Kaiwa Ridge (Pillbox) Trail

MODERATE 679 reviews
#1 of 3 trails in

Kaiwa Ridge (Pillbox) Trail is a 1.6 mile moderately trafficked out and back trail located near Kailua, Hawaii that features beautiful wild flowers and is rated as moderate. The trail is primarily used for hiking, walking, and trail running and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

1.6 miles
610 feet
Out & Back

dogs on leash


trail running



wild flowers





Great short rocky steep hike along the Ka'iwa Ridge offers great views of Lanikai and Kailua. Near Waimanalo Beach - wonderful white sand and calm water, Lanikai and Kailua Beaches The Kaiwa Ridge Hike is great to go either sunrise or late afternoon short 0.6 mile each way but gains 500 ft so is steep in places with great views along the way - It takes about 30 minutes or less to hike from the trailhead to the top (second) pillbox (elev. 565-ft). Its another 10 minutes to reach the ridge's highest point (elev. 603-ft) marked by a geodetic marker (the small concrete platform with broken surveyor's pole). The "official" trailhead, unmarked, is about 40 feet uphill on a paved, private driveway along Kaelepulu Drive. The driveway is opposite of the Mid Pacific Country Club & Golf Course just before you reach an exclusive, gated community. The first part of the trail is very steep, slippery, and can be confusing, . This trail is undeveloped. The trail is rocky, windy and rewards you with a great view on top of the pillboxes. No guardrails so can be dangerous for young children. Also the trail is very poplular and can be crowded.

1 day ago

Great view! Parking is limited and it gets crowded even on a weekday during low season so best to come really early.

3 days ago

This hike is seriously INCREDIBLE!! Beautiful views the whole way. The only two recommendations I would make would be to (1) leave early and (2) bring LOTS of water. We left later in the day so were very hot, and didn’t have enough water.

3 days ago

great views, pretty crowded

4 days ago

awesome views...a little on the harder side with a 1 year old on your back.

While the app says it’s okay to bring your dogs, please, please, please bring enough water for them!! Several dogs have died on this hike from heat exhaustion and dehydration.

Steep and in the beginning with lots of mud but you can hold on to the fence or trees so you don’t slide back down . After that part it gets more dry and it was pretty hot when I went with my kids (7 and 10). We ran out of water ( hadn’t planned on hiking) and turned around before reaching the top. That being said the view was still quite spectacular! Very well traveled, busy little hike. Will go go back to go all the way up.

12 days ago

Gets steep fast. But the views are incredible!

12 days ago

Gorgeous view, great hike. We did this and Pu’u Ma’Eli, Eli. Kaiwa was definitely easier on the body and still had amazing views. And right next to the beach!

12 days ago

Awesome views and gnarly sunrise!

15 days ago

Absolutely breathtaking views from the top of this hike. Can be slippery when wet, or watch for loose gravel. Well trafficked and quite busy. Best done in the morning to find parking and avoid sun/heat.

17 days ago

I did this trail on a hot August morning...even at 10am it was still hot...have that water ready. If you are going during the summer months..the earlier the better. Wear good shoes! Sneakers are ok, but make sure they have good grip on the bottom. Parts of this trail are rocky and can get steep and slippery, especially going down. I saw a couple people slip on the way back down. Climb up to the bunker roof. You will get your best picture opportunities there. The 360 degree views of the Ko'olau Mountains and Lanikai are breathtaking. I'm going to have to make this a regular stop on my vacations. It's a great work out and you are well rewarded by the views up top.

17 days ago

We chose to go on an especially hot day, so we drank more than usual. Be sure to bring plenty of water and snacks to keep up your energy during the heat!
There is no designated parking, but we were able to find a spot on the roadside in the Lanikai housing area. There was a guard stationed close to the Clubhouse telling people not to go any further.
My kids (5 & 3) came along for the hike and did just fine. It was a little tricky for the youngest, but it’s very doable with a little encouragement and help from an adult!
It was about 1/2 a mile of a walk to the start of the trail, and it was an immediate uphill trek. It was all lose dirt, but there’s a fence line, trees, and a decent rope to help with the climb up. Be VERY careful on the trip back down, though!
There’s no shade, so be prepared for a lot of sun and sweat. The view is so worth it, though! There is an uphill set of boulders with a leveled out area that offers the first view of the oceanfront. It’s a nice place to take a break, and it’s only about 10 minutes from the pillbox.
There’s some cool graffiti on the way up, too! The pillbox itself is interesting, but make sure to climb to the roof to get the best view!
If you bring your dog, be sure to have lots of water! It’s a very dusty trail and the heat can get crazy.

19 days ago

Amazing views. Very heavily trafficked so go early.

25 days ago

Most amazing views from the top. Great hike but have to go early to find parking. Also GPS brings you to trail head but not to where you need to park.

1 month ago

Hiked the entire ridge - amazing views and had the whole trail to ourselves past the pillbox

1 month ago

Little hike w great view

1 month ago

Did the entire loop of 3-Mile. Very pretty views.

1 month ago

Short steep hike but full of great views!

1 month ago


Can be a bit slippery and a lot of people, so be careful.

1 month ago

Be Clean, careful (w fire), Considerate, & conservation-minded. Parking is limited and can be muddy, so plan accordingly.

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