Hiking the Lanikai Pillbox Trail (Kaʻiwa Ridge) on Oʻahu, Hawaiʻi
Distance (Roundtrip): 0.9 miles / 1.4 km
The Lanikai Pillbox Trail on the east side of Oʻahu is a local and visitor favorite, as the short hike, which climbs to two WWII-era pillboxes at the top, is without a doubt one of the best sunrise hikes on Oʻahu and one of the best day hikes on the island because of the stunning turquoise-blue water that can be seen just offshore on a clear day!
This is all to say that the effort-to-reward to reach the top of the Lanikai Pillbox Trail speaks for itself, given how short the hike is—only 0.45 miles (0.7 km) each way—making the trail one of the best things to do on Oʻahu, especially early and late in the day!
Now, I can’t talk about the Lanikai Pillbox Trail without addressing the challenges of simply accessing the trail. By this, I mean that it’s a shame what the residents of Lanikai have done to make parking within the neighborhood nearly impossible for both the trail and Lanikai Beach. For this reason, I highly recommend reading through the following section if you plan on driving to the Lanikai Pillbox hike.
Lanikai Pillbox Trailhead Parking
The Lanikai Pillbox Trail is the single most difficult hike to find parking for on Oʻahu.
As of July 2025, the City and County of Honolulu is nearing the final stages of a plan that will ban all parking on both ʻAʻalapapa and Mokulua Drive from 10 a.m. to 4 p.m.—the main one-way loop that circles Lanikai.
This means that during these hours, parking for both the Lanikai Pillbox Trail and Lanikai Beach will only be allowed on the cross streets.
I anticipate these changes will take place in the coming months following this announcement, and while I do my best to keep this information up to date, please read the signs carefully whenever and wherever you decide to park in Lanikai.
What Do I Recommend?
Currently, even before these new rules take effect, my first sentiment is still true: the neighborhood is an incredibly difficult place to find a legal place to park, and this will only get more challenging when these changes are implemented.
That said, read the signs carefully if you plan to park anywhere in Lanikai.
I stress this because there are countless niche parking laws that have to do with how far away you can park from bike lanes, driveways, intersections, fire hydrants, and sidewalks, and 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.
While I can’t help much with the unimproved sidewalk rules, know that tickets are handed out daily to anyone breaking any one of the following parking laws:
Driveways – No parking within 4 ft. (1.2 m)
Intersections – No parking within 20 ft. (6.1 m)
Fire Hydrants – No parking within 10 ft. (3 m)
Sidewalks, Crosswalks, & Bike Lanes – No parking or blocking in any way
There is honestly not another trail on Oʻahu that I would go into this much detail over, but in Lanikai, it really does matter!
For all these reasons, I personally recommend either arriving early to hike the trail for sunrise or parking outside of the Lanikai neighborhood—perhaps at Kailua Beach Park—to walk in, take the bus, or take an Uber to the trailhead.
I say this because, while you can try to arrive midday for the hike, parking will likely be very hard to come by, as the limited availability within Lanikai serves both the hike and the beach—not to mention the residents.
Google Maps Directions: Lanikai Pillbox Trailhead
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.
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 all uphill, ascending just over 400 ft. (122 m) from the trailhead to the second pillbox—the highest and last pillbox on the hike.
As I’m sure is obvious, there is very little shade on Kaʻiwa Ridge, which is why I highly recommend hiking with a hooded sun shirt to stay safe, as one can be useful here and on countless other adventures across Hawaiʻi.
Some hikers may prefer to carry trekking poles for the steep and slippery hike back down—and yes, I do want to stress slippery, as the dry, loose soil has, unfortunately, been the culprit in fatal accidents on the Lanikai Pillbox Trail.
Lower Lanikai Pillbox
After just 0.3 miles (0.5 km), the Lanikai Pillbox Trail reaches the first and lower of the two WWII-era pillboxes, with the second located roughly 0.1-mile (0.2 km) up the ridge from this point.
This is the short 0.1-mile (0.2 km) trail between the Lower and Upper Lanikai Pillbox.
Upper 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 just offshore, I recommend reading the next section below, as 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!
Kayaking to the Mokulua Islands
The two islands seen just offshore from the Lanikai Pillboxes are accessible to the public by kayak only.
That said, kayaks can be easily reserved using the links below, which make for great options 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.
Lanikai Pillbox Trail (Back Way)
[Not a Recommended Route for Visitors]
There is more than one route to reach the famous Lanikai Pillboxes. However, 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.
However, restoration work is underway, but this is unfortunate for those who are interested in the subject because I can almost always find a number of native plants on any hike, even in the most invaded areas.
Now, what you will see on Kaʻiwa Ridge is invasive grasses, Koa Haole trees, and a few non-native sporadic Gaïacwood trees. For this reason, 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.
If you would like to learn more about these and many other native Hawaiian plants from across the islands, I encourage you to check out my separate post linked below.
Read My Separate Post: Native Hawaiian Plant Guide
