Hike the Lanikai Pillboxes

Hawaii Pillboxes Trail

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Hiking to the Lanikai Pillboxes is an easy, leisurely walk that offers amazing views of Mokulua Islands and Lanikai beach. This is a dog and family friendly hike.

The Lanikai Pillbox Trail, also known as the Kaiwa Ridge Trail, is a family-friendly hike. The beginning of the trail is steep with loose gravel, but gets more manageable as you climb the trail. The hike is ~1.25 miles one-way and is an out-and-back trail with a 500ft elevation gain. If you’re an early-riser, this is a great hike to do just before the sun rises. The pillboxes offer panoramic views as well as of the Mokulua Islands. This trail allows dogs on a leash if you’re hiking with your four-legged friend(s). After the hike, you can hang out at Lanikai Beach and rent paddleboards, kayaks, or just go for a swim. If you’re like us and are famished after hiking and have some time, head to Cinnamon’s Restaurant for a bite.

Pack List

  • Walking shoes
  • Swimsuit
  • Beach gear
  • Sun block
  • Water
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Activities:

Photography, Hiking

Skill Level:

Beginner

Season:

Year Round

Trail Type:

Out-and-Back

Distance:

2.5 Miles

Elev. Gain:

500 Feet

Rating:

Features:

Dog Friendly
Family Friendly
Romantic
Scenic

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How to Get There

4 months ago

Great hike for sunrise near Kailua

This is an awesome sunrise hike in the Kailua area. If you search Google Maps for "Pillbox Hike," it takes you to the trailhead on The Outbound. There is no parking lot at the trailhead, so you have to park in one of the surrounding neighborhoods. Once you've parked, the trailhead is pretty well marked and is past the entrance to the Mid Pacific Country Club. The hike to the first pillbox is moderate as you gain elevation and need to make your way up an incline filled with rocks and tree roots. Once you make it to the first pillbox, the hike is much easier and very much like a leisurely stroll to the second pillbox and beyond. If you want to do this hike for sunrise, be sure to leave a little early so you can get a seat on one of the pillboxes. Otherwise, you will need to watch the sunrise from somewhere on the trail. Either way, the sunrise is amazing and you should have a great view of the Mokulua Islands and beyond. I did not do it, but the chatter on the trail seemed to indicate that you could make this hike a loop by continuing on the trail and walking along the road it drop you on to back to the trailhead.

4 months ago

5 months ago

Amazing

I hiked this place alone, and as I climbed up, I took off my shirt and only went up in a sports bra, as humidity increases with the elevation. Then again, I did go in a hot August. The views are gorgeous, and you get a 360 view of the mountains and town. There were a lot of gnats when I was there, so I didn't get to stay too long, as I was overwhelmed by bugs no matter where I moved. But I would go back again on another visit. I have no input on where to park, as I took an Uber there. There are a ton of private roads there and a park across the street, so I'm not sure where one would park.

5 months ago

8 months ago

Great Hike Near Kailua

This is a great hike if you have time and are in the Kailua area. There are two trailheads you can park at. The directions for the trailhead on The Outbound put you in a little less crowded neighborhood with more parking, but the hike to the pillboxes is longer. This hike is moderate (it can be a little tough if you're bringing the whole family and/or don't have great shoes for the trail). You'll be walking on roots, rocks, and tackling a decent incline on the way up. Once you make it to the ridgeline, the hike becomes much easier. If you want a shorter hike to the pillboxes, the trailhead is at 21.38847,-157.7222644.

8 months ago

12 months ago

One Of My Favorite Hikes

Great views, best for sunrise, not too crowded during the day on weekdays. Not a difficult hike but comes with amazing views of the water and Kailua

12 months ago

about 1 year ago

Panorama Heaven

A steep but short climb, the pillboxes trail delivers amazing panoramic views at a very low cost. Always a favorite whenever I'm in Hawaii, it doesn't get old. For the beginner it may seem steep and Rocky but any experienced hiker will be up and back in no time. Pack a lunch and enjoy a picnic on top of the cement structures while taking in the view. Watch for broken glass if you remove your shoes.

about 1 year ago

about 1 year ago

Windy

View was good, looking at the bay and the two islands. The east side of the hills were really windy which kept us cool, and lots of people had dogs off leash but didn't cause any issues. Graffiti all over the pill boxes adds something to look at.

about 1 year ago

over 1 year ago

Short yet scenic!

This is a great hike which is short but offers incredible views over Lanikai Beach and the surrounding area. I should have heeded Brooke's warning and gone at sunrise or in the morning - The midday sun made this feel harder than it actually was! :P

over 1 year ago

over 1 year ago

A Favorite

This hike has a few "tough" spots, but overall it's fairly easy and the view is rewarding, especially at sunrise!

over 1 year ago

about 2 years ago

Nice and short hike with a great view!

about 2 years ago

about 3 years ago

Go early for sun rise

about 3 years ago

Added by Brooke Willson

24 years old, currently living in Central Alberta. Having obtained my Social Worker Degree, I am currently employed as a FT Youth Worker and Resiliency Coach at a K-8 school in my home town. Working school hours has its benefits, as I am able to spend every weekend as well as holidays and summer months out adventuring, exploring and traveling. Kayaking, hiking, biking, running, photography and camping are some of my favourite activities. Also living so close to the Rocky Mountains I am blessed with endless trails, scenery and opportunity to explore. With 14 countries under my belt I want to and will continue to explore our beautiful world on an International level.

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