Hiking in Hawaii, especially Oahu, is an incredibly rewarding experience.  With the vast amount of beaches and mountains, hiking in Oahu offers an unlimited amount of trails and epic view points.  While we are always up for a challenge, we wanted to make the most of our beach time, and sought out some of the easy hikes on Oahu.

While hikes around Oahu can vary in difficulty and distance, we decided to conquer some of the hikes considered to be easy.  And let me tell you, just because these hikes are considered to be on the easy side for Oahu, doesn’t dismiss the incredible views once you reach the top.

A word of caution before your Hike

Keep in mind, that all of these hikes are up hill and will require some physical stamina.  If you are in moderate shape, you should be able to manage these hikes with little difficultly.  It is important to note, that you should be the judge of your own health and physical abilities while hiking.  Hiking and trail conditions come with risks, use caution as you proceed. 

Be mindful that many of these trails are without shade.  With that being said, I highly recommend that you start your hikes early in the morning.  This will help you avoid the strong UV rays and heat.  Plus, then you can spend the rest of the day at the beach!  It is also important that you bring plenty of water and wear study shoes while hiking.  Trails vary greatly in their level of difficulty.  The following are considered to be some of the easy or moderate hikes you can do on Oahu.

What is a Pillbox?

Historically, Oahu’s military, strategically placed a number of “Pillboxes” (military protection points) mountain side, close to the coast, to watch for potential threats.  Nowadays, these pillboxes remain empty and are the source of many incredible lookout points around Oahu.  The pillboxes on these hikes are open to explore, allowing you a glimpse of the past.

Diamond Head Hike

Diamond Head is located right in the heart of Waikiki and is the most popular easy hike on Oahu.  Being so close to the tourist sector, Diamond Head gets very busy, even early in the morning. 

The trail at Diamond Head starts off gradually and eventually leads you to a number of uphill switchbacks around the crater.  This hike can take anywhere from 30 minutes to an hour depending on your speed and how many people are in front of you.  The trail is narrow, so at times, you might be stuck going at the pace of the people in front of you.

Once you complete hiking through the crater, you will be brought to some narrow tunnels and staircases that lead you to the main lookout point.  The main lookout point at Diamond Head gives you panoramic views of Waikiki and the surrounding coastlines. 

If you’re visiting Diamond Head on your own, you have two options to enter, you can drive in and park for $5 USD (if there is space) or walk in for $1 USD.

Ehukai Bunker (Peace Sign) Pillbox

The Peace Sign Pillbox is located right next to a school on the North Shore.  This hike is relatively quick and takes about 30 minutes to reach the top.  Unlike the other hikes, this trail is pretty quiet, at least when we were there.  The trail starts off flat and then takes you up hill.  Although this hike is pretty quick, there is a pretty good incline in spots.

Along the way, you will come across some rest points.  Take these opportunities to peek at the view as you make your way uphill.  At the top, you will be greeted by some nice views of the ocean.

Depending on when you do this hike, it may be possible to find a parking spot on site.  We did this hike on the weekend and there were plenty of parking spaces.  If you do this hike during the week, when school is in, it might be a bit tricker.

Lanikai Pillbox Hike 

The Lanikai Pillbox hike is the most difficult of these four hikes.  This hike begins with a steep grade right from the beginning and has some ropes in place to assist you.  Once you pass the initial incline (about the first 5 minutes), the hike becomes a more gradual uphill climb.

Once you reach the top, you will be met by the Lanikai Pillbox and amazing views of the area.  The ridge line continues for quite a distance and you can continue on this path if you wish to.  If you have time, I suggest that you pair this hike with Lanikai Beach as it is absolutely stunning.

The Lanikai Pillbox is about 40 minutes from Waikiki, depending on traffic.  There isn’t a specific parking lot that caters to this hike, so you will have to look around for a parking spot.  If you go early in the morning, you will likely be able to find a spot relatively close to the trailhead.  Be cautious of where you park as there are a number of homes in the area.

Pink (Maili) Pillbox Hike 

The Pink Pillbox Hike is my favourite of all the easy hikes on Oahu.  This hike isn’t super difficult, but it is hot!  There is little to no shade on this trail, making it difficult if you’re not used to being exposed to the sun and heat.  It is best to do this hike as early as possible. This hike zigzags up the side of the mountain and will likely take you under an hour to reach the top.

This hike has been made popular by the bright pink pillbox that has been coloured in honour of breast cancer awareness.  Not only does this hike hold sentimental value to a lot of hikers, it also has EPIC views.  With two stunning beaches on either side of the pillboxes, and an incredible ridge line in the background, it’s really difficult to leave this amazing view.

The pink pillbox has become so iconic that people often don’t realize there are also 3 other pillboxes on this hike as well.  With a total of 4 pillboxes, there are an abundance of opportunities to take in the great views at the top of the ridge line.

This hike is found in the suburbs on the west coast of Oahu.  When we were there, there was plenty of street parking at the beginning of the trail.

Where to find these hikes on Oahu

These four hikes are nicely spread out across Oahu’s coasts.  This gives you a great opportunity to explore different areas of the island.  These hikes are all pretty well known and easy to find.  We simply plugged the name of the hikes into google and followed the directions.  If you’re having difficulty locating these hikes, the above map shows you a pin of where each is located.

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