The top of the 1st peak!

Parking & Trailhead

The hike is located in Kailua and parking can be difficult to find. Luckily, one of my girlfriends lives in Kailua and we parked at her house and walked to the trailhead. The trailhead is on Loop Road, but you’re not allowed to park here. They’re pretty sharp with towing away cars here so don’t try to sneak in. I would recommend parking on Maunawili road however it can get packed on the weekends so your next option is Lunaai St. As you walk up Loop Road, you’ll pass a security guard, this is because the hike is on Royal Hawaiian Golf Club property. However, the hike is legal and you are allowed to be here so don’t worry about the legality of the hike. The guard will probably ask you if you’re doing the Olomana Hike (especially if you’re dressed for it,) so make sure to greet him and reassure him that you’re there for the hike. When I did this hike, he gave us directions on how to find the trailhead from that point, but if he doesn’t that’s ok because it’s easy to find anyway. You’ll have to walk about half a mile down the road from that security checkpoint to find the “Olomana Trailhead” sign on the left. The trail is easy to follow from here.  

Once we reached the 1st peak, we really wanted to take a rest.

Trail Information

This hike can be very muddy, especially after raining, so wear the proper footwear that’s ok with being slightly destroyed. I would recommend wearing athletic leggings because you’ll be sweating so much that chafing becomes a concern – and discomfort. Bring a full jug of water and bring a backpack to carry it in because you’ll want both hands free for this hike.  Sun protection isn’t that necessary because most of the hike is shaded. I like to wear a cap just to keep my hair out of the way.  

I only ventured to the first peak because I’m not that hard-core and neither are my friends. However the views on the first peak are unbelievably rewarding, so don’t feel pressured to make it all the way to the 3rd peak for those views. From the first peak you can see the other two peaks and that’s where the real danger is. The 3rd peak requires you to pass by a wind tunnel that can easily blow you off – quite literally. When I say the phrase “blow you off,” I don’t mean off course into another direction, I mean off the mountain into death. So in other words, be careful. This is a dangerous hike.  

This hike demands a lot more physical strength than it does strategy. If you’ve ever done Koko Head Stairs (refer to my other blogs,) this is definitely similar in that your ascent is physically demanding. There’s only some “climbing” at a few points but there are ropes to help you get stability.

You’ll definitely want to take a break once you reach the 1st peak.

Summary

Overall the hike is worth it because the view from the 1st peak is incredible and hiking Olomana is something to brag about.