5 Hikes with Amazing Views on Oahu

Hiking on the beautiful Hawaiian Islands is a fantastic way to get some fresh air and enjoy the nature. The lush jungles and valleys present an unparalleled view of nature’s perfection which you can enjoy with every step you take on the hiking trails. There are hundreds of hikes in Hawaii and today we are going to share with you our 5 favorite hikes with an amazing view on Oahu.

1. Makapu’u Point Lighthouse Trail

The Makapuu Point Lighthouse was built in 1909 on a 600-foot sea cliff overlooking Makapuu Beach. The Makapu’u Point trail offers visitors breathtaking views of the island’s coastline. On the trail, you will have a chance to catch a glimpse and take amazing photos of the beautiful red-roofed Makapu’u Lighthouse.

On a clear day, you may even see Moloka‘i and Lana‘i islands from the top of the trail. The offshore islets are wildlife sanctuaries for Hawaiian seabirds, such as the ‘iwa, frigate bird, and tropicbird. This trail is likewise an excellent place to view migrating humpback whales when it is a season (November – May). 

Lengths: 2.5 miles roundtrip.

Location and Parking: A parking area offers access to the trailhead. The park and trailhead are located off of the Kalanianaole Highway (Hwy. 72) at the southeasternmost point of Oahu.

Tips from us:

• Use sunscreen.
• Wear hat.
• Bring binoculars if you are here during humpback whale migrating season (November-May).

2. Lanikai pillbox

The Pillbox Trail (The Ka’iwa Ridge Trail) has become one of the most popular trails on the island because of the picturesque views of Kailua Bay and Ko’olau Mountains, ease of accessibility, and length of the hike. Lanikai Pillbox Hike is ranked intermediate because of the steady steep grade of the uphill climb right from the start of the trailhead.

Lengths: 1.8 miles round trip.

Location and Parking: You can park in the neighborhood by Lanikai beach, and walk uphill towards the golf course. Address: Kailua, HI 96734.

Tips from us:

• Use sunscreen.
• Wear hat.
• sunrise is the BEST time to do this hike because the sun rises in the east and the main view from the pillboxes faces east as well.

3. Olomana Trail

Be aware that this is not kids and dogs-friendly hike. It’s quite technical with lots of bouldering, rope sections, and tree roots to navigate so your mind and body get quite the workout. This trail requires moderate rock climbing. The 2nd and 3rd peaks should only be attempted by those who are experienced climbers! So the hike is quite challenging but once you get to the first peak, the views are incredible.

Lengths: 4.4 miles round trip.

Location and Parking: Street Parking-1/4mi walk through the golf course entrance. Park on Maunawili Rd or Auloa Rd. Address: Loop Rd, Kailua, HI 96734.

Tips from us:

• It is better to head up at sunrise so you can watch the amazing colors in the sky over Lanikai Beach.
• The views of the third peak from the second peak are the best on the trail. So you do not need to finish all three picks to enjoy the perfect view.
• This trail gets very steep near the top and you will have to climb up some rock walls, so be prepared.

4. Wiliwilinui Ridge Trail

The Wiliwilinui Ridge Trail hike on Oahu is a rugged adventure onto the spine of the island. This Hawaii Kai hike is a great intro ridge hike that offers many upsides of Hawaii ridge hiking without the risks (narrow trails, difficult and slippery ascents). The hike begins along a dirt path in the forest that eventually leads to the ridge. The ridge starts with numerous stairs that allow you to gain elevation quick, giving you expansive views of Honolulu. This ridge contains a few steeper climbs, and may require the use of some ropes, but with a little fortitude, you will reach the summit, where you will be rewarded with beautiful views of both sides of the island.

Lengths: 4.5 miles round trip.

Location and Parking: The trailhead is in a gated community, Waialae Iki. There is a guardhouse where the guard will write down your license plate number and give you a parking pass. There are a limited number of passes. Address: Kuliouou – Kalani Iki.

Tips from us:

• Wear clothes that you don’t mind getting dirty.
• If you want to watch the sunset along the ridgeline, you NEED to bring along a headlamp to make your way back down the trail.
• Note that the parking permits are only good during daylight hours.

5. Moanalua/Kamananui Valley Trail

The Moanalua Valley Trail to Haiku stairs hiking route is one of the most adventurous hikes on Oahu. The hike follows the Moanalua Valley Trail before connecting up the Moanalua Middle Ridge, which is the legal ‘backway’ to the Stairway to Heaven (Haiku Stairs) satellite summit.

Overall the hike up the Kamananui Valley Trail was not difficult, but still long enough to provide a good workout with an amazing view as a reward.

Lengths: 10.5 miles round trip.

Location and Parking: You can park at the Moanalua Valley Park, and walk up to the trailhead. Address: 1827-1839 Ala Aolani St, HI 96819.

Tip from us:

• If it has rained any time in the days before your hike, the trail will be very slippery and muddy. So be ready.