Kailua, Hawaii

Looking for the best hiking in Kailua? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Kailua. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Hiking Spots in and near Kailua

  • Honolulu, Hawaii

    Koko Head Botanical Garden

    5.0
    1.71 mi / 276 ft gain
    Koko Head Botanical Garden is a loop trail offering a hike for the whole family. The trail is wide, well-marked, with minimal elevation gain. Along the loop, the sections are well-marked with information about which regions of the world the vegetation is native to. You can complete the loop clock...
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  • Honolulu, Hawaii

    Makapu'u Point Lighthouse Trail

    4.4
    3.62 mi / 1263.45 ft gain
    If you're looking to get moving and get your heart rate up or want a place to snap great photos, start with hiking to Makapu’u Lighthouse. The lighthouse was built in 1909 on a 600-ft cliff, which overlooks Makapu’u beach. The hike is more of an uphill walk and can be done in sandals unless you’...
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  • Honolulu, Hawaii

    Hike to Pele's Chair

    1.3 mi / 150 ft gain
    Pele, the Hawaiian volcano goddess, is said to have sat here just before finishing her volcanic activity to form Oahu.  She left here and moved on to the islands of Molokai and Lanai.   The hike is only about a mile to the beach.  You start at the parking area for the Makapu’u Lighthouse Trail.  ...
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  • Honolulu, Hawaii

    Alan Davis

    4.5
    Alan Davis is what the locals call it, but the official name is the “Ka’Iwi Scenic Shoreline” and it's known to be a good place to do some cliff jumping because of the easy access, clear water, and poles that are already positioned for jumpers in the rocky shoreline. Park in the same lot that ta...
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  • Honolulu, Hawaii

    Koko Head Crater Trail

    4.5
    1.6 mi / 961 ft gain
    While hiking up the Koko Head trail, don't get too intimidated, there are grandparents and young kids hiking up these tracks. Take a sip of water, muster your mental toughness, and put one foot in front of the other along the rail trail. Once you're moving, there's no way you'll turn back! When y...
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  • Honolulu, Hawaii

    Moanalua Middle Ridge Trail to the Haiku Stairs Peak

    4.0
    11.03 mi / 4849 ft gain
    The ‘back way’ to the ever popular and still somewhat illegal Haiku Stairs, the Moanalua Middle Ridge hike brings plenty of beauty and even more challenges than the path down the Haiku Stairs. To get to the trailhead, park outside the Moanalua Valley Park and the trail begins just after the green...
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  • Honolulu, Hawaii

    Koko Crater Arch via Halona Blowhole Lookout

    4.5
    0.92 mi / 371 ft gain
    Park at the Halona Blowhole lookout and carefully cross the highway.. Walk west, towards Hawai'i Kai, and in a hundred feet or so you will pass mile marker 15, the trail starts on the rocks just past this marker. Carefully make your way up the rocky hill and onto the ridge, here you will find a t...
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  • Honolulu, Hawaii

    Halona Cove

    5.0
    When driving along the Kalonianaole Highway, traveling towards east from Hawai'i Kai, keep an eye out for the Hanola Blowhole lookout... Park at the lookout and walk out towards the highway. It is here, next to the entrance, that you will find a trail heading down into the cove. From the road it ...
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  • Honolulu, Hawaii

    Spitting Cave

    0.27 mi / 161 ft gain
    Spitting Cave is a short loop trail located in Eastern Honolulu, Hawaii near Hanauma Bay. The trail is a little steep and rocky, sturdy shoes are recommended. This is a great location to see the sunset if you'r e near Hawaii Kai during the right time of day. 
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  • Aiea, Hawaii

    Aiea Loop Trail

    5.0
    4.67 mi / 935 ft gain
    Aiea Loop Trail is a 4.8-mile loop in Keaiwa Heiau State Recreation Area, that offers a mix of shaded forest, ridge-line views, and jungle scenery. The trail winds through a mix of eucalyptus, Norfolk pine, and native koa trees. Along the way, you’ll get occasional glimpses of Pearl Harbor and th...
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  • 4204 Diamond Head Road, Hawaii

    Hike to Diamond Head Overlook

    4.0
    1.6 mi / 500 ft gain
    You will start your hike at the bottom of the volcano. The cost to get into the park is 5$ per vehicle or 1$ for a walk-in or taxi. The cost of the park is absolutely worth it. On the way up the mountain you will start on a wide paved path that starts out relatively flat but gets steeper on the w...
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  • Kaaawa, Hawaii

    Crouching Lion Trail (CLOSED)

    4.5
    4 mi / 2000 ft gain
    NOTE: as of April 2021, this trail is closed indefinitely. Please do not attempt to hike on closed trails.  This trail is not for the faint of heart or those easily scared of heights. The crouching lion trail is a 4 mile loop with an elevation gain of 2,000 feet. The elevation gains and losses a...
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  • Pearl City, Hawaii

    Waimano Falls

    4.5
    2.99 mi / 951 ft gain
    This is a fun hike in central Oahu that leads to multiple water falls! Bring some shoes that you don't care about because the trail is muddy and you will definitely get dirty. There is also a cliff diving spot at one of the falls. This hike is just one trail located in the Ewa Forest Preserve. T...
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  • Wahiawa, Hawaii

    Poamoho Ridge Trail

    7.08 mi / 1877 ft gain
    Access: There are two options for accessing the trailhead:  (1) Get a permit from the Division of Forestry and Wildlife Oahu so you can drive the 6-mile dirt road to the true trailhead. The permit provides you car access through the locked gate and is only available on weekends and holidays. You...
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  • Kapolei, Hawaii

    Ko Olina Beach Park Walking Trail

    5.0
    2.86 mi / 118 ft gain
    The Ko Olina Beach Park Trail near Kapolei on Oahu is a great walking path for both tourists and locals looking for a leisurely and scenic coastal walk or run. The trail is beginner-friendly, making it accessible for families and strollers. The well-maintained path, which stretches along the la...
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  • Kapolei, Hawaii

    Secret Beach

    5.0
    0.1 mi / 0 ft gain
    Secret Beach is situated in the Ko Olina resort area in the town of Kapolei on the island of Oahu. The beach is accessed via a short path from the small public parking area between Paradise Cove Beach to the north and Sacred Beach to the south. Just off the beach, there is a small channel that i...
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