Founder of HawaiiGuide & certified travel expert with 20+ years of experience in Hawaii tourism.
East Oahu Hiking Trails
Best Hiking Trails on Oahu
Ka'iwa Ridge Trail
The Kaiwa Ridge Trail, also known as Lanikai Pillbox Hike, is an intermediate hike that will take you to some of the most stunning views on Oahu’s windward side. Sitting above Lanikai Beach, Kaiwa Ridge Trail has a steady steep grade throughout the climb.
However, if you’re up to it, you will enjoy unbeatable views of the Mokulua Islands, Kailua Beach, and Lanikai Beach when you reach the top. It takes about an hour to 90 minutes roundtrip and you can choose how far up you wish to go. In hand with the steep grade, you will also be walking a trail with a lot of slippery gravel. Some people find the grass beside the trail is safer and the trial worth the effort to reach the stunning vista.
If you aren’t up to the full trek, the first pillbox is only about 20 to 30 minutes away. You can choose to turn around here or travel another 10 minutes or so to reach the second lookout and pillbox. The scenery along the trail offers breathtaking views whether you choose to complete trial another hour along the ridge or not. The trail ends at A’alapapa Street, about a mile from the trailhead.
The drive from Waikiki is about an hour to get to the starting point of the trail. Although the street isn’t named, it is easy to find as it is directly across from the Mid-Pacific Country Club. Parking is limited and located beside the club. The sign can be spotted on the left-hand side of the street.
Whether you are a fitness enthusiast determined to run the trails or more of an ambler, you will find the ideal hiking trails to lead you to the unmatched views of Oahu.
