Haleigh HendricksonThere are several sought-after pillbox hikes on O’ahu, but none are as spectacular as the Maili Pillbox hike.
Maili Pillbox, more commonly referred to as Pink Pillbox or officially as Pu’u O Hulu Trail, is located on the west side of the island. While Lanikai Pillbox hike is the spot for sunrise, Maili Pillbox takes the cake for the best place to watch the sunset on O’ahu.
The trail is short and manageable for most hikers, making it a popular trail among locals and visitors alike. Though it’s short in distance, Maili Pillbox Trail over-delivers on views of the west shore and expansive Wainanai Mountain Range.
In this guide, I cover what to expect hiking O’ahu’s Pink Pillbox, getting to the trailhead, the best time to hike, and more. I also highlight the best nearby things to do for the ultimate adventure day on the underrated west side of O’ahu.
Hiking Maili Pillbox Trail or “Pink Pillbox” on O’ahu
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Maili Pillbox Hike Stats
Distance: 1.6 miles
Level: Moderate
Type: Out-and-Back
Elevation Gain: 679 feet
Time: 1.5 – 2 hours
Traffic: Heavy
Dogs: Yes
Know Before You Go
Getting to Maili Pillbox
Maili Pillbox is located on O’ahu’s west side. When visiting O’ahu, most people tend to spend their time exploring the shops and beaches of Waikiki or cruising around the laid-back north shore, all the while neglecting the commonly overlooked west side.
While the Pink Pillbox hike is a bit of a way from downtown Waikiki, it’s absolutely worth the road trip. From Waikiki, get on the I-H-1 W. You will stay on this highway until it turns into the HI-93 W.
The HI-93 W takes you all the way to the turn-off for the trailhead, on Kaukama Road.
While the drive to Maili Pillbox can take you any from 45 minutes to 1.5 hours depending on traffic, the drive is one of my favorites on the island. Roll down the windows and enjoy the view of both the mountains and the ocean.
A Note About Traffic
Once you pass the Ko’olina Resort and enter onto the HI-93 W, the flow of traffic drastically decreases. There are many stoplights along the highway that cause major traffic backups, specifically during rush hour.
Make sure to time your trip to the west side, accordingly. Avoid making the trip to Maili Pillbox anytime between 7:30 a.m. and 9:00 a.m., as well as 3:00 p.m. and 6:00 p.m. Likewise, avoid returning from the west side between 3:00 p.m. and 6:00 p.m.
At the end of this guide, I’ve added nearby adventures you can enjoy either pre-hike or post-hike, to help with timing.
Traffic on O’ahu is no joke and you don’t want to spend your day sitting in stand-still traffic when you could be out enjoying the sun and all the island has to offer.
Finding the Trailhead
From the HI-93 W, take a right turn onto Kaukama Road.
While driving on Kaukama Road, look for a dirt trail jutting up the mountain on your right. Usually, cars parked along the side of the road are a dead giveaway of where to start.
There is no designated parking lot for Maili Pillbox, all hikers must look for available parking along Kaukama Road. There is plenty of parking so finding a spot should not be an issue.
If using Google Maps on your phone, searching “Puʻu O Hulu (Pink Pillbox) Trailhead” will take you to the exact location.
Best Time to Hike
There really is no wrong time to hike Maili Pillbox.
Regardless of the time of day, you will be rewarded with views of the turquoise-blue ocean for as far as you can see.
With that being said, the most stunning time of day to be standing atop the pink pillbox soaking in the 360° views is sunset. The pillboxes of Pu’u O Hulu Trail face west, giving hikers front-row seats to watch the sun dip below the horizon.
We have witnessed the elusive green flash several times while enjoying the sunset from Maili Pillbox. If you’re still a skeptic of whether or not the green flash is real, I encourage you to make it your mission to witness one while visiting O’ahu.
The only downfall to hiking Maili Pillbox at sunset is the crowds.
Sunset brings a lot of eager sunset-chasers to the trail. If you want to avoid these crowds, consider hiking mid-week and mid-day. Just know it will be hot, as there is virtually no reprieve from the sun along the trail.
You’ve been warned.
What to Expect Hiking Maili Pillbox Trail
Maili Pillbox is my favorite pillbox hike on O’ahu because it doesn’t just save the best view for last. Much like the Lanikai Pillbox hike, the trail gives hikers views nearly from start to finish.
The trail to Pink Pillbox starts on a dirt path just off the sidewalk. While the first bit of the trail is under tree coverage, it doesn’t take long before it open ups to views of the surrounding valley and coastline.
The trail is steep with obstacles of rocks, tree roots, loose scree, and dirt. Though Maili Pillbox Trail is short, I always recommend wearing proper hiking shoes on any O’ahu trails to make your time exploring more enjoyable.
I’ve included a section below to help you plan what to pack.
The trail is straightforward and follows a switchback pattern to the top. The path gets narrow at times but never technical — surprisingly, Maili Pillbox Trail doesn’t involve any rope sections as most hikes on O’ahu do.
Though the pillboxes at the top of the trail are the main attraction, there are beautiful spots to stop and soak in the views along the way.
