Vacationing in a lush, tropical island paradise this year means plenty of beach time, but don’t miss the opportunity to explore. Take a much-needed break to a place full of sand, sun, fun, and plenty of rest and relaxation. You’ll want to lace up your hiking shoes and find some hiking trails on Oahu beyond the beach, where you can explore even more of Oahu’s natural beauty.

Diamond Head (Leahi) Trail

Possibly the most iconic volcano in the region, the trail to the summit of Diamond Head near Waikiki was forged as part of the U.S. Army Coastal Artillery defense system in 1908.

The trail is inside the Diamond Head State Monument, which is a one-way 0.8-mile (one-way) trail that boasts a 560-foot elevation change from the crater floor. The out-and-back hike takes approximately two hours for a safe and leisurely round-trip.

Be prepared for uneven ground and steep terrain, with tunnels and military bunkers that will payout 360-degree views of Waikiki, Honolulu, and the surrounding area is worth the effort.

Reservations are required to visit, and parking is available in two-hour slots starting at 6 a.m.

Waimea Valley Trail

Coming to one of our favorites, Waimea Valley on Oʻahu’s North Shore is an amazing botanical garden with over 5,000 plant varieties, Hawaiian cultural sites, and rare birds like peacocks. We really love the sweeping view of the greenery around here.

Hiking on the Waianae mountains is low-impact. When you follow the paved path, it will lead to Waihi Waterfall and back, making for a great round trip and swimming opportunity. The waterfall has a lifeguard and a natural pool that’s perfect for a mid-hike swim.

There’s a Visitor Center where you can learn about the trail while stopping by and grabbing something to eat. If you visit on a Thursday between 2:00 and 6:00 p.m., you can also check out the Haleʻiwa Farmers Market. Entrance is $16 per adult and $8 per child, so plan accordingly.

Koko Crater Trail

The railway “stairs” hike is a short drive from the Diamond Head and Waikiki area. The tough, extremely inclined 2.8-mile out-and-back climb results in reaching the summit of the Koko Head Crater.

The military constructed the railway to transport supplies to soldiers during World War II, and the site had many other functions until it was given to the City of Honolulu and became Koko Head Regional Park.

You’ll experience a 990-foot elevation change that brings you 1208 feet above sea level. Count the railroad ties as you go and find there are 1,048 before another 30-foot climb to the lookout area.

The trailhead is in Koko Head District Park. Just a heads-up: The parking lot is closed overnight, so it’s better to check the opening hours and then arrive.

Makapu’u Point & Lighthouse Trail

For breathtaking views of Oahu’s southeastern shoreline, including tall sea cliffs looking out to the blue ocean beyond, this trail is for you.

The trail is situated off of Kalanianaole Highway on the southeastern tip of the island about 12 miles east of Honolulu. Makapu’u is a remnant of a volcanic ridge that rises over 600 feet from sea level.

The lookout boasts panoramic views off Manana Island and Black Rock Island, vast ocean views, as well as views of neighboring Molokai and Lanai.

If you are an animal lover, you shouldn’t miss this hike! It’s a great spot for spotting a variety of seabirds and whales during the season, that is, in the winter months, from December to April.

During our hiking session, we saw many families coming together with their kids and also people of different age groups, so yes, it’s a great family-friendly activity. The hike is on a short hike on a paved trail that’s easy to navigate with strollers, making it easy for all.

Kuliʻouʻou Ridge Trail

The 4.4-mile round-trip trail is a short drive from Waikiki, with the trailhead located at the end of Kalaau Place. The moderately challenging trail features stairs that make it easier to climb in some areas.

We enjoyed the Kuliʻouʻou Ridge Trail because it required some time, but the journey through dense woodlands was worth it. The sweeping over Oʻahu’s east side doesn’t show up until the end, but the hike through the rainforest in the heart of Oahu gave us amazing views of the island’s western half.

On your way through the diverse landscape, keep your eyes peeled for a variety of plants and trees. The trail ends at a final plateau boasting breathtaking views of East Oahu. Schedule about four hours for the hike. Don’t forget to wear proper footwear, as the hike can get quite slippery sometimes.

