Oahu Hikes

Pu'u Ma'eli'eli Trail

East 'Windward' Oahu Region

#9 Rated Hiking Trail on Oahu

This trail is also known as the Kaneohe Bay Pillbox trail and is considered easy enough for beginners. However, it might be better suited to those with a little more stamina as there are some steep inclines to contend with.

It takes between one to two hours to complete the 2.2-mile journey and is pleasant to travel as it is not overly crowded.  It is about 40 minutes from Waikiki to the trailhead at 279 Kahekili Hwy. It is near enough Koolau Shopping Center across from the Valley of the Temples that you can park there and walk to the end of the guardrail along the highway to find the trailhead.

This is an excellent option as it is a shorter hike that gives you excellent views of the windward side of the island. While much of the trail is through a forested area, you will get peeks at the views and come across some lookout points overlooking K-Bay. Your goal is to reach the pillbox to get the full expanse of the bay below. The pillbox is one of many small bunkers/lookouts built by the military in World War II. The pillboxes have the best views on the island.

Pu'u Ma'eli'eli Trail (Kane'ohe Bay Pillbox)

Ehukai Pillbox Hike

North Shore Oahu Region

#7 Rated Hiking Trail on Oahu

For a breathtaking view of Oahu’s North Shore and the Seven Mile Miracle, you’ll want to take the Ehukai Pillbox Hike. This trail is just a mile and a half there and back and takes about an hour to 90 minutes.

However, this is not for the weak of heart, knees, or those with any other physical challenge. Severe inclines are endured for at least 20 minutes, although the first stretch is balanced by shade.

You can enjoy views of the North Shore from here. True to its name the trail features a number of “pillboxes.” You can stand on top of the pillbox to get the best view of coastline including Banzai Pipeline and Sunset Beach.

Ehukai Pillbox Hike

Ka'iwa Ridge Trail (Lanikai Pillbox Hike)

East 'Windward' Oahu Region

#5 Rated Hiking Trail on Oahu

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.

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.

Lanikai Pillbox Hike

Makapuu Point & Lighthouse Trail

East 'Windward' Oahu Region

#3 Rated Hiking Trail on Oahu

If you are seeking a great view of Oahu’s southeastern shoreline - with tall sea cliffs and an azure blue ocean - Makapu’u Point is the location for a panoramic view of the coast. 

Situated on Kalanianaole Highway on the southeastern tip of the island, Makapu’u is on the right side of the highway about 12 miles east of Honolulu, past Koko Head, Hanauma Bay, and Sandy Beach Park.  Makapu’u is a remnant of a volcanic ridge that rises over 600 feet from the ocean.  It is the easternmost point on the island of Oahu.

From the lookout, panoramic views of Manana Island and Black Rock Island can be seen as well as the expansive blue ocean.  On clear days you can see the entire eastern shore of the island and sometimes you may be able to spot the islands of Molokai and Lanai.  This is an ideal place to whale watch in the season.  Look for old WW11 bunkers on the cliff edges – some of the many relics from the war that still exist on Oahu.

Makapu’u Point

Diamond Head (Leahi) Trail

Waikiki & Honolulu Region

#1 Rated Hiking Trail on Oahu

The trail to the summit of Diamond Head (Hawaiian name Le’ahi), near Waikiki, was built in 1908 as part of the U.S. Army Coastal Artillery defense system. 

From the trailhead to the summit of Diamond Head Crater, it is 0.8miles (1.3km) one way, and it is a 560 foot (171m) climb from the crater floor.  Allow 1.5-2 hours for a safe and leisurely round-trip hike.  The trail follows an uneven and at times steep terrain, and caution as well as appropriate footwear are required. 

At the top, there are extensive 360-degree views of Waikiki, Honolulu, and the surrounding area.  From here you can clearly view the bunkers situated along the crater rim that was built in 1915.  There are also sweeping views of the southeastern Oahu coastline towards Koko Head and the offshore islands of Moloka’i, Lana’i, and Maui.  The elevation at the summit is 761 feet (232m).

Effective May 12, 2022, reservations are required to visit, and all visitors parking vehicles in the crater will be required to book in two-hour time slots beginning at 6 a.m. (two consecutive slots can be booked). Walk-in and drop-off visitors will be subject to one-hour entry time slots. Arrival and exit times will be enforced to assure adequate turnover to allow for later arrivals. Park hours and visitor entrance fees are available at Hawaii DLNR.

Diamond Head (Leahi) Hiking Trail