A Hawaiian Islands Hiking Overview

Hawaii is more than just beaches and Mai Tais — it's also a hiker's paradise. Each of the six accessible islands offers its own unique flavor of trails. And while some boast more quantity or variety, every island showcases natural beauty that’s sure to resonate with any outdoor lover. In this post, I share my impressions of each island and highlight my favorite trails from my time living and exploring in Hawaii.

Maui ("The Valley Isle")

Highest Peak: Haleakalā, 10,023 feet (3,055 meters)

Land Size: 727 sq miles (1,884 sq km)

SS Favorite Trails: Sliding Sands Trail, Waihe'e Ridge Trail, Pipiwai Trail

For many first-time visitors, Maui is the go-to island. It’s easy to see why. Its blend of pristine beaches, lush rainforests, and volcanic terrain draws travelers from around the globe.

At the heart of the island is Haleakalā, a massive dormant volcano rising above the clouds. Its summit feels otherworldly — a lunar-like landscape that also happens to be one of the best places on earth for stargazing. Maui also delivers with natural wonders like the lush Iao Valley and the famously scenic Hana Highway, packed with waterfalls, jungle, and dramatic coastlines.

While Maui doesn’t have the largest trail network, the hikes it does offer are incredibly diverse. Haleakalā National Park features trails that wind through volcanic craters and along alpine ridges. The Pipiwai Trail, one of my personal favorites, cuts through a towering bamboo forest on its way to the 400-foot Waimoku Falls. For a taste of the island's volcanic past, hikes to Red Sand and Black Sand Beach deliver both history and jaw-dropping views.

Hawaii ("The Big Island")

Highest Peak: Mauna Kea, 13,803 feet (4,207 meters)

Land Size: 4,028 sq miles (10,423 sq km)

SS Favorite Trails: Mauna Kea, Pololu Valley, Kilauea Iki

As the name suggests, the Big Island is the largest in the Hawaiian chain, and also the youngest. It’s a land of contrasts, home to active volcanoes, snow-capped peaks, lava deserts, and lush valleys.

Its centerpiece is Volcanoes National Park, where Kilauea continues to shape the landscape with real-time eruptions (if you're lucky with timing). The island also features the arid Kona Coast, the lush Hamakua Coast, and Mauna Kea, a massive dormant volcano whose summit rises above the clouds and is technically the tallest mountain in the world (measured from the ocean floor that is).

Hiking here is incredibly varied. You can explore the steaming crater trails around Kilauea, or venture north to rainforests and waterfalls. The Pololu Valley Trail offers sweeping views of the Kohala coastline and a dramatic descent to a black sand beach. For those seeking altitude, the Mauna Kea Summit Trail is a must-do, delivering panoramic views and a true alpine experience, something few associate with Hawaii.

Kauai ("The Garden Isle")

Highest Peak: Kawaikini, 5243 feet (1,598 meters)

Land Size: 532 sq miles (1,378 sq km)

SS Favorite Trails: Awa'awapuhi Trial, Kuilau Trail, Hanakapi'ai Falls

Kauai is a dream for nature lovers — a misty, green jewel that feels almost untouched. With fewer developed areas and a more tranquil atmosphere, it’s the perfect place to get lost in lush valleys, towering cliffs, and secluded beaches.

The island’s most iconic feature is the Na Pali Coast, where razor-sharp cliffs plunge into the Pacific and narrow valleys hide secret beaches. Equally stunning is Waimea Canyon, often called the “Grand Canyon of the Pacific,” with its red rock gorges and verdant ridgelines.

From the famous Kalalau Trail to lesser-known jungle paths, Kauai offers some of Hawaii’s most rewarding hikes. Whether you’re climbing ridge trails with sweeping ocean views or following rivers to waterfalls deep in the jungle, the island delivers unmatched natural beauty.

Oahu ("The Gathering Place")

Highest Peak: Mount Ka'ala, 4,025 feet (1,227 meters)

Land Size: 596 sq miles (1,544 sq km)

SS Favorite Trails: Three Peaks, Koko Crater Rim Trail, Kuli'ou'ou Loop Trail

Oahu was my home for five years, and while it’s often associated with urban sprawl and heavy tourism, it has a wild side that’s often overlooked.

Yes, Oahu has Honolulu, Waikiki Beach, and Pearl Harbor. But beyond the traffic and tourists lie two rugged mountain ranges, the Ko'olau and Waiʻanae, and a wealth of waterfalls, ridgelines, and crater hikes.

Oahu easily has the greatest quantity and variety of hikes. Crater climbs like Diamond Head and Koko Head offer quick hits with great views. Trails like Manoa Falls and Waimano Falls bring you into rainforest settings. And for those who want a little adrenaline, the island’s raw ridge hikes deliver, with knife-edge paths and 1,000-foot drop-offs that will test your nerves. In short, Oahu may be crowded, but it’s still a hiker’s paradise.

Lanai ("The Pineapple Isle")

Highest Peak: Mount Lānaʻihale, 3,366 feet (1,026 meters)

Land Size: 140 sq miles (362 sq km)

SS Favorite Trails: Pu'u Pehe (Sweetheart Rock), Koloiki Ridge Trail

Lanai is Hawaii’s most exclusive island — tiny, quiet, and 98% owned by tech billionaire Larry Ellison. But beyond the luxury resorts lies a rugged, off-the-beaten-path hiking experience.

The island’s landscape is dry and windswept, with places like the Garden of the Gods offering a Martian-like view of twisted rock and red soil. While there’s no rainforest here, there’s solitude and beauty.

Hikes are fewer but worthwhile. The Munro Trail leads to Lānaʻihale, the island’s highest point. Shoreline hikes like Pu’u Pehe offer stunning coastal views. Just make sure you’ve got a 4x4 as many trailheads require navigating rough, unpaved roads.

Molokai ("The Friendly Isle")

Highest Peak: Kamakou Peak, 4,961 feet (1,512 meters)

Land Size: 260 sq mi (673 sq km)

SS Favorite Trails: Kalaupapa Trail, Halawa Falls Trail

Molokai feels like a step back in time. With only about 8,000 residents, it’s the least developed of the main islands and fiercely protective of its culture and traditions.

Molokai’s north shore boasts some of the tallest sea cliffs in the world. The island is also home to Kalaupapa, a remote peninsula with a tragic and powerful history, only accessible by small plane or a steep, winding trail.

While much of the interior is off-limits, what is accessible is magical. The Kalaupapa Trail descends over 2,000 feet to the old leprosy colony and offers unforgettable views along the way. In the east, the Halawa Valley Trail takes you through taro fields and jungle to twin waterfalls. Hiking here is as much about solitude and spirituality as it is scenery.

SS Final Thoughts

I still believe Hawaii is the most beautiful place on Earth. And hiking is hands down the best way to experience its raw beauty. I feel lucky to have spent five years exploring all six of these islands and getting to know their unique trails, landscapes, and personalities.

My hope is that this post gives you a sense of just how different each island is. But really, the only way to understand their magic is to hike them yourself.