3 Breathtaking Hikes in Oahu, Hawaii

If you’d ask people to describe Hawaii and its 8 main islands in just two words you would get responses like “like paradise,” “gorgeous utopia,” “dream vacation” and even “life changing.” There is no where else quite like Hawaii. Hawaii is about 2400 miles from California and about 3900 miles from Japan. The shortest plane ride away is 5 and half hours to Los Angeles. Hawaii is the most isolated population hub in the world. From the different hikes, to waterfalls, to beaches, to rainforests, the canyons, the parks, to the exotic wildlife, the unique culture, the historical traditions and much more, the state of Hawaii is truly a breathtaking and unforgettable place. I had the privilege to go to Hawaii in May with my family and did several hikes with my brother while I was there. My favourite experiences in Hawaii were the hikes. Hiking gave me my idea of the “Hawaii experience.” Though I did complete more hikes in Oahu than what I’ve described these three hikes were my favourites!

Lanikai Pillbox Hike 


The Lanikai Pillbox Hike is just a 40 minute drive from downtown Honolulu or Waikiki Beach. The Lanikai Pillbox Hike is well known to be one of the easier hikes in all of Hawaii yet also one of the most scenic. Though the hike itself isn’t extremely challenging especially after the initial steep incline, I’d recommend bringing water and not wearing Birkenstocks, especially if you’ll hike it in the midday heat. After climbing the initial incline which only takes about 10 to 15 minutes you’ll get a breathtaking panoramic view of the stunningly blue Pacific and hundreds of palm trees that make up the beaches of Lanikai & Kailua.

As you approach and reach the pillboxes (which marks the end of the hike) there is a more elevated view of the Lanikai & Kailua beaches. There isn’t just an amazing view on the east side facing the beaches but an amazing view facing the west as well. On the west side there are incredible views of the mountains of central Oahu. All the greenery in the mountains, with the contrast of the beautiful clouds and the blue sky will leave you speechless.

Atop the Lanikai Pillbox (West Side)

When you finally reach the pillboxes and jump or climb on to them (somehow not managing to break an arm or leg on the way up) you’re greeted with one of the most beautiful views from anywhere in Oahu. There are no shortage of picture and video taking opportunities. Since this hike isn’t very challenging, it’s always busy and there’s opportunities to meet a lot of cool and interesting people from all over the world in different walks of life. (One of the coolest parts of travelling for me is meeting new people, hearing their stories and getting a new perspective.) This short but unforgettable hike isn’t daunting and should take between 60-90 minutes round trip with good shoes and being well hydrated. (There is no shade, the tropical Hawaiian sun is hot, especially in the afternoon, bring a hat and a lot of water.) The Lanikai Pillbox hike can’t be described in words or pictures, you’ll have to check it out yourself!

My brother sitting on the first Lanikai Pillbox overlooking the Pacific, the Mokulua Islands in the distance, Lanikai Beach and Kailua Beach.

Maunawili Falls Hike 

The Maunawili Falls Hike is a hiking trail about half way between Waikiki Beach and Kailua Beach in the middle of a wild and tropical Hawaiian range called Ko’olau. Trudging through the lengthy range takes you to an anticlimactic waterfall. Queue Jack Sparrow “it’s not the destination, so much as the journey they say.” Well that was off to a negative start, but I promise hiking to the Maunawili Falls is an amazing experience. Maunawili was much different than Lanikai, in that hiking to the Maunawili Falls didn’t have a picturesque fairytale ocean blue view and I definitely couldn’t have hiked it in my Birkenstocks. This hike is known to be challenging and for good reason. Hiking Maunawili, you really have to get down and dirty. 

At the start of the Maunawili Falls Hike there are several signs warning that the water or mud on the trail could be contaminated by leptospira causing leptospirosis. Leptospirosis is a disease caused by a bacteria found in infected rodents roaming the rainforest. (Maunawili just keeps getting better and better, I know.) Of course with my overly cautious personality, I trekked the first bit of the trail trying not to get any water or mud anywhere on my body whatsoever. I’d read about a lot of people’s ordeals with the bacteria and infectious disease. After a long half hour of frantically wiping my legs and arms if they came in contact with mud, I embraced the mud! When I finally let myself get down and dirty during the hike, was when the fun began. I realized shortly after the hike started that avoiding the mud and water would be mission impossible. Don’t be trepidatious about getting dirty to hike Maunawili because you will get very muddy and dirty very fast. There were several streams, ponds and inches of thick mud we had to trudge through to finish this hike and get to the waterfall.

