Hiking the ʻAikahi Pillbox Trail (Kalāheo Hills) on Oʻahu, Hawaiʻi
Distance (Roundtrip): 1.0 - 2.6 miles / 1.6 - 4.2 km
The ʻAikahi Pillbox Trail, also known as the Kalāheo Hills, is a little-known secret in Kailua next to other, more popular trails, like the Lanikai Pillboxes and the Oneʻawa Hills.
That being said, hiking to the ʻAikahi Pillboxes is more difficult when compared to these similar trails, but this also depends on which route you choose to hike to the top; hence, the reason why the distance above is so variable.
With that in mind, the first route from the ʻIli ʻĀina Trailhead shown first is the easiest and most popular trail to the top. However, there are two other possible routes to the summit shown at the end, which are both less trafficked in comparison.
ʻAikahi Pillbox Trailhead Parking (ʻIli ʻĀina)
Parking for the ʻAikahi Pillbox Trail via ʻIli ʻĀina is located on ʻIli ʻĀina Street in Kailua. This is the most popular trailhead for the Kalāheo Hills.
That being said, please be quiet and respectful in this residential neighborhood, as too many trails in Hawaiʻi draw too much negative attention because people just don’t understand this.
Google Maps Directions: ʻAikahi Pillbox Trailhead (ʻIli ʻĀina)
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 ʻAikahi Pillbox Trail (ʻIli ʻĀina)
Distance (One Way): 1.3 miles / 2.1 km
The ʻAikahi Pillbox Trail via ʻIli ʻĀina begins at this unmarked trailhead, which is also the same trailhead for the Kalāheo Hills BMX track.
Being the case, it’s important to pay attention to your surroundings when hiking around blind turns on the ʻIli ʻĀina route, or you risk serious injury from a collision.
Generally speaking, most of the different trails via ʻIli ʻĀina head up to the top, but if you follow the directions here, you’ll take the fastest and most straightforward route to the top.
That being said, go left at this first split.
I generally find it easiest to hike around these little jumps.
At the second split, you can follow either direction.
I chose to go right, but the trail to the left may be slightly faster to reach the same place.
At this junction, go left up the hill.
Finally, go right then right to continue up the hill, and the first lookout will be located shortly ahead.
ʻIli ʻĀina Lookout
This first open area at the top of the initial ascent is the ʻIli ʻĀina Lookout.
Here, go right to begin hiking the Kalāheo Hills toward the ʻAikahi Pillbox.
Kalāheo Hills
Upon reaching the ridgeline that traverses the small peaks across the Kalāheo Hills, simply continue hiking toward the towers in the distance, where the pillbox will be found shortly beyond.
Kalāheo Hills-ʻIlimano Junction
At this first split, go left to continue along the ridgeline, as the trail to the left is the route down to the ʻIlimano Trailhead, discussed later in this article.
ʻAikahi Towers
Once at the towers, follow the ridge down the stairs and up the road immediately following.
There will be a small gap on the right side of the road to continue around the fences and out to the ʻAikahi Pillbox just beyond.
ʻAikahi Pillbox (Puʻu Pāpaʻa)
After 1.3 miles (2.1 km) from the ʻIli ʻĀina Trailhead, the ʻAikahi Pillbox Trail ends at this little-known bunker lookout toward Kāneʻohe to the north, the MCBH to the east, and Kailua to the south.
Some other notable places that hikers can see from the top include Mt. Olomana, Puʻu Māʻeliʻeli, and Kualoa Ranch, to name only a few.
ʻAikahi Pillbox Trail (ʻIlimano)
Total Distance (One Way): 0.8 miles / 1.3 km
Kalāheo Hills-ʻIlimano Junction
On the way down the ʻIli ʻĀina route, I chose to go left at the Kalāheo Hills-ʻIlimano junction to hike down to the ʻIlimano Trailhead because I know it to be shorter and faster.
In comparison, the ʻIlimano route is only 0.3 miles (0.5 km) to reach this junction from the ʻIlimano Trailhead, compared to 0.9 miles (1.4 km) from ʻIli ʻĀina Trailhead.
With that in mind, the ʻIlimano route can be a good trail to hike up if you’re not interested in seeing the ʻIli ʻĀina Lookout, but know that it can be more overgrown than the traditional route.
Once at the base of the Kalāheo Hills, go left to reach the trailhead shortly ahead.
Then, it was a 0.25-mile (0.4 km) walk back to the ʻIli ʻĀina Trailhead from ʻIlimano, but I personally find the walk back on the road to be much nicer and faster than hiking back the traditional way.
ʻAikahi Pillbox Trailhead Parking (ʻIlimano)
Should you be interested in beginning from ʻIlimano, parking for the ʻAikahi Pillbox Trail is located on ʻIlimano Street in Kailua, which is the second most popular trailhead for the Kalāheo Hills.
Google Maps Directions: ʻAikahi Pillbox Trailhead (ʻIlimano)
ʻAikahi Pillbox Trail (ʻIli hau)
Compared to the first two trailheads above, the ʻIli hau Street Trailhead is my least-favorite route to hike to the ʻAikahi Pillbox, which is exactly why it’s last in this article.
I say this largely because the ʻIli hau route is more overgrown than the previous two.
ʻAikahi Pillbox Trailhead Parking (ʻIli hau)
Parking for the ʻAikahi Pillbox Trail via ʻIli hau is located on ʻIli hau Street in Kailua.
Again, this is the least-popular trailhead for the Kalāheo Hills, but for the most adventurous person, I thought that I’d include it here.
Google Maps Directions: ʻAikahi Pillbox Trailhead (ʻIli hau)
Hiking the ʻAikahi Pillbox Trail (ʻIli hau)
Distance (One Way): 0.5 miles / 0.8 km
The ʻAikahi Pillbox Trail via ʻIli hau begins at the very end of ʻIli hau Street.
Then, the trail continues around the very far side of this clearing.
At the top of the little hill in the photo above, there’s a small drainage where you will need to go left to continue on the correct trail.
Once at the water tank, you either have the option to go through the fence here or continue along the outside.
In any case, the ʻIli hau route will continue through the fence in one way or another.
ʻIlihau-Lower ʻAikahi Pillbox Junction
At this less-obvious split in the trail, you can either go right to check out the Lower ʻAikahi Pillbox or left to continue to the upper, more popular ʻAikahi Pillbox.
Back on the ʻIli hau Route
I believe the most annoying part of the ʻIli Hau route is the overgrowth after the junction when continuing to hike up to the main ʻAikahi Pillbox.
When the views begin to open up, the rest of the ʻAikahi Pillbox Trail from this point on is fairly self-explanatory.
Native Plants on the Kalāheo Hills
Since the Kalāheo Hills is a very low-elevation area by Hawaiʻi standards, native Hawaiian plants are few and far between, and the only one that stood out to me was ʻUhaloa.
If you would like to learn more about ʻUhaloa 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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