Explore the most popular trails near Kailua with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

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Kailua, Hawaii Map
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walking
1 day ago

This one was a nice one to do after hiking 11 Plus miles yesterday. The only things you will need to do on this one is bring a pair of sandals and some sunscreen. From the starting point just go over the bridge and turn right then down to the beach loose the sandals, turn left and enjoy the walk.

Lots of activities along the beach Kitesurfing, kayaking, surfing and of course swimming just to name a few.

Muddy, in and out of rivers, forests, all kinds of trees and flowers with a beautiful waterfall at the end! Not very physically difficult but it is slippery and that can slow you down a bit, increasing time to about 3-4 hours. So worth it! One of my favorites

My favorite to do with my kayaker with a Hobie mirage. Go out and bring a lunch and something to drink. Enjoy watching the birds nest.

what a great hike! incredible views! wear proper shoes!!!

If you want a hike that gives you views of the ocean and coast and not terribly touristy or hard, this is it.

* Steep from the get go. Bring actual footwear with grip
* Gets windy, people lost hats and shades. I almost did
* Past the second pill box is really overgrown. Bring a machete a wear long pants.

I went to the fourth "pill box" at the 1 mile mark is tiny compared to the first 3. (#1 is by itself, 2 and 3 are together) and after that the trail is really overgrown. I saw some folks ahead of me really struggling so I turned back as I didn't have a machete, or long pants.

Bring long pants and shirt, trail has not been taken care of and you will end up with lots and scraps and cuts from the overgrown brush on the last straight before the water fall. Take the shorter routes if you dont feel like dealing with it

hiking
4 days ago

Lovely 360 views, headed here for sunrise and was still quite busy. The trail on from the pillboxes was pretty quite. It rained while we were there and the path did get pretty slippy and would recommend shoes with a fair amount of grip. Also on the way down there is a lot of small paths branching off so use all trails to get back down. It was a Saturday and there was a guy in a car just before the trail head ensuring people don’t park there but there is plenty of parking along the road further on down.

Awesome hike. We did all three peaks and it took us 5 hours. It was very difficult but worth it. We are in our 50’s and in good shape. No parking near the trail. We have hiked Alaska, Utah, Washington and this ranks way up there with our favorite. It was a little like Hawaii’s Angeles landing.

Great hike & nice cliff jump options at the end.

I’m afraid of heights, so it was slightly challenging to get to the top of the second peak. I decided to skip the third entirely because of my fear. If you’re an avid hiker I’d give it a 6/10 difficulty the rocks made for easy stepping points up. If you’re inexperienced, proceed with caution.. climbing is fun and amazing, but you need to be careful of your footing and be aware where it is slippery. With that being said, some thoughtful hikers just put some new ropes up, I didn’t need them but they are great tools if you don’t hike much. I had a great time and the views were AMAZING! 10/10 will go back for the third peak.

Really great views!

Steep slippery trailhead. Beutjful views from the ridge.

If the trail isnt part of Na Ala Hele, it is not maintained very well.

Challenging, fun. Some rope sections that don’t require climbing experience but some upper body strength.

hiking
10 days ago

Also known as Three Peaks. I recommend bringing a friend if going past the first peak for safety. There is rope to help descend down and to get back up the back of the second peak. Fun hike but a little dangerous past the first peak. Third peak is also difficult but is my favorite spot for pictures on this hike.

Hiked all 3 peaks dec 1. First 45/60 min was very muddy with very slippery mud. Recent rain. If you can make the 1st peak, the 2nd shouldn’t be an issue. The 3rd is extremely visually intimidating from the 2nd. If you commit to the 3rd, the first descent to it from the 2nd looks sketchy/challenging and straight up scary. The going down part is the trickiest. The actual climb up the 3rd is not as bad as it appears from the 2nd peak. If fear of heights come into play or it’s extremely windy, I’d say stop at the 1st peak. Also, this took me 5.25 hours and I did empty my bag (as did many others) to continue to the 3rd. ALSO. If you have a drone, i couldn’t launch due to mag interference on the top of all 3 peaks. I have Mavic pro and carried it the entire climb for nothing. Perhaps launch from lower altitude??? Be safe !

Quick, steep and relatively easy. Sliding mud in a few parts but overall quite simple.

hiking
12 days ago

All trails needs more than just difficulty = Easy, Moderate, or Hard .. as this trail is not "easy" in the typical sense.

Strenuous?: Low
Technical/Treacherous?: High

But a great hike! Really enjoyed and might come back. Note it is closed though, as noted by a big sign right at the entrance. But nobody cares

Fun and quick hike!

Great views of Lanikai. Highly recommend hiking the entire ridge trail instead of the short hike just to the Pill Boxes.

hiking
17 days ago

I wouldnt call it easy.

i love to do this in the evening..wonderful sunset and after a beautiful view of the moon and the sky

A Fun trail with a refreshing surprise at the end !

it was absolutely amazing, most of the people do only the way to the 2nd pillbox for taking selfies so that means the first part there was a lot of people... but after that the hike is totally stunning, the view is awesome and the way is funny because you have a lot of up and downs :)
take enough to drink with you i was happy that i dis that :)

Good hike, did it for sunrise. Well worth the early wake up call!

First class views. We did the full trail (not the out and back) in about 2h 15m including the walk back to the car (15 mins). Some steep sections at the beginning and end but “Moderate” difficulty is an appropriate classification. Limited parking. Small crowds of people at the pillboxes. If you continue on past the pillboxes (2) the trail traffic goes to nearly zero. Take enough water (liter or more). Wear and good shoes (no sandals / slippers) but cleats / spikes are not needed. There are almost no bugs on this trail and if you continue past the pillboxes there is plenty of shade cover from the canopy. Some of the best elevated vantage point ocean views on the planet. Please be respectful of the neighbors and remember basic trail etiquette: hikers going uphill have the right of way and leave no trace.

2018-11–23

Nice trail. Not spectacular for Hawaii but would be a 5 star trail in most states. Muddy and slick with many water crossings. Probably best to just accept that you'll get muddy and wet early on and just plow right in rather than trying to stay clean and dry. Quite a few people out for Thanksgiving day

The trail is very muddy, but overall very fun. The water is very cold, but it is beautiful.

This trail was so much fun! Super muddy and slippery but that’s what spikes are for. The waterfall was RAGING today after a nice rainy weekend. We got to the waterfall around 10am (started hike at 8:30) and had it all to ourselves so definitely try to start early-ish. The swimming hole is cold but so refreshing. Can’t wait to do this one again!!!

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