The Fashionable Frequent Flyers

Aloha Travel Fam — Today, I thought it would be a good idea to share with y’all five amazing hikes on the island of Oahu with incredible views. This list includes hikes of varying competencies, and the views on all of these hikes are pretty great (albeit different). After reviewing this list, the choice of how much effort and sweat you are willing to put in for the ultimate reward will be up to you.

1. Kuliouou Ridge Loop Trail

This trial was by far the most difficult, and the most rewarding that I hiked the entire year I was in Hawaii. To be clear, this isn’t the most difficult technical hike; but, I did this trail on one of the windiest days in the winter and the ridge crossing from west to east was probably the scariest 30-45 minutes of my life. One wrong step and your boy would no longer be on this earth. This hike takes on average 4 to 5 hours, taking into account stops for photos. Those 4-5 hours will be the most scenic you will experience. The trail itself is actually pretty overgrown (and I’d recommend wearing pants if you can), but the views, especially when you’re going up the west side, are, without question, the best you’ll see on the island. My favorite thing about this trail is the fact that there is a spot towards the highest point of the mountain that offers a full panoramic view of the island. For that, it’s all worth it! FYI – there’s quite a bit of rope climbing involved so come ready for a full-body workout.

2. Lanikai Pillbox Hike

This is a popular hike on the East Side of the island. It is short, of easy to moderate competence, and offers incredible views of the East Side of Oahu, including the beautiful and scenic Mokes islands. I recommend this hike at sunrise so that you can watch the beautiful sunrise and also avoid the insane heat in the middle of the day. The hike isn’t shaded at all, and is incredibly crowded during peak hours. It takes roughly 30 minutes to the second pillbox and another 30 minutes down. After your hike, you can go rinse off in the ocean off Lanikai beach, which is one of my 5 favorite beaches on the island.

3. Koko Crater Hike

The infamous Koko Head Stairs. Now, in truth, for folks who are active and do a lot of cardio, this hike is only of moderate competence. Think of it as going up the elliptical for 30 mins and that’s pretty much it. If you’re not very active in a cardiovascular sense, this hike will take everything from you. It’s relatively short, but it’s unshaded and it’s a straight incline hike. In total, to get to the top, you walk up over 1,000 flights of stairs. The views at the top are unparalleled. You get a great view of the south side of Oahu, and at sunset (particularly in the winter), you can get to watch the sun go down from up above. It’s really a sight to behold!

4. Stairway to Heaven

For most avid hikers traveling to Hawaii, y’all will likely be familiar with this hike. It is extremely popular and offers incredible views of the island. Hiking up the Haiku stairs, however, is now illegal and if you’re caught doing it, it’ll cost you a $1,000 fine. There is a legal way to get to the same summit (colloquially known as the back way to the stairway to heaven). This hike is a combination of a flat valley hike and a ridge hike and takes about 5-7 hours roundtrip to complete (with photo breaks). If you’re planning to do this hike, make sure that this is the only onerous activity you schedule for the day — It’ll absolutely wipe you out! But, as with most things that take effort, the payoff is absolutely worth it. Check out my review here.

FYI — Apparently there’s talk of the stairway being removed altogether by the State because of the danger it presents. There is some resistance from the local hiking community, but I think ultimately this will happen pretty soon.

5. Chinaman’s Hat

This is an East Side gem that requires you to traverse some water to get to. Most people kayak there, others paddleboard or bodyboard, and when the tide is really low, some will swim. Once you get to the base of the hat, it’s a pretty short and moderate hike to the apex — probably about 30 minutes or so, but the views from the top are indescribable. The cliffs and ocean backdrop are so stunning and well worth the mini-excursion. I personally would recommend a short to the base of the hat, and a quick hike up. Carry a couple of beers in your dry bag and drink them at the summit. The hike isn’t shaded at all, so carry water and lots of sunscreen (especially if you plan to pop a brew or two). If you have a drone, this is an awesome place to capture some footage.