top of page

Island Living Homes | 2021 Oahu's Expert Hiking Trails

Father’s Day is right around the corner -- Why not give Dad the gift of adventure! Dads love to get outside, from camping excursions to fishing trips, to HIKES. Most dads jump at the chance to get outdoors, so here's a list of adrenaline pumping hikes for the skilled hikers in your life -- Mom's can join too ;-)


Warning, this is just a highlight post -- do your own research, read the rules and stay safe when attempting these tough Oahu hikes! They are no joke. Some hikes on Oʻahu should only be attempted by those who are in excellent physical condition and are steady on their feet.


1. Three Peaks/Olomana Trail | Difficulty: Hard | Length: 4.5 miles |Location: Kailua

A trail by this name was never going to be an easy hike, and this one totally isn’t. But if its adventure you want, then its adventure you’ll get! Olomana Trail is a 4.4 mile heavily trafficked out and back trail located near Kailua, that features a great forest setting and is only recommended for very experienced adventurers. You’re going to need some good upper body strength to haul yourself up, but just think of the satisfaction and the immense views across the treetops of Oahu when you do.

Olomana Trail Kailua
Three Peaks/Olomana Trail | Kailua

2. Tom Tom Trail | Difficulty: Hard | Length: 6.6 miles| Location: Honolulu

The Tom Tom Trail might not be one of the most well-known hikes on Oahu, but it’s one of the most spectacular. Beginning at the Makapu’u lookout, the path runs along a fence where you can come across for fairly amazing views of Oahu. The panoramic views over Makapu’u Lighthouse, the beaches of Oahu, and the deep blue ocean below are an absolute trea, the view quality/effort ratio is unmatchable on the island.

Tom Tom Trails Honolulu
Tom Tom Trails | Honolulu

3. Crouching Lion | Difficulty: Moderate |Length: 2.1 miles | Location: Haleiwa

Crouching Lion—near the community of Kaawa, Kaneohe and the magnificent Kahana Valley—offers up some panoramic delights. But that’s only after a steep and fairly challenging climb up the “Crouching Lion” itself. You’re only up a few hundred feet but you are looking straight down into the bay and at Kaawa. You will definitely work up a sweat as you climb over gnarled tree roots, and duck under stooping branches. Once reached the clearing take in the entire view, it is beyond beautiful.

Crouching Lion Haleiwa
Crouching Lion | Haleiwa

4. Ka’au Crater Hike | Difficulty: Hard | Length: 5 miles | Location: Honolulu

Literally about five minutes after you embark on this hike, you’re in a world of tall trees, vines and muddy trails, which makes this feel like a real adventure in a tropical island wilderness. The adventure is a long, but rewarding up-stream hike with three large, beautiful waterfalls and a hidden crater. Once you get to the top of the ridge you will have amazing views of the windward side of Oahu, Olomana, The Mokes and Chinamans Hat. The uneven terrain and the length of the hike make it a pretty strenuous journey, but well worth it!


Ka'au Crater Hike Honolulu
Ka'au Crater Hike | Honolulu

5. Ko'olau Summit Trail | Difficulty: Hard |Length: 0.7 miles | Location: Kaneohe

Is a 0.7 mile heavily trafficked out and back trail located near Kaneohe. The trail is primarily used for hiking and is accessible year-round. Its a great short hike, but do not let the length fool you- it is challenging! The panoramic vistas provided by this exposed trail are incredible, offering breathtaking views of O’ahu’s windward coast, from Kailua and Kane’ohe all the way to Kualoa. At the trail’s peak is the Pali Puka, a small “window” in the rock face of the mountain, said to be a hiding spot for Hawaiian warriors as they watched for approaching enemies.

Ko'olau Summit Trail Kaneohe
Ko'olau Summit Trail (Pali Puka) | Kaneohe

6. Pali Notches | Difficulty: Hard |Length: 7 miles | Location: Kailua

Short but intense hike! Known for being one of the most dangerous hikes on the island (* Attempt at your own risk, be extra cautious and wait for a fair-weather) but also one of the most impressive.You gain a lot of elevation quickly to reach the ridge, but the views of the windward side and the rest of the Ko'olaus are breathtaking. This narrow ridge hike requires you to rock climb over the man-made notches, which were supposedly created in the 1700's by King Kamehameha’s warriors to harbor cannons and warriors on lookout while they kept Nu’uanu Valley secure.

Pali Notches Kailua
Pali Notches | Kailua

Happy Father's Day, Super Dads of The World!

31 views0 comments


bottom of page