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
If you are going to park within Lanikai, I highly recommend reading 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, and sidewalks. On top all of this, there are special parking laws about what days of the week parking is allowed 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, which is why I personally recommend parking outside of the Lanikai neighborhood, perhaps at Kailua Beach Park, to walk in or take the bus to the trailhead.
Lanikai Park
The photos below show some of the very limited areas where hikers and beachgoers can 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
My Hawaiʻi Hiking Checklist
Osprey 3L Water Bladder - The Osprey 3L water bladder is the most universal hiking and backpacking water bladder on the market, and it’s my go-to because of the slide-off seal that allows it to be quickly filled from the top. Additionally, individual parts are easily replaceable, such as the bite valve.
Blister / Heel Protectors - I swear by these cheap, amazing heel protectors to prevent blisters for nearly every kind of hiking and backpacking that I do!
Black Diamond Headlamp - Personally, I recommend the Black Diamond Storm because it is one of the brightest, lightest, and longest-lasting headlamps on the market—and trust me, the weight-to-battery-life ratio really does matter!
Hiking / Trail Running Shoes - Depending on the type of trail, I prefer to use either the Keen Targhee for longer, more rugged hiking or the HOKA Zinal Trail-Running Shoe for lighter, less intense trails. In either case, both have been amazing to me for many years across countless environments, and both can be found in men’s and women’s sizes. - (Men’s Keen / Women’s Keen) (Men’s HOKA / Women’s HOKA)
Waterproof Rain Shell - You never know when it may rain, and I’ve learned over the years that a rain shell is far better than a rain jacket. By this, I mean that it’s best to have something that the water will roll right off of, which is why I recommend the Patagonia Torrentshell 3L available in both men’s and women’s sizes.
High SPF Sunscreen - Packing high-SPF sunscreen is a must for long days outside!
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 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
More Oʻahu Adventures
If you’re interested in reading about some more amazing Oʻahu adventures, check out my separate posts below!
Best Hotels & Restaurants in Waikīkī
If you’re trying to decided where to stay on Oʻahu, check out my top 10 list for the best resorts and restaurants in Waikīkī.
I break down what makes one hotel a better choice over another, so that you can find the best fit for your stay on the island.
Read My Separate Post: Best Waikīkī Hotels & Restaurants
Waikīkī
HNL Airport-Hotel Shuttle
Prices on ride-share apps like Uber/ Lyft cannot beat the price of booking your hotel shuttle prior to arrival. I say this because there are additional fees for ride-share airport pick-ups at Honolulu Airport (HNL), which is why I recommend booking your transportation in advance using the options below.
Additionally, the last option below will go as far as the Ko ʻOlina Resorts on the West Side and Turtle Bay on Oʻahu’s North Shore!
Best Way to Book Rental Cars!
I travel quite a bit, and I know firsthand that finding a good rental car deal can be a challenge, but that’s why I recommend comparing all of your options with Discover Cars.
In short, Discover Cars is a well-known, reputable business that allows you to search for the best deal across companies, and they have the best full-refund cancellation policy I’ve ever seen, valid up to 72, or sometimes even 48, hours prior to your reservation!
Book Here: Discover Cars
Oʻahu
Visiting Other Islands
If you are visiting Oʻahu or heading to another island, check out some of my personal recommendations for Oʻahu, Maui, Kauaʻi, Molokai, Lānaʻi, and Hawaiʻi Island (Big Island) in these separate posts.
If you’re trying to decide which island is right for your visit, check out my overview about each island in the post below.
Read My Separate Post: What is the Best Hawaiian Island to Visit?
What is the Best Time of Year to Visit Hawaiʻi?
The weather in Hawaiʻi can often appear to be warm and beautiful throughout the year, but in my experience, there is a lot more to consider when planning what time of year to visit the islands, such as what island you are considering, what sides of each island do you plan to stay, what activities are you most interested in, the wildlife, and countless other nuanced variables that can all impact the type of trip you can expect to have.
For these reasons, I highly recommend reading through my separate article to not only understand my thoughts regarding the best time of year to come to Hawaiʻi but also what you need to consider based on the time of year that you plan to visit.
Read My Separate Post: What is the Best Time of Year to Visit Hawaiʻi?
10 Best Tours & Excursions on Oʻahu
There are a lot of different tour options to choose from on Oʻahu, but to make it easier to decide, I made a list of my favorite tours because some things simply are better with a local guide!
Read My Separate Post: Best Tours on Oʻahu
Oʻahu
Safety
All hikes in Hawaiʻi should not be compared to trails outside of the islands, and hikers should exercise due caution on every adventure, given that many are extremely dangerous.
By this, I mean that Hawaiʻi is known for hot, humid weather, steep, dramatic, and unstable cliffs, and flash floods, which can occur without warning. Therefore, it is important that you check the local forecast, understand the physical condition of your entire group, and pack sufficient food and water before attempting any adventure.
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