One of the first hikes (or strolls) that I ever had the opportunity of doing here on Oahu, was the Lanikai Pillboxes, or Kaiwa Ridge hike. By far one of the best hikes on the island for the sheer beauty and photo opportunities that it presents, and the lack of effort and time that it takes to reach your goal. The Lanikai pillbox hike leads to a few World War Two bunkers on the ridge above Lanikai beach. From the ridge top magnificent views present themselves directly in front of you of Waiamanalo, Lanikai and Kailua Beach, and the Mokulua Islands and Flat Island. Behind you is a stunning view of the Koolau Mountains, if the weather is feeling cooperative. This hike is perfect for just about any level of hiker and while you can continue as far along the ridge line as you would like, most people just go to the first or second bunker, which is no more than a thirty minute hike, at the absolute slowest pace possible. The even better thing about this hike is that the gorgeous views come into play after only a few minutes of treking. The trail is incredibly straight forward, and has become exceedingly popular over the years, so don't expect to have it to yourself, all though, it is possible. The one caution is that there is a lot of loose dirt, making the trail a little slippery at times, so I would highly suggest wearing some good sneakers.
This hike is a special one to me for a few reasons. Besides the fact that it was the first hike I did here on Oahu and was a big reason why I got so into adventuring, it was also the spot where I proposed to my wife over three years ago. I don't visit as much as I use to, but it is another one of those places that I always take my friends and family to who are visiting from the mainland. Nothing is better than to take a quick hike up this ridge to admire the views and then to head back down and just across the street to lanikai beach for some swimming with the gorgeous twin islands as an idyllic island paradise backdrop. While this is not exactly an adventure or what I could call an exciting hike, it will however make for an incredibly relaxing day and some great photos and fantastic memories. This is also one of the best spots on the island to catch a sunrise. Since it can get pretty crowded up there for sunrise, I usually just watch it from Lanikai Beach, but if you are willing to head up there early enough, you will most likely be greeted with a sunrise you will never forget.
Directions: Take Kalanianaole Highway heading towards Kailua. Take a right onto Kailua Road, heading into Kailua town. At a T-intersection and traffic light, turn right onto Kalaheo Road. You will then pass Kailua Beach park, eventually turning left to stay along the shoreline and will enter Lanikai. Follow the right fork onto Aalapapa Drive and take a right onto Kaelepulu Drive. You will drive just past the Mid Pacific Country Club golf course, and park in the pullout area on the right side. Parking is sometimes full there and when it is I park in the golf course at the bottom, just off the street where there is usually no other cars. I have been doing this for years, and have never had a problem and the golf course employees will even usually wave to me as I am coming and going. If you do park in there lot, you are doing so at your own risk, but I am just telling you my experiences. After parking walk to the end of the road where there is a gated community. Just before the gated community take a left and walk down the gravel road briefly. There will be a trailhead sign and the trail starts on the far right side by heading steeply uphill. The trail is well defined and easy to follow the rest of the way.