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

Lanikai Pillbox Hike

The Pillbox Trail was closed for maintenance this summer and reopening on Aug 20th.  $250k was used to repair both of the military pillbox observation stations.  Happy hiking and enjoy the new renovations!

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 Beach and its surrounding residential neighborhood.

Lanikai Pillbox Views

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

Mokulua Islands

It's an incredible view the entire journey up that will mesmerize you!

The Hike up to the pillbox

Lanikai Pillbox View

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.  

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 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.

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 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.

Lanikai Pillbox Trail View

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!

Street View of Lanikai Pillbox Parking Area

Getting To Lanikai Pillbox Hike

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.

Lanikai Pillbox Trail Sign

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 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 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.

    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!

    Kailua Beach

    kailua Beach

    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.

    Town of Kailua

    Town of Kailua

    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!

    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 Barque 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 spot in the area, 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 overlook the North Shore coastline.   The views are breathtaking!

    Aloha & Enjoy!!

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