Looking for information on the Lanikai pillbox trail? Read on for all of the details you need to know about Oahu’s most popular and recognizable hike.
Lanikai Beach on the east side of Oahu is one of the world’s most beautiful coastlines. White sandy beach, clear blue water, and two iconic twin picturesque islands called Mokulua Islands or “The Mokes” sit directly offshore.
For a bird’s-eye view of this beautiful shoreline in under an hour hike, a trip to the top of the Kaiwa Ridge is a must-do.
Sitting atop Kaiwa Ridge are two iconic pillboxes, former WWII bunkers that remain nestled and somewhat hidden in the mountainscape.
It’s a relatively short climb to the pillboxes; however, if you’re not accustomed to hiking in Hawaii, it may be a different landscape and significantly harder an ascent than what you are used to.
This is a steep, dry trail that can be slippery and requires scrambling. If there has been recent rain, the terrain will be wet and slippery.
This trail is best hiked at sunrise, when you can see the sun rising in the east. During the day, it remains a beautiful trail but is extremely sun-exposed with no shade.
I worked as a traveling speech pathologist on Oahu for many years and hiked this trail many times. It’s always one of my favorite trails, one I repeat when I come to visit the island, and one I recommend to Hawaii travelers.
Read on to learn more.
Where is Lanikai Pillbox Trail?
Lanikai Pillbox is in the Lanikai Beach neighborhood of Kailua. The trailheads are on residential streets in the community.
This hike is:
- 2.0 miles or about a 10-minute drive from the center of Kailua
- 17 miles or 30-45 minutes from Waikiki, pending traffic
- 35 miles or around 50-60 minutes from the west side of Oahu
There are two different trail heads you can use for the trail. Both will take you to the iconic pillboxes.
If this is your first time doing this hike, I recommend taking the front way. If you use AllTrails for your directions, the trail is labeled as “Lanikai Pillbox #1.”
The trailhead is on a road across from the golf course. When you park in Lanikai, you want to walk towards the golf course, and you’ll see signs guiding you towards the entrance.
The back way, which is labeled on AllTrails as “Lanikai Pillbox #2,” is longer and overgrown, and I wouldn’t recommend it to any first-timers on this hike. For the purpose of this post, I’m only going to talk about parking and directions for “Lanikai Pillbox #1”.
The trail head address is
265 Kaelepulu Dr, Kailua, HI 96734
Where to Park?
Parking is a considerable challenge for this trail. This is one of the hardest trails to find parking for on Oahu. Parking is street parking; there is no parking lot. However, the Lanikai neighborhood has limited parking, with strict enforcement.
Before leaving your car, read the parking sign at your parking spot to ensure you are following the street’s parking regulations.
The parking situation in Lanikai continues to change. At the time of this writing in 2026, parking bans are in effect on weekends and holidays from 10 pm to 6 am. Parking is also prohibited on most of Mokulua and Aalapap Drive from 10 am to 4 pm.
Parking violations are so heavily enforced in Lanikai that even its Wikipedia page goes into detail, warning visitors to be careful.
Per their Wiki page, you cannot park within 4 feet of a driveway, 30 feet of a stop sign, 10 feet of a fire hydrant, or 20 feet of a crosswalk.
If street parking is not possible, try Kailua Beach Park, about a mile from the trailhead, and walk or call an Uber.
You may also want to consider parking in Kailua town center, Ubering to the hike, and then Ubering back to downtown Kailua to grab breakfast or lunch afterward. Kailua town center offers free 3-hour self-parking at many lots, with some paid parking lots.
Again, this trail is best done early to avoid the daytime parking restrictions.
How Long and Difficult is The Pillbox Trail?
The entire trail, round trip to both pillboxes, is around 1.6 miles, and you can easily do it in under an hour.
From the start of the trail to the first pillbox is around 0.7 miles with 232 feet of elevation gain.
Once you get to the first pillbox, it’s another 0.1 mile to get to the second pillbox.
You will easily see the second pillbox from the first one, they sit next to each other.
The trail is rated as HARD by AllTrails, and I tend to agree with that from a mobility standpoint. This is not a trail that you can just walk; it’s a trail that you mix walking with scrambling.
While this may sound easy, it is somewhat challenging.
The ridge is generally dry and dusty, and you have to climb up and down rocky formations with poor traction and no shade. If there was recent rain, it will be muddy and slippery.
At the top of the trail, you can sit on top of or inside the iconic pillboxes, which are cooler when you’re inside the bunker. However, the rest of the trail is exposed to the sun.
What to Bring on The PillBox Trail?
Even though it’s a heavily trafficked, short trail, I recommend coming prepared. I see many people on this trail completely empty-handed, not even with a water bottle, which seems ill-prepared.
My Recommendations:
- Water
- Shoes with a good tread – trail runners are perfect
- Sun protection: hat, sunglasses, and sunscreen
- Phone with a trail map. I use AllTrails+, but you’ll have reception on this trail, so you can even use Apple Maps or Google Maps if you get lost.
- First aid kit in case you have a fall or scrape yourself on the rocks on the trail
I didn’t include trekking poles on this list because I don’t think they are appropriate for this trail and are more of a burden. Given the way the hike is, you’ll likely have to get on all fours to ascend or descend the trail, and trekking poles may make that cumbersome.
If you have trekking poles that can fold up and be stored while you are scrambling, they may be okay.
Also, while the trail is technically dog-friendly, I wouldn’t recommend bringing a pup on it due to the heat. This is a common trail where dogs experience heat exhaustion.
Lanikai Pillbox Trail Recap
Lanikai Pillbox is a top-ranked trail in Oahu. Its scenic views, despite the relatively short climb, make it a popular hike with locals and tourists alike.
Go early to avoid the sun and parking woes.
Enjoy the trail.
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I only share trails that are on public land and maintained for safe use.
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