Are you on searching for the best hikes in Oahu? It might seem incredibly difficult to drag yourself away from the island’s golden shores to explore one of the many hikes in Oahu however, this list is guaranteed to inspire you to reach for those hiking boots. Whether you are a beginner, an adrenaline junkie or simply have an hour to spare these are the best hikes in Oahu to admire the island’s natural beauty in its entirety.

Not only were we fortunate enough to complete these amazing hikes in Oahu, but we were fortunate enough to stay with a local family during our trip who gave us the insider tips we have shared with you. This was due to the fantastic cultural exchange platform, Workaway. There are hosts in over 170 countries who allow you to stay for free in exchange for sharing your culture and a few hours volunteering a day. If these best hikes in Oahu have inspired you to visit this beautiful island then staying with a local family is one of the best ways to truly embrace the Aloha way of life and the vibrant culture this country has to offer. For more information on finding your dream host and Workaway experience (like ours in Oahu) read this post.

This is a fabulous guest post by Darren and Lauren from Far Am A Gan

5 Best Hikes In Oahu For All Skill Levels

#1. Diamond Head – One of The best hikes in Oahu for views of Honolulu

Difficulty: Medium

Best time to hike Diamond Head: Anytime – The trail is open 6am until 6pm, although last entry is 4.30pm.

How long does it take to hike Diamond Head? 1.5-2 hours.

Arguably, one of the best things to do in Oahu, this hike shouldn’t be missed! Not only can you see Diamond Head from Waikiki beach but you can walk from there too. Be warned, however, as it is within walking distance of Waikiki it is one of the most touristy best hikes in Oahu. Once you see the views from the top you cannot blame everyone for wanting to hike it.

The landmark earned its name from British sailors in the 1800s who nicknamed it Diamond Head from the glittering stones that sparkled at the top of the crater.

Although only a 1.4 mile trip, it is deceptively difficult due to the steep gradient and typically takes 1.5-2 hours. If you are spending a shorter amount of time like 4 days in Oahu, make sure to budget time for this hike!

Most of the trek has handrails and paved steps due to the US Army building the trail in 1908 as part of the military coastal defense system. As you reach nearer the top of Diamond head, more of this military influence will become obvious as you climb through a bunker and an amazing spiral staircase through the old Fire House.

Considered one of the best hikes in Oahu because if you brave the scarily narrow corridors and steep steps you will be rewarded with the most stunning views of Honolulu. Don’t forget the enormous volcanic crater created over 300,000 years ago – as you look down on it, you really will feel on top of the world!

Top tips for hiking Diamond Head

• Be warned, if you are at all claustrophobic there are several narrow stairways and dark corridors near the summit which I struggled with, however they were worth it for the views from one of the best hikes in Oahu!
• Oddly, when we hiked it there was a man selling “certificates” at the top. Beware of this tourist scam!
• Make sure to take cash as there is a small entry fee of $1 per person for pedestrians or you pay $5 for a car and they do not accept card.

#2 The Makapuu Lighthouse – One of the best Easy hike in Oahu for families

Difficulty: Easy

Best time to hike The Makapuu Lighthouse: Sunrise – for the views & because parking gets crazy busy later in the day

How long does it take to hike to Makapuu Lighthouse? Approx 1.5 hours – expect longer as there are many lookout spots and photo opportunities.

Makapuu Lighthouse trail is located in the South East part of Oahu, beginning at Makapuu Head and along the western ridge, passing the historic Makapuu Lighthouse. Built in the early 1900s, you may recognize the iconic lighthouse from the movie, “50 First Dates” where Adam Sandler and Drew Barrymore shared their first kiss.

If you are looking for easy hikes in Oahu, the Makapuu Lighthouse is perfect for beginners and families as it is a two-mile hike, entirely paved with only a slight incline. Although quite busy due to the accessibility, the hike never feels crowded due to the numerous lookout spots and particularly wide paths.

During this easy hike in Oahu, expect to see the local landmark Rabbit Island and on a clear day the neighboring Molokai and Lanai islands. If you have time, take an hour detour to Makapu’u Tidepools. Beware of rough seas causing scarily high waves, however, if on a calm day it is worth the detour. You can admire the sea as it blasts through the cave creating an impressive blowhole!

Top tips for hiking The Makapuu Lighthouse

• Arrive early, as there is only a small car park which fills up so fast and many cars have to park along the road to complete one of the best hikes in Oahu!
• Although one of the best hikes in Oahu for children note there is no shade from the hot Hawaiian sun and no restrooms so be prepared for this!
• If you hike during migration season (November until May) you are likely to spot humpback whales during your hike!

#3 Lanikai Pillbox Hike/Kaiwa Ridge Trail – One of the best hikes in Oahu if you’re short on time

Difficulty: Easy/Medium

Best time to hike the Lanikai Pillboxes: Anytime – although we did it around 1pm and it was crazy hot!

How long does it take to hike The Kaiwa Ridge Trail? 30 minutes to the first pillbox, around 90 minutes to hike all 3.

Heading to the East side of the island, the Lanikai Pillbox hike (also known as the Kaiwa Ridge Trail) offers breathtaking views and is one of the best hikes in Oahu if you’re short on time! Grab that sought-after shot from the roof of a Lanikai pillbox as you overlook many famous Oahu landmarks such Lanikai Beach, Mokula Islands, Kailua Beach, Kaneohe Bay and The Chinaman’s Hat.

