Most Beautiful Day Hikes in Oahu

Oahu, Hawaii

Hiking in Hawaii is a trip.  If you go on some of the best hikes, you'll be considered to be trespassing and will end up having to pay a hefty ticket.  Rather than support and monetize their beautiful hikes, it appears that the local government wants to avoid the associated risks of the hikes altogether.  Although, I can tell you without a doubt that these hikes are in fact, risky.  Take one bad step or slip, and it could be the end of your life (it already has been for some) - so you’d better respect the hikes, hike in the right weather, and be in the right state of mind/good physical shape. This guide provides some general travel tips for hiking in Oahu as well as a list of the most beautiful day hikes there.

General Travel Tips

• If you’re afraid of heights, do not hike these trails. The last thing you want is to freeze up or make a nervous mistake while you're on some steep ridge. You'll not only put yourself at risk, but you'll also risk the lives of those that would come to help you.

• Check the weather. Do not hike if there's been a good amount of rain - it's too slippery/muddy and super dangerous when you're hiking on a ridge with drop offs on either side.

• If mosquitoes like you, bring insect repellent.

• Bring plenty of water, some food, a phone, and a friend. Let someone know where you're going. Being prepared saves lives.

• Microspikes can be your best friend for muddy sections of the hikes. They don't take up too much space and they provide that little extra level of safety.

• Hiking sticks can be very useful getting up and down many of the trails, but you'll need a backpack that can carry them when scrambling up steep, rocky parts of the trails that require both hands.

• Bring a pair of gloves to hang onto the ropes that will assist you when ascending/descending the ridges. They will provide you a better grip, are easier on the hands, and will feel like a life saver if any of the ropes are a bit wet from the rain.

• Hand and foot placement on sections of these hikes is extremely important.  Due to the nature of the terrain, rocks can be unstable and crumbling, plants can be unrealiable to grab hold of, and you can loose your footing on loose gravel or mud.  You'll want your hands in a good spot in case your feet slip or your feet in a good position in case your hands loose their grip.  Also, lean towards the mountain when ascending and lean backward towards the mountain when descending.  This way, if you slip, you land on your butt or chest rather than tumbling down the mountain head over heels.

Most Beautiful Day Hikes

Tom Tom Trail: Park at the Makapu'u lookout.  Cross the street and hike up and along the fence until you pass through the opening in the fence.  From there, just hike along the ridge for some great views.  The full trail can be up to 6.5 miles roundtrip with 4,000 feet of elevation gain, but you only need to go a few miles and gain a few thousand feet of elevation to get this view. Potential ticket for hiking here.

Pu'u O Kona: Park on Kalaau Place and start on the Kuliouou Ridge Trail.  A few minutes into the hike you'll see your first sign.  Take a right for the ridge trail and head all the way up.  When you reach the top, you can take a very slim ridge trail to your left to get to these views.  This trail is about 5 miles roundtrip with 2,000 feet of elevation gain. Legal hike.

Crouching Lion: Pass Swanzy Beach Park and watch for the 27 mile sign on your left (across the street from the ocean).  Continue up the road until you see a dirt parking area on your right and park there.  Cross the street and head back down the road you came up and watch for signs on your right.  Pass through the second set of signs you'll come across and head on up.  This trail is about 4 miles roundtrip with 2,500 feet of elevation gain. Potential ticket for hiking here.

Pu'u Piei: Just up the road from the parking for Crouching Lion, look for the green cement barrier on your right that's painted with the saying "Aloha It's A Life" and park there.  Cross and head up the street until you see a dirt path on your left with a rope that heads up the mountain.  This trail is about 2.5 miles long with 1,800 feet of elevation gain. Legal hike.

Moanalua Middle Ridge to Haiku Stairs: This 10.5 mile roundtrip hike with 2,500 feet of elevation gain will bring you all the way to the well-known Haiku Stairs without having to dodge any police or security guards.  It's a perfectly legal trail.  Park at trailhead to the Moanalua Valley Trail.  From there, head into the jungle and past the green gate.  Follow this path until you pass 17 concrete slabs.  After the 17th slab, you'll see a trail for the Kulana'ahane Trail, but continue past it further for about 15 feet, look for the dirt trail on your left, and head on up. Ridge hike is legal. Potential ticket for the hiking Haiku Stairs.

Sherwood Beach: This is obviously not a hike, but this beach is voted one of the best beaches in the entire United States and for good reason.  After knocking out each of the hikes above, grab some good Hawaiian food and head to this beach for some rest and relaxation.  This beach is a true gem.

Pali Puka: Park at the Nu'Uanu Pali lookout.  The trail starts from the parking lot that is the furthest to your left when facing the lookout.  The trail is approximately 1 mile roundtrip with 500 feet of elevation gain. Potential ticket for hiking here.