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
Lanikai Beach, rewarding
hikers with some of
the best vistas of
Oahu’s windward side.
Hike is ranked
intermediate because of the steady
of the uphill climb right from the start of the trail head.
Hikers are rewarded with mesmerizing views the entire way up to the pillboxes.
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.
From here, another 10 minute walk along the 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 hour 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 mile back 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 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
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!
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.
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
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.
and walk up the side street on the left hand side and look for the
small “Pillbox Hike” sign.
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:
The 2 most
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!
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!
Experience the beauty of the Mokulua 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.
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.
On your way to Lanikai, you will pass through the charming
downtown area of Kailua Town. There are many fun shops and
restaurants you can duck into. 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 Barbecue or Zippy’s
for an inexpensive, fast, and
satisfying plate lunch.
Also consider hydrating yourself after
the hike at Lanikai Juice, It’s a great local spot serving
tasty, healthy smoothies, and treats!
Looking for another hike similar 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