About Me/This Blog

My name is Steve and I moved to Oahu in April of 2016, a time when my life was not in a good place. Then I discovered the wonders of hiking on Oahu and Hawaii and the incredible joy and beauty that comes with it. This is what inspired me...


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© 2019 The Hiking HI LLC

Advanced Hikes

For experienced hikers only. Your body will hurt after you are done with these hikes. They will challenge you physically, technically, or both as you tackle trails most wouldn't even consider. Narrow ridges, tough rock scrambles, and overgrown trails are commonplace on these hikes. However, the views and sense of accomplishment you will have once you are finished will make it all worth it.

March 4, 2019

Difficulty: ADVANCED

Time: 8+ HOURS

Distance: 12 MILES

Elevation Gain: 1800 FEET

Foot Traffic: LOW

Challenges: Overgrown, Muddy, Narrow Ridges with Steep Dropoffs, Shadeless

Sights: Stairway to Hell, Windward Side, Honolulu

What to Bring: Sunscreen, Long pants and sleeves, Water (>2L), Lunch

The lesser known of Oahu's staircases, the hike nicknamed "Stairway to Hell" is just like it sounds--- an old sketchy set of abandoned stairs tha...

January 7, 2019

Difficulty: ADVANCED

Time: 5-6 HOURS

Distance: 5.5 MILES

Elevation Gain: 1900 FEET

Foot Traffic: LOW

Challenges: Narrow Ridges, Overgrown, Potentially Muddy, Rock Scrambling and Free Climbing 

What to Bring: Water, Snack/Lunch, Long Pants

Sights: Windward Side, Makaua Falls, Kahana Valley

A fun and challenging hike on the windward side of Oahu, Kahekili Ridge has a little bit of everything. Challenging climbs and scrambles, narrow rid...

December 6, 2018

Difficulty: ADVANCED

Time: 7+ HOURS

Distance: 12 MILES

Elevation Gain: 2400 FEET

Foot Traffic: LOW

Challenges: Overgrown, Muddy, Some Narrow Ridges

Sights: Honolulu, Windward Side

What to Bring: Water (>2L), Sunscreen, Snack/Lunch, Long Sleeves/Pants

A difficult ridge hike near Honolulu, this ridge takes you up one of the Ko'olau finger ridges to the Ko'olau Summit Trail. You will be challenged with brush, mud, narrow ridges, and even...

September 4, 2017

Difficulty: ADVANCED

Time: 7+ HOURS

Distance: 12 MILES

Elevation Gain: 4500 FEET

Foot Traffic: LOW

Challenges: Altitude Sickness, Endurance Challenge, Possible Freezing Temperatures

Sights: Mauna Loa, Lake Waiau, Observatory, Mauna Kea Summit

What to Bring: Good Hiking Shoes, Lots of Water, Lunch, Cold Weather Gear, Sunscreen, Aspirin

The tallest peak in all of Hawaii and the tallest sea mountain in the world, hiking to the summit of...

July 24, 2017

Difficulty: ADVANCED

Time: 5-7 HOURS

Distance: 4 MILES

Elevation Gain: 1900 FEET

Foot Traffic: LOW

Challenges: Steep climbs, Rock Scrambling on Narrow Ridges, Overgrown, Muddy

Sights: Ko'olau Mountain Range, Kahana Valley, Windward Coast

What to Bring: Lots of Water, Shoes to get muddy, Long sleeves/pants, Sunscreen, Snack/Lunch

Pu'u Manamana has a reputation for being one of the more dangerous hikes on Oahu. You are required to trave...

July 17, 2017

Difficulty: ADVANCED

Time: 6+ HOURS

Distance: ~5 MILES

Elevation Gain: 1900 FEET

Foot Traffic: VERY LOW

Challenges: Finding Trail, Narrow Ridges, Steep Climbs, OVERGROWN!!!

Sights: Pu'u Hapapa, Mount Ka'ala, Western and Central Oahu, Honolulu

What to Bring: Lots of Water, Food/Lunch, Sunscreen, Long Sleeves and Long Pants

At just over 3500 feet, Pu'u Kalena is the second tallest peak on Oahu. Not only are you required to gain nearly 2...

June 4, 2017

Difficulty: ADVANCED

Time: 7-9 HOURS

Distance: 8 MILES

Elevation Gain: 2200 FEET

Foot Traffic: MODERATE

Challenges: Getting to the stairs, Very Muddy, Steep, and Narrow Ridges

Sights: The Stairs, H3 Highway, K-Bay, Moanalua Valley, Ko'olau Mountain Range, Pearl Harbor

What to Bring: Lots of Water, Sunscreen, Good Shoes, Headlamp, Snacks/Lunch

An alternate route to the famous Stairway to Heaven Hike, this path is half as illegal... but...

April 9, 2017

Difficulty: ADVANCED

Time: 1-2 HOURS

Distance: 1 MILE

Elevation Gain: 800 FEET

Foot Traffic: LOW

Challenges: Steep incline with loose rocks, Narrow ridges with steep dropoffs, Difficult free climbing

Sights: Kailua, Kaneohe, K-bay, Three Peaks, Pali Lookout, Ko'olaus

What to Bring: Shoes with Good Grip

A name that is notorious on Oahu, this hike is as beautiful as it is dangerous. The hike starts at the popular Pali Lookout where you...

March 12, 2017

Difficulty: ADVANCED

Time: 4-5 HOURS

Distance: 4.5 MILES 

Elevation Gain: 1650 FEET

Foot Traffic: HIGH

Challenges: Rock scramble, Free climbing, Steep and narrow ridges

Sights: The Peaks, The Mokes, K-Bay, Ko'olaus, Makapu'u

What to Bring: Water, Sunscreen, Snack, Shoes with good grip

Despite its popularity, Three Peaks is one of the more challenging and dangerous hikes on the island (assuming you go to all three peaks). It's a long s...

February 19, 2017

Difficulty: ADVANCED


Distance: 10 MILES LATERAL (from Kuilau Ridge Trailhead)

Elevation Gain: UNKNOWN

Foot Traffic: VERY LOW

Challenges: Unmarked trail, River crossings/rock hopping, High flash flood potential, Overgrown, Muddy, Some steep climbs

Sights: Gate to Jurassic Park, Guardian Falls, The Weeping Wall (if you find it)

What to Bring: Full day of food, Lots of water, Sunscreen, Shoes you can get wet, Guide/Someone...

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