Hikes, just like luau’s and beach hopping, are one of Hawaii’s high priority bucket list items. There are many unique hikes to choose from but for those just getting started, I recommend Lilikai Pill Box Trail. 

One of the great things about Pillbox Trail is that you can get a lot out of a relatively simple hike. While certain parts of the trek can get quite steep, it is pretty short (thirty minutes up and thirty minutes down) and delivers a stunning view. 

The titular “pillbox” is an old, abandoned blockhouse currently covered in colorful graffiti and murals. There are two of them (the furthest one slightly higher up than the other) and both make for amazing Instagram shots. The pillboxes overlook Lanikai coast — a beautiful stretch of land sprinkled with gorgeous beach homes. At the end of the hike you can see ocean all around — it’s truly a stunning picture. While views from the Pillbox Trail are spectacular any time of the day, I recommend getting there right before sunrise. My group woke up at 4:30 am, drove an hour to Lanikai and started the trek up around 5:30am. It was a bit daunting navigating the first few minutes in darkness (bring a flashlight!) but once we got some sunlight, the rest of the trip was a breeze. A lot of people show up for sunrise, so it may take a bit of maneuvering to find the best spot to watch its start. We decided to hike up a bit further to secure a place on the higher pillbox — and just in time watch the suns light peak over the horizon. It was a very serene experience and super rewarding. 

The trek back down can be a bit tricky (especially if you came in normal walking shoes like I did!). The sand is loose in some areas, offering very little friction. Take your time, and you should be fine. The chances are you’ll want a quick bite to eat afterwards; I recommend Sunny Cafe — it’s only a 10-15 minute drive from Pillbox Trail and offers an assortment of delicious açaí bowls, drinks and coffee (healthy too)!

Pricing: Free!

Transportation: You’ll have to drive out to Lanikai but luckily free parking is pretty easy to find in the surrounding neighborhood (at least at 4am in the morning!) 

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