Kaiwa Ridge Trail (Lanikai Pillbox Hike)

Also known as the Lanikai Pillbox, this is an intermediate hike. The trail is a great way to test your skills at an intermediate level of difficulty. The climb starts just above Lanikai Beach and is steep throughout.

The 90-minute round trip offers scenery and breathtaking views, whether or not you opt to extend your trip another hour along the ridge. The payoff at the trail’s end is stunning views of the island’s windward side, including the Mokulua Islands, Kailua Beach, and Lanikai Beach.

When parking in the Lanikai neighborhood, be sure to adhere to the posted signs, as enforcement is strict.

Ehukai Pillbox Hike

Get a great view of the crashing waves of Oahu’s North Shore, as well as the Seven Mile Miracle. The 1.5-mile out-and-back trail is a good 90-minute hike.

The trailhead is right next to Sunset Beach Elementary School, across from Ehukai Beach Park. This hike is mostly reserved for expert hikers, as there are severe inclines at various places throughout the trail.

Walking this trail is a serious physical challenge. Those weak knees, hearts, or any other physical challenges are encouraged not to take this trail. Those who can will be rewarded with views of the Banzai Pipeline and Sunset Beach.

Manoa Falls Trail

Great for hikers of all skill levels, the trail is more of a “walking” trail than a “hiking” trail. The 1.6-mile round trip has a slight uphill grade that kids and beginners will negotiate fairly easily.

The trailhead is located a quick 15-minute drive from Honolulu, where you’ll be transported to the lush, tropical views of lush Manoa Valley – a truly different world.

The location features massive century-old trees and a lush bamboo forest. It has also been a popular spot for TV shows and movies, like Jurrasic Park.

The trail is said to receive consistent rainfall throughout the year, making it often muddy. Therefore, appropriate footwear and bug spray are a must. Although the trail is short, the waterfall will make it worth the walk. Just note that you can’t swim!

Aiea Loop Trailhead

It’s another trail on the list for beginner hikers. The less than five-mile hike is shaded with flat pathways along the looped trail. Take in the beauty of native trees, lemon eucalyptus grove, Norfolk pine, native koa, and ʻōhiʻa trees.

Located on the west side of the Hālawa Valley, you’ll have great views of places like Pearl Harbor, Diamond Head Crater, and the Ko’olau Mountains from the ridge.

Olomana Trail

If you’re looking for sweeping views from the mountain, Olomana Trailhead is the place to go! You can climb up three steep peaks, offering a sense of satisfaction and expansive views of the island.

This challenging trail climbs nearly 2,000 feet to reach the first of three peaks overlooking Windwardside.

The first two peaks are safe to climb. The views from the first peak, along with the second one, provide impressive views of the Koʻolau range and the coastline. The third peak, however, is quite dangerous, so we don’t recommend anyone to climb it.

You won’t find parking available at the trailhead for this hike. We suggest you park on Auloa Street and then walk down Loop Drive to reach the trailhead.

FAQs

What should I bring when hiking on Oahu?

When hiking the trails, it is essential to bring plenty of water (at least one liter per person) and snacks for the way. Also, carry sunscreen, a hat, sturdy shoes, mosquito repellent, and a fully charged phone. Also, first aid kit and a trail map are also recommended.

When is the best time to hike in Oahu?

We usually prefer hiking in the mornings as it generally offers cooler temperatures and clearer skies. Avoid hiking during peak midday heat, especially in summer months.

Are there guided hiking tours available on Oahu?

Yes, several companies offer guided hiking tours on Oahu. These tours provide insights into local flora, fauna, and history while ensuring safety.

Hiking on Oahu

Rest and relax after a hike on one of Oahu’s best hiking trails in a vacation rental by Midway Vacations. From a cozy studio for a solo or sweetheart escape full of hiking exploration to a two-bedroom for you and even more of your loved ones, we have a cozy vacation rental that’s just right for your tropical island trail hike.

Arrive and feel the stresses and worries of home melt away, replaced by the spirit of Aloha. Prepare trail snacks or any other meal of the day in a fully equipped kitchen, relax in an open living space, or retreat to a private bedroom.

Contact us today to start planning your Oahu hiking adventure!