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Lanikai Pillbox Hike

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, rewarding hikers with some of the best vistas of Oahu’s windward side.

Lanikai Pillbox Hike

Disclaimer – all Oahu hikes have different challenges and hazards that can be dangerous and may inflict injury. Know your fitness and skill level before embarking in any hike.  Stay on trails and obey posted signs. The information on this site is for your reading pleasure only.  Please hike at your own risk.

Lanikai Pillbox Hike is ranked intermediate because of the steady steep grade of the uphill climb right from the start of the trail head.

Throughout the climb, hikers are rewarded with views of the Mokulua Islands, Kailua Beach, Lanikai Beachand its surrounding residential neighborhoods.

Lanikai Pillbox Views

In the distance, you can also see Kaneohe Bay, Chinaman’s Hat, Waimanalo Bay, and the Makapu’u Lighthouse.

Bundle your Oahu attractions: visit Pearl Harbor, see the Bishop Museum & Iolani Palace, sign up for a Hawaiian Luau, and engage in other fun adventures around the island, consider getting an Go Oahu Card.

Oahu Go Card

We are big fans of the Go Oahu Card, because you are able to plan out all your activities, bundle them together, and receive deeper discounts across the board.

Mokulua Islands

Hikers are rewarded with mesmerizing views the entire way up to the pillboxes.


The Hike to the Pillboxes


Lanikai Pillbox View

The Lanikai Pillbox Hike is a moderate 1 hour to 90 minute hike (roundtrip), depending how far you decide to go.  You can easily reach the first old military pillbox bunker in about 20 to 30 minutes.  

Lanikai Pillbox Trail

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. 

Lanikai Pillbox Trail View

You also have the option of trekking another 30 minutes farther along the Kaiwa Ridge Trail and it will take you around the coast a bit farther, and finally lead you down to the residential houses located on A’alapapa Street.  From there you will need to walk approximately half a mile back to Ka’elepupu Drive, where you first started.


Lanikai Pillbox
Lanikai Pillbox Trail


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 that you could 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.

Lanikai Pillbox Trail View

The initial 10-yard (approx) vertical climb through thick brush might seem a little intimidating at first, but the steep part is short and you will be fine once you get started and the trail opens up to the fabulous ocean views to the left.

Although this Oahu hiking trail is rated moderate because of its initial steep climb, you often find kids and families along the ridge top, enjoying the adventure and views!


Street View of Lanikai Pillbox Parking Area



Getting To Lanikai Pillbox Hike


Your best option is to drive to Lanikai for this hike.  It will take you about 40 minutes by car from Waikiki, or 1 hour plus by bus.

Lanikai Pillbox Trail Sign


The starting point of the Lanikai Pillbox Hike is located on a small no name street that branches 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 Hike.

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.

By Car

Mid-Pacific Country Club
  • Jump onto the H-1 Freeway from Waikiki and head west.
  • Merge onto the Pali Hwy (Hwy 61) and follow it to the eastern side of the island
  • Turn right on Kailua St (in the town of Kailua)
  • Make a right turn onto Kawailao St and follow it until it becomes Aalapapa St.
  • Make a right turn onto Ka’elepupu Dr


  • 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.

    By Bus

    • 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 Drive will be the 2nd street once you enter the Lanikai residential area.  
    • Let your bus driver know that you would like to be dropped off at the A’alapapa Drive stop.  Ka’elepupu Drive is one block up the street, where you will need to walk up to the hiking entrance.

    Oahu map of the Lanikai area



    Hiking Tips

    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 including the following:


    • Water
    • Hat
    • Shoes with a grip
    • Sunscreen
    • Light snacks
    • Camera
    • Backpack

    In the Lanikai Pillbox Hike Area


    Windward Oahu Beaches!

    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

    Lanikai Beach

    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!


    Kayak to Mokalua Islands

    Kailua Beach Kayak Tour


    Experience the beauty of the Mokalua Islands, and the Windward Coastline from a distance, on a fun guided kayak ride!  It’s amazing enough to just step onto Kailua beach, but paddling out gives you a whole new perspective. Not to mention observing the crystal clear waters below as you journey out.

    This is a special 2 hour adventure that you must plan a head and sign up before arriving at the beach.  It includes transportation, lunch, snorkel gear, life jacket, dry bag, and caters to beginners to more advanced kayakers. 

    Book a Kayak Ride Now


    Kailua Beach

    kailua Beach

    Kailua Beach Park offers more pristine beaches, aqua blue waters, and the definition of the word paradise!  It also has park facilities available if you need them.


    Town of Kailua

    Town of Kailua

    On your way to Lanikai, you will pass through the charming downtown area of Kailua.  There are many fun shops and restaurants you can duck into.  Take a stroll if your legs are still up for it!


    Kailua Restaurants

    Kailua Restaurants


    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.


    Lanikai Juice

    Lanikai Juice


    Also consider hydrating yourself after the hike at Lanikai Juice,  It’s a great local spot serving tasty, healthy smoothies, and treats!


    Sister Hike in the North Shore

    Ehukai Pillbox Hike


    Looking for another hike simular to Lanikai?  Head to the North Shore and turn your attention to a ridge above the Banzai Pipeline.  The Ehukai Pillbox Hike is another great Oahu hike that is a 30 minute climb up to two old military bunkers overlooking the North Shore coastline.   The views are breathtaking!



    Aloha & Enjoy!!



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