Although we’ve completed this hike multiple times, we tend to forget to bring our nice cameras to document the adventure. Many times, we do it without preparation, a last minute exercise, which is why it has taken us much effort to finally include this on our blog. (It really should have been our first hiking post) Without further due, we would like to present our favorite hike on Oahu! It’s not the easiest, it’s not the most beautiful scenery (although better than most “easy” hikes) when hiking however, for a brief time in our lives we hiked this one almost once a week as it was a 10 minute drive from my old living situation: Welcome to Kaiwa Ridge Trail or better known as the Lanikai Pillbox Hike.


Just recently, parking has become much more difficult but there are numerous spaces throughout Lanikai loop on the street. The turn for the hike is the first street on the right. Lanikai is a giant loop so if you get lost or drive too far it’s quite easy to gain your bearing. This sign (a new sign)/entrance to the hike is located across Mid Pacific Country Club. The most obvious giveaway to the hike is the numerous hikers you’ll see walking up or down the road, leading to this sign.




It was our first time bringing Blitz (brown dog). It’s a great hike that’s pet friendly and kid friendly whether your child hikes up on their own or is carried by mom or dad. There are really only about two “difficult” spots, one is at the very beginning as it’s a fairly steep climb, sometimes (depending on the terrain and recent weather) can be very slippery to the point where you need to use your hands to help pull you up. The second spot is right before you get to the first pillbox where it gets very step again. Other than that, you don’t need to be in optimal health to trek this trail as long as you bring water and maybe some sunscreen!





The view is always gorgeous, rain or shine, sunrise, midday or sun set. It’s located on the East side of the island so sunrise hikes are really magical here!






The first pillbox.




On top the second pillbox.





The view from inside the second pillbox. Here you see “The Mokes”. More about The Mokes and how you can kayak to them here.


View from on top of the second pillbox.



Don’t forget to bring enough water for everyone hiking! Of course it always depends on the weather for how much water to bring but we recommend at minimum 32oz/1L (two water bottles).


View looking back at the trail shows Enchanted Lake, Kailua/Kailua Beach, and Kaneohe Marine Corpes Base Hawaii.


The trail for another day…the ridge trail continues down into either Enchanted Lake or the end of Kailua, we haven’t completed it fully just yet but one day soon we will and will be sure to update this post or create it’s own post dedicated to the extension of this trail.


This hike is actually classified as one of the easiest hikes on Oahu. That being said, be sure to bring water, sun protection and always know your limits. Again, this is a kid friendly and pet friendly hike that everyone visiting and living on Oahu should do at least once in their lifetime. It’s the perfect spot to take pictures and view a Hawaii Sunrise. After you hike Lanikai for sunrise, head over to Cinnamon’s for a place to eat (red velvet pancakes!), go to the beach, and end the day with a sunset hike on the West Side.

Lanikai Pillboxes Hike 
Kaelepulu Dr.
Kailua, HI 96734



  1. Dan Scroggins

    These are stunning pictures guys, love the one of MaryRose through the pillbox window and the one of your son climbing out of pillbox. Great work! Aloha \m/