Kaiwa Ridge (Lanikai Pillbox) trail: the most beautiful view of the East Oahu beaches

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Written by SandrineUpdated on 05/03/22
1,5km round trip

The Kaiwa Ridge trail, more commonly known as the Lanikai Pillbox trail, is a fairly popular hike located in the eastern part of the island of Oahu. Its main interest is to offer superb views of the famous Lanikai Beach, often cited as one of the most beautiful beaches in the world!

We really enjoyed this trail which reveals the beauty of the Eastern Oahu landscape and being accessible to all. Despite its popularity, the views of the surrounding beaches and the ridges to the west make it one of our favorites on Oahu.

For the record, a Pillbox is actually a bunker, and you can find them all over Oahu's ridges. These were erected during the second world war to counter the Japanese ambitions. You can also visit them on the heights of Diamond Head.

Here are all our tips to prepare and enjoy the Kaiwa Ridge (Lanikai Pillbox) trail.

1The different itineraries of the Lanikai Pillbox trail

First, you will have to define the type of ride you want to do. You will have the choice between three options that you can easily see on the map at the bottom of the article.

The first is a round trip from the north from Kaelepulu Drive located just a short distance from Lanikai Beach and reach the Lanikai Pillbox, the main bunker. This is the busiest route. Count 1.5km round trip.

Expect not to be the only one who wants to enjoy the superb panorama!

The second option, still on a round trip basis, will allow you this time to reach the Lanikai Pillbox from Kamahele Street located west across the ridge. The advantage is to take a more intimate and almost deserted trail. It will be longer and will take you through dry brush and shrubs on the ridge overlooking the Mid-Pacific Country club golf course on one side, and the residential area of Wailea Point with the Pacific Ocean on the other. Count 2.3km round trip.

A final option will be to make a one-way trip from either Kaelepulu Drive or Kamahele Street, but this will necessitate having two vehicles or being picked up at the other end, as there is no fast road connecting the two points directly. Count 1.9km one way.

Hiking from Kaelepulu Drive in the north

The trail starts at street level and ends in a private cul-de-sac (but where you will not be able to park). The path leading to the first Pillbox is quite strenuous from the first few meters. The slope is indeed quite steep. So the advice is to warm up beforehand so as not to suffer too much in this part, which you can easily do between your parking point and the beginning of the ascent, as parking is not easy in this area.

Start of the potentially slippery Lanikai Pillbox.
View to the north and the beginning of the trail on the Kaelepulu Drive side.
Beginning of the Kaiwa Ridge / Lanikai Pillbox trail, view to the north
After 300m, view to the north and the beginning of the trail.

Once you reach the first pillbox, you'll have a few less strenuous metres left before you reach the Lanikai Pillbox. If you decide to simply make the round trip to admire the view, the climb ends here, in front of the superb view of Lanikai Beach, Moku Nui and Moku Iki, the two small islands in front of it, and if the weather permits you can even see Moloka'i and Maui on the right side of the view.

View of the eastern tip of Oahu, Molokai and Maui on the horizon.

You will then only have to turn around, being careful not to slip in the steepest parts.

Remember to look out for potentially slippery areas on the way to avoid the traps.

If you continue your progress on the ridge on a one-way trip, take advantage of the view from the Lanikai Pillbox and continue to the right. The progression does not present any particular difficulty except for the heat which can be stressful in this drier part of the ridge.

View of the Lanikai Pillbox from the Kaiwa Ridge that continues.

Once at GPS point 21.3812030, -157.7195629, (the only intersection you will come across), you will have to take the right path to join Kamahele Street. The path going to the left did not catch our attention because it is more hazardous and splits on many occasions, so many possibilities to make a mistake. The arrival is then at the end of the cul-de-sac where a car will be waiting for you (there is no public transport passing by here).

Hiking from Kamahele Street in the west

If you choose to hike the other way, the first challenge before starting the climb is to find a place to park! One solution is to be dropped off by a volunteer who can pick you up at the end of your hike.

The trail starts at the turnaround area at the end of Kamahele Street. You can't go wrong because the road is then in a private area, closed by a gate. There is a staircase on the right hand side, close to the wooded area, and this is where the ascent to the ridge leading to the Pillboxes begins.

The first part is relatively steep but much less grueling than the one on the Kaelepulu Drive side. Same remark that in the opposite direction, once you arrive at GPS point 21.3812030, -157.7195629, the path to take will be on the left. A succession of climbs and descents will make your progress more enjoyable as the landscape unfolds.

On Kaiwa Ridge looking towards the Ko'olau Range.

It won't be long before you reach the Lanikai Pillbox to enjoy the panorama. If you turn around, don't forget to turn right at the aforementioned intersection of paths.

If you continue towards Kaelepulu Drive, beware of the steep descent which can become acrobatic in recent rain or dry weather as the ground turns into unstable dust. The descent is often more dangerous than climbing on this type of pavement.

2Access to the Lanikai Pillbox trail

Access is easy as long as you don't park your car as close as possible to the two trailheads! It is indeed forbidden to park in Kaelepulu Drive, so you will have to find a parking space a little further away in the neighborhoods bordering Lanikai Beach. It is also difficult to park on Kamahele Street, as there are signs prohibiting parking in this residential area.

In both cases, you will have to expect a little walk to reach the beginning of the trail from your parking spot.

3Our feedback on the Lanikai Pillbox trail

We loved this hike, which can be described as a walk just a stone's throw from Lanikai Beach. It's a great viewpoint on this turquoise beach, but not only! The views of the surrounding landscape are superb. To the west, the ridge of the Ko'olau Range, which used to form the Ko'olau volcano, if it is clear, adds to the beauty of the panorama on the beach side. On the beach side, the view does not stop at Lanikai Beach. On a clear day you can see the island of Molokai and Maui to the east, Makapu'u Point and its lighthouse and the naval base on the Mokapu peninsula to the north, to mention only a few.

The view of Lanikai from the main Pillbox

We have judged this trail to be of medium difficulty, as it is short but with relatively steep gradients, whether you choose to start at its north or west end. In dry weather, the ascent is easy and accessible to the whole family, but in wet conditions, the trail can take on the appearance of a mud fighter despite the presence of ropes that can help you. In this case, the progression can become dangerous and unpleasant.

Clear weather will also be essential to enjoy the views and turquoise colours of the Pacific. And after the effort of discovering the Lanikai Pillbox Trail, what better way to dive in those crystal clear waters!

Our opinion
We like

Incredible views all along the trail

A popular but little frequented hike for Oahu

We don't like

Parking options

The slippery trail in wet conditions

About us

We are Sandrine and Flo, French thirty-somethings. In 2019 we quit everything to live our dream, become nomads and travel around the world. We left with our baby, Lena, who was only 5 months old at the time. After a first trip around the Pacific Ocean by plane and a long 3 months stay in Hawaii, we left to discover Iceland for 3 months on board our 4WD pickup truck and truck camper. Then we continued our adventure in North America.

Today, if we can continue this adventure, it is above all thanks to our blog, Smartrippers! We created it one day in 2016, with the desire to share our good travel tips, without thinking that it would lead us there! We have developed it a lot over the years and have become experts on our 3 favorite destinations: Hawaii, Iceland and the American West. We now guide you to these destinations to help you plan the trip of your dreams!

Follow our adventures!