The Maunawili Hike was the true Hawaiian wilderness “who knows what we’re going to see, hear or smell next” experience. Maunawili gives you a sense of real adventure, adrenaline and excitement which we’re all craving especially on vacation. The Maunawili Hike was long, scenic, tiresome, breathtaking, yet mentally and physically exhausting. There was a lot of climbing and descending, falling, crawling, ups, downs, and all arounds. There were points where you were forced to walk through water streams up to your knees (in your runners) and pull yourself up after falling in the mud. You were forced to navigate the trail by grabbing on to or stepping on branches, tree roots or rocks to keep your balance. There were other points where you would stop to question why you were hiking this muddy mosquito infested trail in the Hawaiian heat altogether. As the hike went on, especially when we were on our way back after seeing the waterfall, my mind kept thinking about how in just a few minutes I would be in an air conditioned car, on my way to Kailua Beach (one of my favourite beaches in the world) eating fruit and icecream, then once we got to the beach, I would be swimming in the Pacific. Finishing the Maunawili hike was mentally and physically exhausting yet also extremely rewarding. It was an incredible adventure.

Maunawili Falls, Oahu, Hawaii
My brother & I, Maunawili Falls Hiking Trail, Ko’olau Range, Oahu, Hawaii

My brother and I definitely aren’t normally very outdoorsy. Born and raised in a big city and not spending a ton of time outside of the city growing up, we definitely hadn’t had a hiking experience like the Maunawili Falls Hike before. In order to get through this hike together, we needed a lot of patience, motivation and determination to get through it. The mud was what really caused the frustration in completing this hike as it is only just a 2 mile hike and generally isn’t a very steep hike. Just ploughing through and maintaining good agility got us through. Again though it was tiring, it was still an unforgettable adventurous sibling bonding experience.

Koko Head Crater Railway Trail


Koko Head of all the hikes I did during my 2 weeks in Hawaii was my favourite. Koko Head is a daunting 1,050 steps that reaches an elevation of about 1,200 feet at the summit. Koko Head is a strenuous hike with a quick, sudden and steep incline. Koko Head’s steps are made up of an abandoned railway track. My brother and I did the Koko Head hike in time so that we could watch the sunset from the top.

Koko Head Crater Railway Trail, Oahu, Hawaii

Though Koko Head was extremely exhausting, the time of day we did the hike, the temperature and the breeze made the hike bearable. With a lot of water and adequate amount of determination you’ll find this hike breathtakingly beautiful the whole climb. The railway track path, climbing through the old railway tracks and the view the entire hike was absolutely surreal. I took frequent breaks on my way up (to relish in the beauty around me, just kidding because I was out of breath every 30 steps.) Though I did take frequent breaks, as soon as we acquired some elevation, I couldn’t believe the beauty I was surrounded by. Sitting at the top of the crater with views in every direction of south Oahu is truly mind blowing. Feeling the breeze, feeling the difficult but rewarding workout and exhaustion in every muscle of your body, feeling relaxed seeing views of downtown Honolulu and Hanauma Bay you really get a taste of the beautiful world we live in. I can’t describe it. Queue Louis Armstrong “and I think to myself, what a wonderful world…”

Summit of the Koko Head Crater Railway Trail, Oahu, Hawaii
Summit of the Koko Head Crater Railway Trail, Oahu, Hawaii

Have you been hiking in Oahu? What were your favourite hikes? I’d love to hear from you! Also if you liked this post please feel free to check out a couple of videos I made about my Hawaiian adventure!


  1. […] This year my family had the great privilege of spending 3 weeks in Oahu, Hawaii. Do I need to explain? Hawaii is the definition of paradise, breathtaking, colourful, beautiful and honestly magical. Being able to spend this time exploring such a beautiful party of the world with an insane amount of history, an awesome culture and just generally takes your breath away is an experience I am so thankful for. I’ve had the privilege to go on many family vacations to many cool place and the memories I’ve made on these vacations are some of my greatest childhood, teenage and young adult memories. A lot goes into family vacations, cooperation, good health, compromise and more. These vacations and memories have helped my family close. If you’d like to read more about vacation in Hawaii, you can click here! […]


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