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10 Best Hikes on Oahu Island

Hiking trail in Oahu
May 17, 2022

Ready for a little adventure? Let’s go! Whether you are wanting to get the kids’ energy out, see some of the spectacular Oahu waterfalls, or really challenge yourself – we mean this in the best way possible – take a hike! Below are Best Western The Plaza Hotel’s top 10 choices for hikes during your vacation in Oahu.

Don’t forget your camera!

A simple look out the window proves Oahu has no shortage of beautiful scenery. And, a little additional effort going on one of the below hikes will only increase the awe and wonder provided by Oahu. These are the hikes that create photographs you will be reminiscing over for years, not to mention will get you the likes on your social media account that will invite envy and curiosity. 

Diamond Head State Monument

1.6 miles - Beginner - Great for families! 

A family vacation to Oahu is simply not complete without a trip to Diamond Head State Monument. The monument was formally a defense artillery operated by the US Army, and now is a popular spot for families to climb the steep summit and be rewarded for expansive 360-degree views of Oahu. At the peak you can see the Hawaiian islands Maui, Molokai, and Lanai.  Bring snacks or a picnic to linger after your hike. You may be lucky enough to spot a notorious Hawaiian resident, the mongoose.  

Makapu’u Point Lighthouse 

2 miles - Beginner - Great for families 

This hike is great for everyone in the family and can be accomplished in around 30 minutes. The views of the shoreline and Makapu’u Point Lighthouse are exceptional and perfect for a family photo, so pack that selfie stick. Makapu’u Point Lighthouse is located on a volcanic ridge that is perched 600 feet above the ocean. On clear days, you can not only see beautiful coastlines and the clear blue water Hawaii is famous for, but also the Hawaiian islands Molokai and Lanai. There is very little shade, so bring sunscreen and a hat!

Kaneohe Bay Pillbox

1.8 miles - Beginner/Intermediate - Great for families! 

This hike is suitable for beginners and families, albeit with some stamina as there are steep inclines. This trail is another Oahu site named after former US Army bunkers. Take in the history and the views! The short hike provides beautiful ocean views. From the top of the pillbox you are rewarded a view of he Koʻolau coast, Kailua beach, Lanikai beach, and Waimanalo beach.

Koko Crater Railway Trail

1.8 miles- Intermediate/Advanced 

All aboard! Don’t be surprised by “railway” in the title, this hike packs a punch and will be a challenge even for those who never miss their morning workout. So, don’t bring your little ones! The railway was a relic of World War II, constructed to provide supplies to the US Military. The tough 990 foot incline up 1,048 railway stairs leads you to view the magnificent Koko Crater. You will sweat, but the view will be worth the breathtaking views. Bring water, sunscreen, and a hat. 

Olomana Three Peaks

4.4 miles- Advanced

Another advanced hike for the adventurous at heart. This trail leads you up three peaks while you gain nearly 2,000 feet in elevation and offer a view of the coast and Ko’olau range. Hikers looking for a sense of accomplishment and arguably the best mountain views in Oahu should not miss out on Olomana Three Peaks. 

Mt Olympus 

5.2 miles - Advanced 

A 5.2 mile climb up Mt Olympus is like what it sounds like…demanding, exciting, and awe-inspiring. Climb 2000 vertical feet with the assistance of ropes where things get slippery and be rewarded with beautiful valley views that leave you feeling like an olympian. 

Do go chasing waterfalls! 

One of the most magical parts of Oahu are the magnificent waterfalls. It is a special moment when you start to hear the power of Hawaii’s waterfalls before you even see them. We want the moment you arrive to see your first Oahu waterfall to take your breath away. We recommend Manoa Falls Trail or Maunawili Falls Trail for an unforgettable Hawaiin waterfall experience. 

Manoa Falls Trail 

1.6 miles - Beginner - Great for families 

Those who only packed flip flops need not be deterred by this hike. This Oahu must offer gorgeous, lush jungle-like scenery and an easy 1.6 mile, mostly shaded stroll, gifts you one of Oahu’s many magnificent waterfalls. The 150 foot Manoa Falls waterfall will leave you with the feeling of peace and serenity you traveled for. 

Maunawili Falls Trail

2 miles - Intermediate/advanced

The hike is technically only two miles but give yourself two hours as there aere are large steps, streams, and boulders to navigate. A worthwhile investment once your arrive at the gorgeous 20 foot waterfall and cool, natural pool. 

Wear a swimsuit!

Sure you can always lounge by the Best Western pools and or one of the many gorgeous Oahu beaches, but there is something especially satisfying about hiking to a hidden natural pool. 

Waimea Falls 

1.9 Miles - Beginner - Family friendly 

A visit to Waimea Valley is a must and this shaded, paved, beautiful, this trail is great for everyone! A breezy 1.9 walk ends at a 45-foot waterfall with swimming maintained by lifeguards who even offer life jackets for those who want them. Plan to spend a while relaxing on the rocks, swimming, or snacking. There is an entry fee and a cafe nearby in case you want to stay for lunch. 

Waimano Pool Trail 

2.9 Miles - Intermediate/Advanced 

For a more challenging venture to a swimming hole, check out Waimano Pool Trail, an at times muddy adventure that leads to two natural spring pools, one with a rope swing! Sure it’s a challenge, but a challenge that ends in a treat!  We recommend water shoes with good grip and hiking clothes that are swimmable that you don’t mind getting a little mud on. 


We rate our recommended hikes in general terms and, as with any outdoor activity, one should be aware of their own limitations and abilities before attempting. Please be respectful of local residents when hiking. Don’t trespass, don’t park illegally, and don’t leave valuables in your car. Bring plenty of water and snacks on the trail, wear proper footwear, and watch the weather, as conditions can change rapidly (we recommend always bringing a rain jacket).

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