Pillboxes
The trail is commonly referred to by its most popular pillbox, the “pink” pillbox, but there are actually several pillboxes on the trail.
You can take your time exploring all of them, or like me, keep an eye out for the least crowded one and pop a squat there.
My favorite view on the Maili Pillbox hike is actually from the pillbox behind the pink pillbox. This angel allows you to snag a picturesque view and photo of the pink pillbox looming over the teal-blue ocean.
If you’re visiting during the months of November-March, you might even be lucky enough to spot whales from the lookout.
Remember not to get so caught up in the view that you forget about the hike back to the car. If you’re keen on hiking Maili Pillbox Trail for sunset, make sure to leave enough time to hike back to the car before nightfall.
A good practice, regardless of your plans, is to always bring along a headlamp — just in case. You don’t want to be stranded on an unfamiliar trail after dark.
Nearby Westside Adventures
Join a Dolphin Boat Tour
The west side of O’ahu is the spot to encounter ocean wildlife.
The west side is teeming with dolphins and sea turtles year-round, and whales during the winter months. While there are many tour operators to choose from, it’s important to support responsible and sustainable companies.
Please consider doing your research before choosing a company as not all companies follow sustainable practices. Dolphin Excursions is a great tour company and one I highly recommend for an ethical and unforgettable experience.
Snorkel at Electric Beach
While Hanauma Bay is perhaps the most famous snorkeling spot on O’ahu, Electric Beach is arguably the best spot on the entire island of O’ahu, thanks to a nearby power plant.
The plant uses two large pipes that run along the ocean floor to discharge warm water (that’s working to cool the plant). This warm water attracts several species of fish and turtles and creates a flourishing environment of teeming wildlife.
The pipes lead swimmers to a great and accessible snorkeling spot. Make sure to check the current and asses the waves before jumping in.
Sunbathe at Yokohama Bay
The most beautiful beach on O’ahu, in my opinion, is Yokohama Bay Beach.
Yokohama Bay is at the northwestern tip of the island. Referred to as “Yokes” for short, is a large white sand beach beautifully framed by the Waianae Mountains. With the beach being so large, there’s plenty of room to spread out and feel like you’re on your own little slice of paradise.
While sunbathing or playing in the waves, make sure to keep an eye out for dolphins and whales in the distance. Yokes is another incredible place to watch the sunset if you decide to head down from Maili Pillbox early.
Grab a Drink With a View at the Beach House by 604
If you’re exhausted from your hike up Pink Pillbox and are just looking to relax, consider swinging by the Beach House by 604 to grab a drink and some food.
While the food is nothing to write home about, the Beach House offers stunning oceanside views that can’t be topped. Again, the restaurant’s patio is a great place to watch the sunset.
What to Pack
While Maili Pillbox Trail is short, it’s still important to be prepared for the hike. Considering bringing along these items for the best hiking experience.
Water
It never fails, we always spot a hiker or two struggling on Hawai’i trails because they didn’t bring adequate amounts of water.
The climate is different, the trails are rugged, and the sun is hot. Show up prepared on all Hawai’i trails with sufficient amounts of water. Even for short trails, never pack less than 1 liter.
My go-to reusable water bottle is a 32 oz. Nalgene. For longer trails, I always opt for a 2-3 liter water reservoir over a single bottle for easier access and larger carrying capacity.
Day Pack
On shorter hikes like Pink Pillbox, it’s easy to think you can just carry your water, phone, etc. However, I still recommend taking a day pack to house all of your things and keep your hands free.
I’ve used several different daypacks but the Gregory Nano Pack is by far my favorite. With just enough structure, the pack feels secure, but not too large, and is the perfect size for day hikes.
Hiking Shoes
A common misconception is that Hawai’i trails will be as nicely maintained or manicured as trails on the mainland. Trails on O’ahu are notoriously rugged and absolutely warrant hiking or trail shoes with good tread.
I’ve tried and loved several different trail running shoes, but my current go-to shoes are the Merrell Antora 3 Trail Running Shoes.
Sun Protection
As I mentioned earlier, the trails on O’ahu heat up quickly and Maili Pillbox is no exception. Make sure to pack reef-safe sunscreen, a sun shirt, a hat, and/or sunglasses. It’s not uncommon for visitors to suffer from heat stroke or exhaustion.
Nothing ruins a trip quicker.
Head Lamp
A headlamp is one of the 10 hiking essentials, recommend to bring along on any hike. If you are planning to hike Maili Pillbox hike for sunset, it’s a good idea to throw a headlamp in your day pack, just in case.
Sometimes we get caught up in the moment, swooning over the sunset that we forget to allot the time to make it back to the car before dark. While you’re probably thinking, I have a cellphone for such instances, a headlamp allows you to keep your hands free and more safely navigate the descent.
If you have any questions about hiking Maili Pillbox, leave me a comment in the box below. Make sure to add the other pillbox hikes on O’ahu to your list as well: Pu’u Ma’eli’eli Pillbox, Lanikai Pillbox, ‘and Ehukai Pillbox.
And, if you’re looking for more things to do on O’ahu, check out my O’ahu guides for all of my favorite trails, adventures, camping spots, and more.
Happy adventuring!
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