famous beach. This wide, mile-long stretch of sand is lined with seven resorts, high-end shops, many of the island’s best luaus, and water both calm and clear—perfect for kayaking, snorkeling, and whale-watching. The Sheraton Maui is a standout for its clean-lined rooms facing the sea and prime beachfront beside iconic Black Rock, a stone jetty and Hawaiian sacred cultural heritage site that, legend says, King Kahekili of Maui dove off of to prove his spiritual bravery back in the 1700s. Each night at dusk, the hotel holds a cliff-diving ceremony that reenacts this ancient ritual. Even if you’re not a hotel guest, you can watch it unfold from Cliff Dive Grill as the sun slowly sets beside the distant island of Lanai.

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Photo courtesy of Starwood Corporate

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Star Noodle

The island sun will no doubt make you work up quite the appetite. As fans of Top Chef, my husband and I were dying to try Star Noodle, opened in nearby Lahaina by 10th-season contestant (and local boy) Sheldon Simeon. And it did not disappoint. Everyone raves about the steamed pork buns and garlic noodles, but we were blown away by the savory hapa ramen, ahi avo poke, and, to cap it off, sweet malasadas (a type of Portuguese doughnut popular in Hawaii) dipped in melted chocolate and butterscotch. Reservations for dinner fill up fast, so be sure to book a few days in advance.

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Photos courtesy of Star Noodle

Feast at Lele

Everyone knows no trip to Hawaii is complete with attending a traditional luau, a Hawaiian party usually paired with regional cuisine and entertainment such as music and hula. Maui has a handful of fabulous options to choose from, including the Old Lahaina Luau (the most authentically Hawaiian) and the Ka’anapali Beach Luau (great for families). The Feast at Lele, in Lahaina, is a favorite for romantics: guests are seated at private tables (as opposed to the traditional buffet-style dinner) and served beautifully plated courses while performances highlight the Pacific islands of Hawai’i, Aotearoa (Maori for “New Zealand”), Tahiti, and Samoa.

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Photos courtesy of Feast at Lele

Days 5-6: Drove 76 miles from Ka’anapali to Hana

Road to Hana + Wai’anapanapa State Park

It’s time to strike out east—what many visitors (and most locals) consider the true side of Maui. Rugged and remote, East Maui is a slice of Hawaii frozen in time, where life moves slowly and the rainforest rules all. Little has changed in Hana, a pastoral small town untouched by development, for decades—the community is built around bungalows and anything you need will be found at the Hasegawa General Store, opened in 1910.

To get there, one must conquer the famous Road to Hana—a curvy coastal highway that winds through thick jungle, rife with hairpin turns, one-lane bridges, and incredible natural beauty. To drive straight through from Kahului takes roughly two hours, but many dedicate a lot more (in fact, expect to block off most of the day) as you’ll want to stop frequently at its many mapped-out sights along the way—cascading waterfalls, vast overlooks, family-run fruit stands. Just be sure to plan out your journey before departure, as many stops are flagged only by their mile markers.

One absolute must-see: Wai’anapanapa State Park, famous for its unique black-sand beach, freshwater caves, and surviving ancient Hawaiian sites including shelters and pictographs. It’s a popular place to swim, hike, and set up camp—a more adventurous option for those not looking to rent an Airbnb or splash out with a stay at (the albeit gorgeous) Travaasa Hana.

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Pipiwai Trail + Ohe’o Gulch

A 30-minute drive south of Hana takes you to Kipaluhu and the other side of Haleakalā National Park. Instead of volcanic rock, you’ll find a diverse, tropical rainforest filled with banyan trees, waterfalls, and more shades of green than you ever knew existed. Here, you can follow the idyllic two-mile Pipiwai Trail, a leisurely stroll across footbridges and through an immense and percussive bamboo forest (the stalks clink together with the breeze), to Waimoku Falls, which tumbles from a 400-foot sheer cliff face. By this point, we’ve lost count of how many waterfalls we’ve seen so far, but it’s worth mentioning that the novelty, especially for us New Yorkers, never fades.

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Before leaving the park, leave time to take the 0.5-mile Kuloa Trail to Ohe’o Gulch, also known as the Seven Sacred Pools. Here, a string of waterfalls feeds tiers of pools until reaching the ocean—a popular attraction where a few brave souls (including us, with GoPro in hand) cross a field of slick, mossy boulders for a chilly swim.

Day 7: Drove 62 miles from Hana to Kahului via Kaupo

Piilani Highway

After spending time in Hana, visitors often retrace their route back along the Hana Highway. Instead, per a local’s recommendation, we opt to take the less-trodden southern road. It’s rocky and unpaved in places, but far more manageable in terms of visibility. The lush rainforest this is not: instead, you’ll pass miles and miles of open country along the back side of Haleakalā, where rolling grasslands are broken up every so often by the sight of roaming cows, gutted trucks, off-grid farms, and secret beaches. You might pass—at most—another car or two, but for the rest of the journey, it’s just you, the road, and a piece of Maui few ever take the time to see.

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