Guide to the Lanikai Pillbox Hike in Oahu, Hawaii

There’s so many amazing trails that you can take while visiting Oahu Hawaii but one of the best and most popular is the Lanikai Pillbox hike! The hike is officially called the Kaiwa Ridge trail and is located in the town of Kailua. This trail is a challenging hike that reward you with panoramic views. If you’re up for the challenge we highly recommend coming on this hike for sunrise so you can “attempt” to avoid the crowd and watch the glorious sun rise above the landscape. Like I mention, the Lanikai Pillbox hike actually takes you to TWO colorful graffitied military pillboxes. which you can rest on while you look out at the sun rising over the Mokulua islands. My boyfriend, Jeff and I only stopped at the first one we came across but if you’re the adventurous type, definitely go for both! 

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The start of the trail is located at 265 Kaelepulu Drive right in front of the Mid Pacific Country Club. We highly recommend renting a car through Turo, (a separate post on our review of the app is coming soon) because it is about a 30-minute drive from Waikiki. And Uber was very expensive during our trip.

Also, we suggest coming early as possible to grab a parking spot. The reason is because they are difficult to find and you’ll see many signs saying “no parking”. The area is residential so make sure to be respectful and follow the signs. We did park on the left side of the Main Street, A’alapapa Dr, just a few blocks from the trail head because we noticed other cars doing the same. But please keep in mind that parking tickets for illegal parking may occur. The safest place to park may be near Lanikai Beach which is a 13 minute walk to the trail head.  

To get to the trail in time for sunrise, we set our alarms for 4:30 AM since we were driving from Waikiki but after snoozing our alarms, we didn’t officially start our morning until 5:30am. The highway and streets are very calm at this hour. And as the sun starts to slowly creep up and lighten up the sky, you’ll start to notice your surrounded by beautiful valleys. Make sure to enjoy the ride up and take in all the beauty Oahu has to offer! 


As we were coming down we noticed that a few people were confused on where the trail started. You’ll want to look for this makeshift sign that says Pillbox trail. This sign is near the Mid Pacific Country Club entrance. Just in case, I made sure to take a photo of the trailhead. If you go past the the fencing that you’ll find on Ka’elepulu dr. you’ve gone too far!

The trail is about 1.25 miles long. To hike without stopping will take about 30 to 40 minutes to complete depending on your physical health. But you may spend more time just really taking in those incredible panoramic views like we did!

The hike is steep and uphill and the back. Therefore, you will not be doing a loop unless you continue past the 2nd pillbox. So more than likely, you will literally be coming back down the way you went up! You’ll start to see the challenge right at the beginning with the steepness. Although, there are some ropes to aid you as you climb up!

This trail is considered family friendly you’ll need to consider this if you plan on taking children or a dog. We seen dogs dominate this trail so it’s possible to bring your pup if they’re super active! But keep in mind that they’re aren’t trees to go under for share so heat exhaustion is a huge risk!

If you are not the most physically in shape, don’t worry, you can still get amazing views of right away once you go past the first 10 minutes without having to go all the way to the pillboxes! 

Also, don’t forget to take everything you bring on this trail back home with you. Please take care of the land, respect Hawaii and DO NOT leave any trash behind. 

Lastly, don’t forget to take a moment to yourself to really appreciate the beauty up there! It’s absolutely magical! ✨?

? Packing list for Lanikai Pillbox Hike 

  • Sun Block ☀️ for your entire Hawaiian vacation, pack eco friendly and reef safe sunblock lotion. Sunscreen from an Aerosol can is not the best for the environment!  
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  • Reusable Water bottle ? lots and lots of water! The elevation is about 500 ft with loose gravel so it can be physically draining. There are a few pull offs to step out of the way of other hikers with nice views as well so you can take periodic sips!
  • Good walking shoes ✨ Don’t wear flip flops, there’s a lot of rocks and the trail is steep so keep that in mind and wear secure shoes! During the rainy season, this trail could get muddy so keep that in mind. And don’t bring white shoes because in the summer when it’s more dry, your shoes will get dusty! I learned this the hard way ?
  • Camera ? Bring your camera or a fully charged smart phone. This hike is very picturesque and you’ll want to capture these moments. The cameras that I use is my Iphone 11 pro plus the DJI Gimbal. For the wide angle shots, I use my canon 90d with a wide angle lens.
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  • AllTrails app ? if you are a frequent hiker or are planning to complete  various trails during your vacation to Oahu, you’ll need to download the all trails app! This app will help you find trails and download offline maps of the area you’re hiking just in case you’re alone or need extra guidance! Plus you can track your miles, which is always fun!
  • Flashlights ? if you don’t have your iPhone during the sunrise hike, try to bring a flashlight along!
  • Comfortable leggings or workout set. ? I wore the heck out of this work out set that I got from She-in. I receive so many compliments from it so here is the link to this cute workout set!
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  • Bikini and beach gear. ? You’re only a few minutes from Lanikai Beach! So reward yourself after with a relaxing beach day!
  • Light Jacket ? If you are doing the sunrise hike you will experience some wind. So be prepared and bring a light jacket. I brought a waterproof jacket just in case. This would probably come in handy if you visit Oahu during the winter time!

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If this blog post was helpful, please feel free to share it! Also, if you have any other questions about the trail, you can find me directly on Instagram at @kristinakayla! Don’t be shy and ask away! I’m always willing to help a fellow traveler! 

Ready for more posts to help you plan your trip to Hawaii? Read my other posts on Oahu, Hawaii here!

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