The Lanikai Pillbox Hike, also popularly known as the Kaiwa Ridge Trail, is one of the most picturesque and pleasant Oahu hiking trails. This intermediate hike rises just above beautiful Lanikai Beach Oahu, rewarding hikers with some of the best vistas of Oahu’s windward side.
Lanikai Pillbox Hike is ranked intermediate because of the steady steep grade of the uphill climb right from the start of the trail head.
The Lanikai Pillbox Hike is a moderate
1 hour to 90 minute
round trip, depending how far you decide to go.
You can easily reach the first old military pillbox bunker in about 20
to 30 minutes.
From here, another 10 minute walk along the top ridge will take you to the second pillbox. Most hikers turn around at this point, and travel back down the Kaiwa Ridge Trail from where they originally started.
You also have the option of trekking another 30 minutes further along the Kaiwa Ridge Trail that will take you around the coast a bit farther, and finally lead you back down to the residential houses located on A’alapapa Street. From here you will need to walk back approximately half a mile to Ka’elepupu Drive, where you first started.
You will want to wear appropriate hiking shoes and take caution climbing up and back down the Lanikai Pillbox Hike. It’s a long steep climb up the initial part of the ridge, with lots of loose rocks and gravel to slip on.
There used to be a climbing rope on the side of the trail to help you along your way. But since the rope is gone now, I like to walk through the tall grass on the side of the hill, which seems to give me a little more grip.
The initial 10-yard (approx) vertical climb through thick brush might seem a little intimidating at first, but you will be fine once you get started and the trail opens up to the fabulous ocean views to the left.
Although these Oahu hiking trails are rated moderate because of its initial steep climb, you often find kids and families along the ridge top, enjoying the adventure and views!
Your best option is to drive to Lanikai for this Oahu hike. It will take you about 40 minutes by car from Waikiki, or 1 hour plus by bus.
The starting point of the Lanikai Pillbox Hike is located on a
small no name street branched off
of Ka’elepupu Drive -trust me…its easy to find!
You will see it directly across
from the Mid-Pacific Country Club. There should
also be a small sign further up this “street” indicating the Pillbox
Next to the sign, you will need to step through some brush and immediately climb up about 10 feet to reach the Kaiwa Ridge Trail.
There are about 7 parking spots located on the right hand side by the entrance gate to the Mid-Pacific Country Club. Park and walk up the side street on the left hand side and look for the small “Pillbox Hike” sign.
From Kuhio St in Waikiki, take the number 20 Oahu bus to the Aloha Tower headed towards Kailua. Once in downtown Kailua area, transfer to the number 70 shuttle bus. Ka’elepupu Dr will be the 2nd street once you enter the Lanikai residences. Let your bus driver know that you would like to be dropped off at the A’alapapa Dr stop. Ka’elepupu Dr is one block up the street, where you will need to walk up to the hiking entrance.
Closest public restroom is located at Kailua Beach Park if you need to use one.
Come prepared to all Oahu hikes with the proper gear and aid:
The 2 most beautiful beaches on Oahu just happen to lie below the Kaiwa Hills. It would be a shame to not spend a little R&R time on at least one of them!
Lanikai Beach backs up to the luckiest residents on the island! This Oahu beach has pristine powder sand and tranquil aqua blue waters. I could easily camp out on this beach all year long and call it home!
Kailua Beach Park offers more pristine beach real estate, magic waters, and the definition of the word paradise! It also has park facilities available if you need them.
On your way to Lanikai, you will pass through the charming downtown area of Kailua. There are some fun shops and restaurants in the area. Take a stroll if your legs are still up for it!
Among the slew of Oahu restaurants in Kailua, I would recommend heading over to Boots & Kimo’s for good breakfast eats, and L&L Barbeque or Zippy’s for an inexpensive, fast, and satisfying plate lunch.
Also consider rehydrating yourself after the hike at Lanikai Juice –it’s a great spot in the area, serving tasty healthy smoothies and treats!