Hiking the Lanikai Pillbox Trail (Kaʻiwa Ridge) on Oʻahu, Hawaiʻi
Distance (Roundtrip): 0.9 miles / 1.4 km
The Lanikai Pillbox Trail is easily one of the best sunrise hikes on Oʻahu!
I say this because the effort-to-reward is one of the best in terms of how short the hike is, at only 0.45 miles (0.7 km) each way, making the Lanikai Pillboxes one of the easiest and most beautiful sunrise hikes on the island!
That being said, it’s ashamed what the Lanikai neighborhood has done to make parking within Lanikai nearly impossible, which is why I highly encourage you to read through the following section if you plan on driving.
Lanikai Pillbox Trailhead Parking
If you are going to try and park within Lanikai, I highly recommend that you read the signs carefully when trying to find a spot anywhere in the Lanikai neighborhood.
I stress this because there are countless little niche parking laws that have to do with how far away you can park from bike lanes, driveways, intersections, fire hydrants, etc., and on top all of this, there are special parking laws about what days of the week are okay to park in Lanikai.
To make matters worse, the City and County of Honolulu considers many unmarked places along the streets in Lanikai to be 'unimproved sidewalks,' meaning what may look like a perfectly fine spot to park off the street is actually a 'sidewalk,' making it illegal to park.
Furthermore, tickets are typically handed out daily to anyone breaking one of the above parking laws.
For all these reasons, I recommend parking outside of the Lanikai neighborhood, perhaps Kailua Beach Park, to walk or take the bus to the trailhead.
Lanikai Park
The photos below show some of the few possible areas to park in Lanikai near Lanikai Park.
However, even these spots can be extremely hard to come by, and if they are available, you still may be risking a ticket if it’s one of the days of the week that street parking is banned within the neighborhood.
Google Maps Directions: Lanikai Park
Hiking the Lanikai Pillbox Trail
Since there is no parking near the Lanikai Pillbox Trailhead, be prepared to walk some distance unless you have the luxury of getting dropped off.
In any case, the Lanikai Pillbox Trail begins between a couple private residences on Kaʻelepulu Drive, as shown below.
For nearly the entire length of the hike, the Lanikai Pillbox Trail is an uphill hike, ascending just over 400 ft. (122 m) from the trailhead to the second pillbox—the highest and last pillbox on the hike.
As you can see from these photos, there is very little shade on the 0.5-mile (0.8 km) Kaʻiwa Ridge, which is why I don’t recommend the Lanikai Pillbox hike during the heat of the day.
First Lanikai Pillbox
After the first pillbox, the second is only a short 0.1-mile (0.2 km) walk away, with hardly any more elevation to gain.
Second Lanikai Pillbox
The second Lanikai Pillbox is typically the end of the hike for most people on Kaʻiwa Ridge.
However, if you are interested in visiting the two famous islands that you can see offshore, read the next section below.
Kayaking to the Mokulua Islands
The two islands that you can see offshore from the Lanikai Pillboxes are accessible to the public by kayak only.
Furthermore, kayaks can be easily reserved using the links below, and these are great options to choose if you are visiting Oʻahu, so that you don’t have to worry about transporting a kayak to and from the beach.
Additionally, one of my favorite things about booking through Viator is the reserve-now-and-pay-later option. As long as you’re booking more than three days in advance, you have the option to book ahead and cancel in the future if you change your mind.
All said, planning both the Lanikai Pillbox Trail and a kayak tour to the Mokulua Islands is a great way to spend a full day on Oʻahu’s east side!
Lanikai Pillbox Trail (Back Way)
[Not a Recommended Route for Visitors]
There is more than one route to reach the famous Lanikai Pillboxes, but if you’re visiting Oʻahu, I don’t recommend any of the alternate routes up Kaʻiwa Ridge.
The back way up Kaʻiwa Ridge is a bit longer and more confusing, which is why I believe they are best for residents only.
Read My Separate Post: Lanikai Pillbox Trail (Back Way)
Native Plants on the Lanikai Pillbox Trail
Outside of ʻUhaloa, there are nearly no native plants on the Lanikai Pillbox Trail.
Generally speaking, I can always find a number of native plants on any hike, even in the most invasive areas, but the Lanikai Pillbox Trail is the exception.
This is because Kaʻiwa Ridge is dominated by invasive grasses, Koa haole trees, and a few non-native sporadic Gaïacwood trees that cover the ridge. Therefore, you have a much better opportunity to see native Hawaiian plants down at Lanikai Beach than on the hike.
Some of these include Naupaka, Pōhuehue, and if you’re lucky, Maiapilo.
All said, if you’re interested in learning more about these and other native Hawaiian plants from across the islands, I encourage you to read more in my separate post.
Read My Separate Post: Native Hawaiian Plant Guide