Easy hikes in Oahu are hard to find, so when this hike began in a residential street I was instantly fooled into thinking it was going to be a relaxing occasion, (I even wore a dress in the belief it would be a leisurely stroll!) However 5/10 minutes in I was faced with such a steep incline I had to use my hands to climb and there was even a rope to pull yourself up. Depending on weather, this may have you off to a very slippery start to this best hike in Oahu! Thankfully, after that, there is only one more difficult incline around 30 minutes in, just before the first Pillbox so despite those two tricky moments this hike is suitable for beginners.

On your way back down, expect amazing views of the enchanted lake and Kaneohe Marine base. This is definitely one of the best hikes in Oahu to grab postcard-perfect views of Oahu without (barely) breaking a sweat!

Top Tips for hiking The Lanikai Pillboxes

• Park in the legitimate spaces! There has been rumor this hike may be made illegal, as it starts in a residential street many careless people have been parking illegally. Please avoid this and only park in permitted spaces otherwise this incredible hike will be no longer.
• We are all in favour of a good Instagram pic and this is one of the best hikes in Oahu for getting some great photos! That being said, be warned, you will have to climb onto the roof of the pillboxes so take extra caution. No Instagram pic is worth risking your life for.

#4. Koko Head – One of the best hikes in Oahu if you like a challenge

Difficulty: Hard

Best time to hike Koko Head: Sunrise

How long does it take? We are not particularly fit and it took us an hour to the summit

This is of the best hikes in Oahu due to the insanely rewarding views from the top, however, in order to reach the summit of Koko Head you will need to endure 1,050 steps first. The “steps” were once a railroad, which ran supplies and military personnel to the Air Force Station at the top of Puu Mai in World War II.

Due to the strenuous climb (guaranteed to make you drip with sweat) it is recommended to begin this best hike in Oahu around 5.30 am when it is still dark and consequently much cooler. This means you will be rewarded with the most spectacular sunrise at the summit. It is incredibly popular with fitness fanatic locals who challenge each other to RUN up it. We were shocked with the numerous athletes carrying backpacks as they jogged up the 1,050 steps – my red faced, sweaty self much, much further behind.

The struggle to the top is most definitely worth it and immediately each of those strenuous steps become a distant memory once you summit one of the best hikes in Oahu. After admiring the incredible views of the surrounding shore – including Hanauma Bay, Sandy Beach and Koko Marina – it is time for the climb down. In my opinion, this was harder than the hike up. Partly because my legs were practically numb and partly because some of the steps are particularly wide apart and quite high. This resulted in a few heart-pounding moments where I feared I would fall between the gaps in the steps to the overgrown below. In the end, this is one of the best hikes in Oahu and certainly deserves it’s title as one of the toughest in Oahu and definitely not for the faint hearted!

Top Tips for hiking Koko Head

• As it is best to start the hike around 5/5:30 am make sure to take a flashlight, or if using your phone light make sure to have plenty battery to photograph the stunning sunrise at the top. You are going to want to capture the memories from completing one of the best hikes in Oahu.
• This is probably obvious, but please eat before you hike! As it was so early, I avoided breakfast but nearly fainted during the hike as the temperature (and step count) gradually increased. You won’t be able to enjoy one of the best hikes in Oahu if you are faint with hunger!

#5. Stairway to Heaven – One of the best hikes in Oahu if you’re feeling rebellious

Difficulty: Hard

Best time to hike the Stairway to Heaven: Never

How long does it take to hike the Stairway to Heaven? 4-6 hours

Chances are if there’s any hikes in Oahu on this list that you’ve heard of, it’s The Stairway to Heaven. I could bet money, you’ve not only heard of it but you’ve likely been mesmerized by the Instagram pictures and insane Youtube footage. Personally, I have not completed this hike myself and for the simple reason (that many people do not realise, due to said Instagram pics) is that it is illegal. I feel it still worth mentioning, due to it’s fame and to properly warn anyone considering hiking this infamous trail in Oahu. Although it is one of the best hikes in Oahu for many reasons, it is against the law to hike so understand the risk if you choose to do so.

The original name Haiku Stair is nicknamed the Stairway to Heaven due to the 4000 steps taking you to the clouds above Oahu. Not only is there numerous “No Trespassing” signs there are guards 24 hours a day. If the $1,000 fine won’t deter you, the storm damaged stairs down vertical ridges might.

There is a longer and legal route to reach the Stairway To Heaven which is about 6 miles long, but you aren’t able to actually hike the Haiku Stairs. Perhaps you can stand on a few for some photos, but you won’t be able to hike the whole ridge without risking fines.

If you fancy a little vacay in jail, then by all means take the risk – arguably, the view must be worth it if so many people break the law to reach the summit. However, is a few Facebook likes really worth it? Sure, it is one of the best hikes in Oahu if you want to risk fines, jail time, and maybe get a pretty epic photo for Instagram. We are really quite surprised how many articles list Stairway To Heaven as one of the best hikes in Oahu without telling readers that it is illegal! Please make an informed choice if you decide to go this route on your trip!

There are so many fantastic views, it is hard to narrow down to the top five best hikes in Oahu! From easy hikes in Oahu to more difficult and even illegal jaunts, there is something for everyone! Let us know in the comments if you have ever went hiking in Oahu and what hike you would add to this list! If you are looking for somewhere to stay in Oahu there are plenty of options ranging from family-friendly to luxury resorts. While you in Hawaii, you may also want to check out The Best Hikes On Maui too! 

Author Bio: After 6 years of long distance, Darren and Lauren quit their day jobs to live the day dream. Now they catch flights with each other instead of to see each other, documenting their tales and fails through their blog Far Am A Gan. Far am a gan translates to “where am I going” from the Scot’s language, Doric. Likely muttered several times a day by this travelling twosome as their cheeky Scottish charm gets them into all sorts of epic adventures around the globe.

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