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Trip Planner:   USA  /  Hawaii  /  Oahu  /  Kailua  /  Pillbox Hike

Pillbox Hike, Kailua

4.6
#3 of 8 in Parks in Kailua
Hiking Trail · Hidden Gem · Nature / Park
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Pillbox Hike is located in Kailua. A visit to Pillbox Hike represents just the start of the adventure when you use our Kailua travel route planner to plot your vacation.
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Pillbox Hike reviews

Rate this attraction
TripAdvisor traveler rating
TripAdvisor traveler rating 4.5
931 reviews
Google
4.8
TripAdvisor
  • This hike is overrated. It's more difficult than anticipated. Parking is a nightmare. You have to walk up a narrow private street with no sidewalk to get to the trail head. The best bet is to... 
    This hike is overrated. It's more difficult than anticipated. Parking is a nightmare. You have to walk up a narrow private street with no sidewalk to get to the trail head. The best bet is to...  more »
  • Great hike to do to start off your vacation in Oahu!! I have some experience hiking, am active, and loved every part of this hike! Definitely recommend wearing hiking boots or something with grip... 
    Great hike to do to start off your vacation in Oahu!! I have some experience hiking, am active, and loved every part of this hike! Definitely recommend wearing hiking boots or something with grip...  more »
  • I love this hike so much. For relatively little effort, you are rewarded with stunning 360 degree views quickly and then continue along a ridge for seemingly as long as you want (we kept going past... 
    I love this hike so much. For relatively little effort, you are rewarded with stunning 360 degree views quickly and then continue along a ridge for seemingly as long as you want (we kept going past...  more »
Google
  • Absolutely adore this hike. Views are awesome, hike is reasonable, and it's not too crowded. I'd recommend going before sunset as it gets more crowded and warm as the day goes on. The ropes are especially helpful on the way down. I recommend sneakers or hiking shoes, water, and maybe a snack because you'll want to sit at the top and ponder it all while you gaze at the gorgeous views.
  • Amazing hike with great views. It's an easier hike for all levels of physical fitness. Some spots can be challenging and slippery, but I've seen people run up in slips. It takes about 45 min-1 hour but can be longer if you choose to hang out at the top. Great view of Kailua and the ocean. There are several spots you can stop on the way up each with a great view. It does get windy on that side of the mountain. Definitely recommend to anyone visiting the island.
  • We did the Pillbox Hike for sunrise, arriving about 75 minutes before sunrise on a Monday got us the best spot on the second Pillbox for great photos and nobody in front of us. The view was phenomenal and well worth trudging through the dark to get to. Make sure you're wearing hiking shoes, the hike gets slippery at times and you're very close to some dangerous drops.
  • A lovely hike, may feel abit more on the intermediate side for some beginners. Wear comfortable hiking or running shoes, sandals are not appropriate for this terrain. Bring water and snack as it’s important to re-hydrate and replenish electrolytes / sugar. We used hiking poles (recovering from an injury) but in the end happy we had them, as it helped with overall stability and made it so much easier on the trickier sections. Most people didn’t have poles and just scrambled on some sections. The views are stunning as you will see on most propels review photos!
  • Great place to take in the sunrise. Bring a head lamp and give yourself about an hour. Be prepared for a slight crowd, but there are plenty of little places to pull off the path just before the pillbox if you want to be more alone.

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