Top trails on Maui, Lanai, and Molokai

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Going off-road on the islands that make up Maui County

Whether ziplining among the forest on Maui, sailing around the island of Lanai, or flying along Molokai’s epic sea cliffs, there are a lot of ways to discover the three major islands that comprise Maui County: Maui, Lanai, and Molokai. 

As avid hikers, we believe one of the best ways to uncover the islands’ many secrets is to get off of the beaten path and explore on foot. With so many amazing trails from which to choose, it was not easy to come up with one favorite hike from each island, but we’ve provided a selection that should suit a wide range of tastes.

Lanai’s Munro Trail

Our favorite hike on Lanai is a 13-mile extension of the Munro Trail; let’s call it the Munro Trail Plus. The full-day trek begins at the bucolic Four Seasons Resort Lanai, The Lodge at Koele (check in here before you start your hike) and ends at the blissful Four Season Resort Lanai, Manele Bay.

Deep grooves in the red earth let you know that you are on the right path, as this trail also serves as a road for ATVing. The scent of eucalyptus heightens your senses as you climb 1,600 feet and amble beneath the stands of Norfolk Pines that George Munro once planted here to coax water from the low clouds and irrigate the arid island.

Viewfinder Tip: Hiking at dusk or dawn is especially rewarding in Maui County as the lighting is almost other-worldly.

Along the way, make sure to pause at Lanaihale, Lanai’s highest peak, before the long, gradual descent toward the ocean. You’ll be treated to awe-inspiring views of Maui, Molokai, Kaho’olawe, The Big Island, and Oahu.

Once you arrive at Manele Bay, make sure to let the staff know you made it safe and sound. If you are staying at either Four Seasons property, you can grab a towel, order a cocktail, and rest your weary legs poolside. You earned it (and the shuttle ride back to the Lodge at Koele).

Summitting the volcano on Maui

Haleakala National Park offers more than 30 miles of hiking trails, from strolls through dense, percussive bamboo forests near the ocean to treks across the volcano’s rust-colored, lunar-like summit.

One of the most popular hikes in the park is a descent into the center of the sleeping volcano’s caldera. The 2.5-mile hike takes you right into the birthplace of Maui, through clouds that stack up in the crater, mimicking smoke. Silver sword plants make their home here, letting you know that this seemingly barren landscape is very much alive.

The weather at the top of Haleakala is something that takes most visitors by surprise. While the coastal portion of Haleakala National Park enjoys nearly perfect, barely fluctuating tropical weather, the volcano summit is a completely different story. High above the clouds, the weather can drop below freezing at any time of day. Be prepared!

Hiking Maui

Molokai history on the Kalaupapa Trail

If you plan it right, your flight into Molokai will skirt the island’s north side and provide you with stunning views of the world’s tallest sea cliffs. These are the kind of natural wonders of which myths are made; hero’s journey obstacles that taunt visitors to test their mettle. The 3.2-mile Kalaupapa Trail allows you to do test your mettle, too.

While many visitors opt to ride mules down the Kalaupapa Trail, we recommend conquering the sea cliff on foot. The steep trail descends 1,700 feet via a series of switchbacks like zigzag stitches that ar holding together the two halves of the island. Each of the 26 switchbacks is numbered in case you are so mesmerized by the ocean views that you forget how far along you’ve come.

The price of the hike (this is private land) includes a tour of the small colony of Kalaupapa and powerful insights into the lives of the area’s residents; a population of individuals once quarantined for suffering from Hansen’s Disease. There is something incredibly empowering about taking on the precipice that once served as a barrier and now offers a route to understanding and compassion. We can’t wait to do it again.

What kind of hikes are most appealing to you?

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Kent and Caanan are self-described fulfillment fanatics who rejiggered life so that every day could be a dream day. They started a virtual consulting business (specializing in helping individuals and organizations navigate change) in order to see the world, give back, and make a living from anywhere while doing work they love. On the side, they share their adventures by writing about LGBT getaways, nature-centric journeys, the tech side of travel, globetrotting with purpose, and luxury escapes that aren't fussy.

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